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1
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Koosha S, Alavinia S, Ghorbani-Vaghei R. CuI nanoparticle-immobilized on a hybrid material composed of IRMOF-3 and a sulfonamide-based porous organic polymer as an efficient nanocatalyst for one-pot synthesis of 2,4-diaryl-quinolines. RSC Adv 2023; 13:11480-11494. [PMID: 37063714 PMCID: PMC10091365 DOI: 10.1039/d3ra01164j] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.5] [Reference Citation Analysis] [Abstract] [Grants] [Track Full Text] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/21/2023] [Accepted: 03/23/2023] [Indexed: 04/18/2023] Open
Abstract
As a significant class of synthetic and natural products with multiple biological activities, quinolines are used in medical and electronic devices. In this study, a novel method is presented to synthesize 2,4-diarylquinoline derivatives via a simple one-pot multicomponent reaction between phenylacetylenes, aniline derivatives, and aldehydes in CH3CN using IRMOF-3/PSTA/Cu. Notably, polymer/MOF is stabilized through a reaction between a sulfonamide-triazine-based porous organic polymer [poly (sulfonamide-triazine)](PSTA) and an amino-functionalized zinc metal-organic framework (IRMOF-3). Next, the prepared nanocomposites (IRMOF-3/PSTA) are modified using copper iodide nanoparticles (CuI NPs). Overall, the high product yields, facile recovery of nanocatalysts, short reaction times, and broad substrate range make this process environmentally friendly, practical, and economically justified.
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Affiliation(s)
- Samaneh Koosha
- Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University 6517838683 Hamadan Iran +98-8138380709 +98-8138380709
| | - Sedigheh Alavinia
- Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University 6517838683 Hamadan Iran +98-8138380709 +98-8138380709
| | - Ramin Ghorbani-Vaghei
- Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University 6517838683 Hamadan Iran +98-8138380709 +98-8138380709
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2
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Yang A, Zhang H, Hu C, Wang X, Shen R, Kou X, Wang H. Novel coumarin derivatives as multifunctional anti-AD agents: Design, synthesis, X-ray crystal structure and biological evaluation. J Mol Struct 2022. [DOI: 10.1016/j.molstruc.2022.133747] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/31/2022]
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3
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Ghiai R, Alavinia S, Ghorbani-Vaghei R. Chlorosulfonic acid coated on porous organic polymer as a bifunctional catalyst for the one-pot three-component synthesis of 1,8-naphthyridines. RSC Adv 2022; 12:27723-27735. [PMID: 36320279 PMCID: PMC9516894 DOI: 10.1039/d2ra05070f] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/13/2022] [Accepted: 09/19/2022] [Indexed: 11/21/2022] Open
Abstract
The synthesis of six-membered oxygen- and nitrogen-containing heterocycles has been regarded as the most fundamental issue in organic chemistry and the chemical industry because these heterocycles are used in producing high-value products. In this study, an efficient, economic, sustainable, and green protocol for their multicomponent synthesis has been developed. The one-pot direct Knoevenagel condensation-Michael addition-cyclization sequences for the transformation of aromatic aldehydes, malononitrile, and 2-aminopyridine generate the corresponding 1,8-naphthyridines over a novel mesoporous bifunctional organocatalyst supported cholorosulfonic acid [poly(triazine-benzene sulfonamide)-SO3H (PTBSA-SO3H)] under ambient conditions. The catalyst was used for the formation of 1,8-naphthyridine derivatives for six runs. The current strategy provided a wider substrate range, and short reaction times.
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Affiliation(s)
- Ramin Ghiai
- Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University Hamedan 6517838683 Iran +98(81)38380647
| | - Sedigheh Alavinia
- Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University Hamedan 6517838683 Iran +98(81)38380647
| | - Ramin Ghorbani-Vaghei
- Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University Hamedan 6517838683 Iran +98(81)38380647
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4
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Iron(III) chloride and dialkyl diselenides promoted intramolecular cascade cyclization leading to synthesis of selenophene-fused quinoline based heterocycles. Tetrahedron Lett 2022. [DOI: 10.1016/j.tetlet.2022.153907] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
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5
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Marcheva B, Weidemann BJ, Taguchi A, Perelis M, Ramsey KM, Newman MV, Kobayashi Y, Omura C, Manning Fox JE, Lin H, Macdonald PE, Bass J. P2Y1 purinergic receptor identified as a diabetes target in a small-molecule screen to reverse circadian β-cell failure. eLife 2022; 11:e75132. [PMID: 35188462 PMCID: PMC8860442 DOI: 10.7554/elife.75132] [Citation(s) in RCA: 7] [Impact Index Per Article: 2.3] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/29/2021] [Accepted: 01/21/2022] [Indexed: 12/18/2022] Open
Abstract
The mammalian circadian clock drives daily oscillations in physiology and behavior through an autoregulatory transcription feedback loop present in central and peripheral cells. Ablation of the core clock within the endocrine pancreas of adult animals impairs the transcription and splicing of genes involved in hormone exocytosis and causes hypoinsulinemic diabetes. Here, we developed a genetically sensitized small-molecule screen to identify druggable proteins and mechanistic pathways involved in circadian β-cell failure. Our approach was to generate β-cells expressing a nanoluciferase reporter within the proinsulin polypeptide to screen 2640 pharmacologically active compounds and identify insulinotropic molecules that bypass the secretory defect in CRISPR-Cas9-targeted clock mutant β-cells. We validated hit compounds in primary mouse islets and identified known modulators of ligand-gated ion channels and G-protein-coupled receptors, including the antihelmintic ivermectin. Single-cell electrophysiology in circadian mutant mouse and human cadaveric islets revealed ivermectin as a glucose-dependent secretagogue. Genetic, genomic, and pharmacological analyses established the P2Y1 receptor as a clock-controlled mediator of the insulinotropic activity of ivermectin. These findings identify the P2Y1 purinergic receptor as a diabetes target based upon a genetically sensitized phenotypic screen.
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Affiliation(s)
- Biliana Marcheva
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
| | - Benjamin J Weidemann
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
| | - Akihiko Taguchi
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
- Division of Endocrinology, Metabolism, Hematological Science and Therapeutics, Department of Bio-Signal Analysis, Yamaguchi University, Graduate School of Medicine, 1-1-1YamaguchiJapan
| | - Mark Perelis
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
- Ionis Pharmaceuticals, IncCarlsbadUnited States
| | - Kathryn Moynihan Ramsey
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
| | - Marsha V Newman
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
| | - Yumiko Kobayashi
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
| | - Chiaki Omura
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
| | - Jocelyn E Manning Fox
- Department of Pharmacology, Alberta Diabetes Institute, University of AlbertaEdmonton, ABCanada
| | - Haopeng Lin
- Department of Pharmacology, Alberta Diabetes Institute, University of AlbertaEdmonton, ABCanada
| | - Patrick E Macdonald
- Department of Pharmacology, Alberta Diabetes Institute, University of AlbertaEdmonton, ABCanada
| | - Joseph Bass
- Department of Medicine, Division of Endocrinology, Metabolism and Molecular Medicine, Northwestern University Feinberg School of MedicineChicagoUnited States
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6
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Discovery of novel β-carboline derivatives as selective AChE inhibitors with GSK-3β inhibitory property for the treatment of Alzheimer's disease. Eur J Med Chem 2021; 229:114095. [PMID: 34995924 DOI: 10.1016/j.ejmech.2021.114095] [Citation(s) in RCA: 22] [Impact Index Per Article: 5.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/17/2021] [Revised: 12/27/2021] [Accepted: 12/27/2021] [Indexed: 12/12/2022]
Abstract
The natural product harmine, a representative β-carboline alkaloid from the seeds of Peganum harmala L. (Zygophyllaceae), possesses a broad spectrum of biological activities. In this study, a novel series of harmine derivatives containing N-benzylpiperidine moiety were identified for the treatment of Alzheimer's disease (AD). The results showed that all the derivatives possessed significant anti-acetylcholinesterase (AChE) activity and good selectivity over butyrylcholinesterase (BChE). In particular, compound ZLWH-23 exhibited potent anti-AChE activity (IC50 = 0.27 μM) and selective BChE inhibition (IC50 = 20.82 μM), as well as acceptable glycogen synthase kinase-3 (GSK-3β) inhibition (IC50 = 6.78 μM). Molecular docking studies and molecular dynamics simulations indicated that ZLWH-23 could form stable interaction with AChE and GSK-3β. Gratifyingly, ZLWH-23 exhibited good selectivity for GSK-3β over multi-kinases and very low cytotoxicity towards SH-SY5Y, HEK-293T, HL-7702, and HepG2 cell lines. Importantly, ZLWH-23 displayed efficient reduction against tau hyperphosphorylation on Ser-396 site in Tau (P301L) 293T cell model. Collectively, harmine-based derivatives could be considered as possible drug leads for the development of AD therapies.
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Fu J, Bao F, Gu M, Liu J, Zhang Z, Ding J, Xie SS, Ding J. Design, synthesis and evaluation of quinolinone derivatives containing dithiocarbamate moiety as multifunctional AChE inhibitors for the treatment of Alzheimer's disease. J Enzyme Inhib Med Chem 2019; 35:118-128. [PMID: 31694418 PMCID: PMC6844382 DOI: 10.1080/14756366.2019.1687460] [Citation(s) in RCA: 29] [Impact Index Per Article: 4.8] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 02/03/2023] Open
Abstract
A series of novel quinolinone derivatives bearing dithiocarbamate moiety were designed and synthesised as multifunctional AChE inhibitors for the treatment of AD. Most of these compounds exhibited strong and clearly selective inhibition to eeAChE. Among them, compound 4c was identified as the most potent inhibitor to both eeAChE and hAChE (IC50 = 0.22 μM for eeAChE; IC50 = 0.16 μM for hAChE), and it was also the best inhibitor to AChE-induced Aβ aggregation (29.02% at 100 μM) and an efficient inhibitor to self-induced Aβ aggregation (30.67% at 25 μM). Kinetic and molecular modelling studies indicated that compound 4c was a mixed-type inhibitor, which could interact simultaneously with the catalytic anionic site (CAS) and the peripheral anionic site (PAS) of AChE. In addition, 4c had good ability to cross the BBB, showed no toxicity on SH-SY5Y neuroblastoma cells and was well tolerated in mice at doses up to 2500 mg/kg (po).
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Affiliation(s)
- Jie Fu
- Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, China.,Jiangsu Zeyun Pharmaceutical Co., Ltd, Xibei Town Industrial Park, Wuxi, China
| | - Fengqi Bao
- Jiangsu Zeyun Pharmaceutical Co., Ltd, Xibei Town Industrial Park, Wuxi, China
| | - Min Gu
- Jiangsu Zeyun Pharmaceutical Co., Ltd, Xibei Town Industrial Park, Wuxi, China
| | - Jing Liu
- School of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China
| | - Zhipeng Zhang
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, China
| | - Jiaoli Ding
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, China
| | - Sai-Sai Xie
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, China
| | - Jinsong Ding
- Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, China
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8
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Jiang N, Ding J, Liu J, Sun X, Zhang Z, Mo Z, Li X, Yin H, Tang W, Xie SS. Novel chromanone-dithiocarbamate hybrids as multifunctional AChE inhibitors with β-amyloid anti-aggregation properties for the treatment of Alzheimer's disease. Bioorg Chem 2019; 89:103027. [PMID: 31176237 DOI: 10.1016/j.bioorg.2019.103027] [Citation(s) in RCA: 33] [Impact Index Per Article: 5.5] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/22/2019] [Revised: 05/30/2019] [Accepted: 05/30/2019] [Indexed: 12/18/2022]
Abstract
By connecting chromanone with dithiocarbamate moieties through flexible linkers, a series of hybrids as novel multifunctional AChE inhibitors have been designed and synthesized. Most of these compounds displayed strong and excellently selective inhibition to eeAChE as well as potent inhibition to self- and AChE-induced Aβ aggregation. Among them, compound 6c showed the best activity to inhibit eeAChE (IC50 = 0.10 μM) and AChE-induced Aβ aggregation (33.02% at 100 μM), and could effectively inhibit self-induced Aβ aggregation (38.25% at 25 μM). Kinetic analysis and docking study indicated that compound 6c could target both the CAS and PAS, suggesting that it was a dual binding site inhibitor for AChE. Besides, it exhibited good ability to penetrate the BBB and low neurotoxicity in SH-SY5Y cells. More importantly, compound 6c was well tolerated in mice (2500 mg/kg, po) and could attenuate the memory impairment in a scopolamine-induced mouse model. Overall, these results highlight 6c as a promising multifunctional agent for treating AD and also demonstrate that the dithiocarbamate is a valid scaffold for design of multifunctional AChE inhibitors.
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Affiliation(s)
- Neng Jiang
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China; Department of Pharmacy, Affiliated Tumor Hospital of Guangxi Medical University, Nanning, PR China
| | - Jiaoli Ding
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China
| | - Jing Liu
- School of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China
| | - Xiaona Sun
- Department of Pharmacy, Affiliated Tumor Hospital of Guangxi Medical University, Nanning, PR China
| | - Zhipeng Zhang
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China
| | - Zhongxia Mo
- Department of Pharmacy, Affiliated Tumor Hospital of Guangxi Medical University, Nanning, PR China
| | - Xiao Li
- Department of Pharmacy, Affiliated Tumor Hospital of Guangxi Medical University, Nanning, PR China
| | - Hong Yin
- College of Chemistry & Pharmacy, Northwest A&F University, Yangling, PR China
| | - Weizhong Tang
- Department of Gastrointestinal Surgery, Affiliated Tumor Hospital of Guangxi Medical University, Nanning, PR China.
| | - Sai-Sai Xie
- National Pharmaceutical Engineering Center for Solid Preparation in Chinese Herbal Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang, PR China.
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Thangaraj M, Ranjan B, Muthusamy R, Murugesan A, Gengan RM. Microwave Synthesis of Fused Pyrans by Humic Acid Supported Ionic Liquid Catalyst and Their Antimicrobial, Antioxidant, Toxicity Assessment, and Molecular Docking Studies. J Heterocycl Chem 2019. [DOI: 10.1002/jhet.3465] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/26/2023]
Affiliation(s)
- Muthu Thangaraj
- Department of Chemistry, Faculty of Applied Sciences; Durban University of Technology; Durban 4001 South Africa
| | - Bibhuti Ranjan
- Department of Biotechnology and Food Technology, Faculty of Applied Sciences; Durban University of Technology; Durban 4001 South Africa
| | - Ramesh Muthusamy
- Department of Pharmaceutical Analysis and Quality Assurance; Omega College of Pharmacy; Edulabad, Ghatkesar Telangana 501 301 India
| | - Arul Murugesan
- Department of Chemistry, Faculty of Applied Sciences; Durban University of Technology; Durban 4001 South Africa
| | - Robert Moonsamy Gengan
- Department of Chemistry, Faculty of Applied Sciences; Durban University of Technology; Durban 4001 South Africa
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10
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Ansari MI, Hussain MK, Hajela K. Silica-Impregnated Polyphosphoric Acid Catalyzed an Eco-Friendly Rapid Synthesis of Functionalized Tetrahydroquinolines and Quinazolin-4-ones in Water. ChemistrySelect 2018. [DOI: 10.1002/slct.201703192] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/30/2023]
Affiliation(s)
- Mohd. Imran Ansari
- Medicinal and Process Chemistry Division; CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension; Sitapur Road Uttar Pradesh Lucknow-226031 India
- Department of Pharmaceutical Sciences; University of Maryland School of Pharmacy, PHN706; 20 N. Pine Street Baltimore MD-21201 USA
| | - Mohd. Kamil Hussain
- Medicinal and Process Chemistry Division; CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension; Sitapur Road Uttar Pradesh Lucknow-226031 India
- Department of Chemistry; Government Raza Post graduate College; Rampur 244901 India
| | - K. Hajela
- Medicinal and Process Chemistry Division; CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension; Sitapur Road Uttar Pradesh Lucknow-226031 India
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11
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Ghorbani-Vaghei R, Rahmatpour F, Sarmast N, Mahmoudi J, Shahriari A. DABCO as a green catalyst for the synthesis of pyranoquinoline derivatives. CAN J CHEM 2017. [DOI: 10.1139/cjc-2016-0537] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.9] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
Abstract
In this study, a rapid and convenient synthesis of quinolines was developed. The reaction involves a one-pot synthesis of pyranoquinoline derivatives from aldehyde, malonitrile, and 8-hydroxyquinoline using DABCO as a catalyst at 80 °C in H2O/EtOH as the solvent in good to high yields.
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Affiliation(s)
- Ramin Ghorbani-Vaghei
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
| | - Farid Rahmatpour
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
| | - Narges Sarmast
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
| | - Jafar Mahmoudi
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
| | - Azadeh Shahriari
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
- Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 65174, Hamedan, Iran
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12
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Jadhav SJ, Patil RB, Kumbhar DR, Patravale AA, Chandam DR, Deshmukh MB. Sulfamic Acid Catalyzed Atom Economic, Eco-friendly Synthesis of Novel 7-(Aryl)-10-thioxo-7,9,10,11-tetrahedro-6H
-pyrimido-[5′4′:5,6]pyrano[3,2-c]quinoline-6,8(5H
)-dione and its Derivatives. J Heterocycl Chem 2017. [DOI: 10.1002/jhet.2807] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/11/2022]
Affiliation(s)
- Sunetra J. Jadhav
- Department of Agrochemicals and Pest Management; Shivaji University; Kolhapur 416004 India
| | - Reshma B. Patil
- Department of Agrochemicals and Pest Management; Shivaji University; Kolhapur 416004 India
| | - Digambar R. Kumbhar
- Department of Agrochemicals and Pest Management; Shivaji University; Kolhapur 416004 India
| | - Ajinkya A. Patravale
- Medicinal Chemistry Research Laboratory, Department of Chemistry; Shivaji University; Kolhapur 416004 M.S. India
- Department of Chemistry; Vivekanand College; Kolhapur M. S. India
| | - Dattatraya R. Chandam
- Medicinal Chemistry Research Laboratory, Department of Chemistry; Shivaji University; Kolhapur 416004 M.S. India
| | - Madhukar B. Deshmukh
- Department of Agrochemicals and Pest Management; Shivaji University; Kolhapur 416004 India
- Medicinal Chemistry Research Laboratory, Department of Chemistry; Shivaji University; Kolhapur 416004 M.S. India
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Sirakanyan SN, Hovakimyan AA, Noravyan AS. Synthesis, transformations and biological properties of furo[2,3-b]pyridines. RUSSIAN CHEMICAL REVIEWS 2015. [DOI: 10.1070/rcr4447] [Citation(s) in RCA: 26] [Impact Index Per Article: 2.6] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 11/08/2022]
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14
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Bigdeli MA, Marjani K, Farokhi E, Sheikhhosseini E, Ghazanfari D. Synthesis of Novel Pyrano[2,3-b]pyridines from α,α′-Bis(substituted-benzylidene)cycloalkanones. J Heterocycl Chem 2013. [DOI: 10.1002/jhet.1612] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/12/2022]
Affiliation(s)
- Mohammad Ali Bigdeli
- Faculty of Chemistry; Tarbiat Moallem University; 49 Mofateh Street; Tehran; Iran
| | - Katayon Marjani
- Faculty of Chemistry; Tarbiat Moallem University; 49 Mofateh Street; Tehran; Iran
| | - Elinaz Farokhi
- Faculty of Chemistry; Tarbiat Moallem University; 49 Mofateh Street; Tehran; Iran
| | | | - Dadkhoda Ghazanfari
- Faculty of Science, Department of Chemistry; Kerman Branch, Islamic Azad University; Kerman; Iran
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15
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El-Sayed HA, Said SA, Amr AEGE. Synthesis of some fused heterocyclic systems and their nucleoside candidates. RESEARCH ON CHEMICAL INTERMEDIATES 2013. [DOI: 10.1007/s11164-012-1006-y] [Citation(s) in RCA: 8] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 11/24/2022]
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16
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Majumdar KC, Ponra S, Nandi RK. BF3·OEt2-Mediated 1,3-Hydride Shift Followed by 6π Electrocyclization: An Efficient Route for the Synthesis of Pyridopyrimidine, Pyranoquinoline, and Phenanthroline Derivatives. European J Org Chem 2011. [DOI: 10.1002/ejoc.201101065] [Citation(s) in RCA: 10] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/10/2022]
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17
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Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Friedländer Annulation in the Synthesis of Azaheterocyclic Compounds. ADVANCES IN HETEROCYCLIC CHEMISTRY 2011. [DOI: 10.1016/b978-0-12-385464-3.00002-9] [Citation(s) in RCA: 26] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 12/11/2022]
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18
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Ronco C, Jean L, Outaabout H, Renard PY. Palladium-Catalyzed Preparation of N-Alkylated Tacrine and Huprine Compounds. European J Org Chem 2010. [DOI: 10.1002/ejoc.201001158] [Citation(s) in RCA: 23] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
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19
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Ghosh S, Isaacs L. Biological catalysis regulated by cucurbit[7]uril molecular containers. J Am Chem Soc 2010; 132:4445-54. [PMID: 20210325 DOI: 10.1021/ja910915k] [Citation(s) in RCA: 102] [Impact Index Per Article: 6.8] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/21/2022]
Abstract
We report the synthesis of two-faced inhibitors 1-5 that contain both enzyme inhibitor and cucurbit[n]uril binding domains. The enzyme binding domains of 1-5 bind to the active sites of bovine carbonic anhydrase (BCA) or acetylcholinesterase (AChE) and inhibit their catalytic activities. Addition of CB[7] to BCA*1 and BCA*2 results in the transient formation of the BCA*1*CB[7] and BCA*2*CB[7] ternary complexes that undergo rapid dissociation to form free catalytically active BCA along with CB[7]*1 and CB[7]*2. The on-off cycle can be performed repetitively by the sequential addition of competitive guest 8 and CB[7]. The detailed origins of this on-off switching of the catalytic activity of BCA is delineated by the combined inference of UV/vis catalytic assays, fluorescence displacement assays, (1)H NMR, along with measurement of the fundamental values of K(a), k(on), and k(off) for the various complexes involved. In contrast, addition of CB[7] to AChE*4(4) and AChE*5(4) results in the formation of thermodynamically stable ternary complexes AChE*4(4)*CB[7](4) and AChE*5(4)*CB[7](4) that are catalytically inactive. We highlight some of the advantages and disadvantages of the strategy, based on the direct competition between two receptors (e.g., enzyme and CB[7]) for a common inhibitor, used in this paper to control enzyme catalytic activity compared to the strategy employed by Nature involving the binding of an allosteric small molecule remote from the enzyme active site.
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Affiliation(s)
- Soumyadip Ghosh
- Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA
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20
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Lee HM, Song YH. Synthesis of New 4-Amino-2,3,5,6,7,8-hexahydro-1H-10-thia-9-aza-pentaleno[1,2-b]naphthalen-5-ol Derivatives. B KOREAN CHEM SOC 2010. [DOI: 10.5012/bkcs.2010.31.01.185] [Citation(s) in RCA: 6] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/20/2022]
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Lange JHM, Coolen HKAC, van der Neut MAW, Borst AJM, Stork B, Verveer PC, Kruse CG. Design, Synthesis, Biological Properties, and Molecular Modeling Investigations of Novel Tacrine Derivatives with a Combination of Acetylcholinesterase Inhibition and Cannabinoid CB1 Receptor Antagonism. J Med Chem 2010; 53:1338-46. [DOI: 10.1021/jm901614b] [Citation(s) in RCA: 47] [Impact Index Per Article: 3.1] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/31/2022]
Affiliation(s)
- Jos H. M. Lange
- Solvay Pharmaceuticals, Research Laboratories, C. J. van Houtenlaan 36, 1381 CP Weesp, The Netherlands
| | - Hein K. A. C. Coolen
- Solvay Pharmaceuticals, Research Laboratories, C. J. van Houtenlaan 36, 1381 CP Weesp, The Netherlands
| | | | - Alice J. M. Borst
- Solvay Pharmaceuticals, Research Laboratories, C. J. van Houtenlaan 36, 1381 CP Weesp, The Netherlands
| | - Bob Stork
- Solvay Pharmaceuticals, Research Laboratories, C. J. van Houtenlaan 36, 1381 CP Weesp, The Netherlands
| | - Peter C. Verveer
- Solvay Pharmaceuticals, Research Laboratories, C. J. van Houtenlaan 36, 1381 CP Weesp, The Netherlands
| | - Chris G. Kruse
- Solvay Pharmaceuticals, Research Laboratories, C. J. van Houtenlaan 36, 1381 CP Weesp, The Netherlands
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22
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Jo BS, Song YH. Facile Synthesis of New Dimeric Alkylene-Linked Aminothienoquinoline and Aminothienoquinolinol Derivatives. SYNTHETIC COMMUN 2009. [DOI: 10.1080/00397910902906545] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/20/2022]
Affiliation(s)
- Boung Sun Jo
- a Department of Chemistry , Mokwon University , Daejeon, South Korea
| | - Yang-Heon Song
- a Department of Chemistry , Mokwon University , Daejeon, South Korea
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Song YH, Jo BS. Synthesis of 9-amino-5,6,7,8-tetrahydrothieno[3,2-b]quinoline and 9-amino-5,6,7,8-tetrahydrothieno[3,2-b]quinolin-8-ol derivatives. J Heterocycl Chem 2009. [DOI: 10.1002/jhet.186] [Citation(s) in RCA: 16] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/11/2022]
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24
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Shi DQ, Yao H. Clean synthesis of furo[3,4-e]pyrazolo[3,4-b]pyridine-5-one derivatives in aqueous media. J Heterocycl Chem 2009. [DOI: 10.1002/jhet.224] [Citation(s) in RCA: 13] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/12/2022]
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Abstract
AbstractIn the present paper we describe results on the synthesis and lipophilicity determination of a series of biologically active compounds based on their heterocyclic structure. For synthesis of styrylquinoline-based compounds we applied microwave irradiation and solid phase techniques. The correlation between RP-HPLC retention parameter log k (the logarithm of retention factor k) and log P data calculated in various ways is discussed, as well as, the relationships between the lipophilicity and the chemical structure of the studied compounds.
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Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramolecular domino hetero Diels–Alder reactions of 1-oxa-1,3-butadienes in aqueous medium. Tetrahedron 2009. [DOI: 10.1016/j.tet.2009.06.036] [Citation(s) in RCA: 77] [Impact Index Per Article: 4.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/20/2022]
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Lee HM, Song YH. Synthesis of 10-Amino-5,6,7,9-tetrahydro-1-thia-4,9-diazacyclohepta[f]inden-8-one Derivatives using Schmit Reaction. JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE 2009. [DOI: 10.5012/jkcs.2009.53.3.387] [Citation(s) in RCA: 3] [Impact Index Per Article: 0.2] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/20/2022]
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28
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Shi DQ, Yao H. Facile and Clean Synthesis of Furopyridine Derivatives via Three-Component Reaction in Aqueous Media Without Catalyst. SYNTHETIC COMMUN 2009. [DOI: 10.1080/00397910802656034] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/20/2022]
Affiliation(s)
- Da-Qing Shi
- a College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Organic Synthesis of Jiangsu Province, Soochow University , Suzhou, China
| | - Hao Yao
- b College of Chemistry and Chemical Engineering, Xuzhou Normal University , Xuzhou, China
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29
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Shi DQ, Yang F, Ni SN. A facile synthesis of furo[3,4-e]pyrazolo[3,4-b]pyridine-5(7H)-one derivatives via three-component reaction in ionic liquid without any catalyst. J Heterocycl Chem 2009. [DOI: 10.1002/jhet.103] [Citation(s) in RCA: 31] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/11/2022]
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30
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Synthesis of New Alkylene-Linked Donepezil-Aminothienoquinoline Hybrid Related Derivatives. B KOREAN CHEM SOC 2009. [DOI: 10.5012/bkcs.2009.30.4.969] [Citation(s) in RCA: 7] [Impact Index Per Article: 0.4] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/20/2022]
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31
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Marco-Contelles J, Pérez-Mayoral E, Samadi A, Carreiras MDC, Soriano E. Recent Advances in the Friedländer Reaction. Chem Rev 2009; 109:2652-71. [DOI: 10.1021/cr800482c] [Citation(s) in RCA: 505] [Impact Index Per Article: 31.6] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 12/15/2022]
Affiliation(s)
- José Marco-Contelles
- Laboratorio de Radicales Libres y Química Computacional (IQOG, CSIC), Madrid, Spain, Departamento de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia (UNED), Madrid, Spain, and iMed.UL, Research Institute for Medicines and Pharmaceutical Sciences, Faculty of Pharmacy, University of Lisbon, Av. Forcas Armadas, 1600-083 Lisbon, Portugal
| | - Elena Pérez-Mayoral
- Laboratorio de Radicales Libres y Química Computacional (IQOG, CSIC), Madrid, Spain, Departamento de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia (UNED), Madrid, Spain, and iMed.UL, Research Institute for Medicines and Pharmaceutical Sciences, Faculty of Pharmacy, University of Lisbon, Av. Forcas Armadas, 1600-083 Lisbon, Portugal
| | - Abdelouahid Samadi
- Laboratorio de Radicales Libres y Química Computacional (IQOG, CSIC), Madrid, Spain, Departamento de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia (UNED), Madrid, Spain, and iMed.UL, Research Institute for Medicines and Pharmaceutical Sciences, Faculty of Pharmacy, University of Lisbon, Av. Forcas Armadas, 1600-083 Lisbon, Portugal
| | - María do Carmo Carreiras
- Laboratorio de Radicales Libres y Química Computacional (IQOG, CSIC), Madrid, Spain, Departamento de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia (UNED), Madrid, Spain, and iMed.UL, Research Institute for Medicines and Pharmaceutical Sciences, Faculty of Pharmacy, University of Lisbon, Av. Forcas Armadas, 1600-083 Lisbon, Portugal
| | - Elena Soriano
- Laboratorio de Radicales Libres y Química Computacional (IQOG, CSIC), Madrid, Spain, Departamento de Química Inorgánica y Química Técnica, Facultad de Ciencias, Universidad Nacional de Educación a Distancia (UNED), Madrid, Spain, and iMed.UL, Research Institute for Medicines and Pharmaceutical Sciences, Faculty of Pharmacy, University of Lisbon, Av. Forcas Armadas, 1600-083 Lisbon, Portugal
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Shi F, Zhou D, Tu S, Shao Q, Li C, Cao L. An efficient microwave-assisted synthesis furo[3,4-b]-[4,7] phenanthroline and indeno[2,1-b][4,7]phenanthroline derivatives in water. J Heterocycl Chem 2008. [DOI: 10.1002/jhet.5570450418] [Citation(s) in RCA: 14] [Impact Index Per Article: 0.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/10/2022]
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A novel and efficient one-pot synthesis of furo[3′,4′:5,6]pyrido[2,3-c]pyrazole derivatives using organocatalysts. Tetrahedron 2008. [DOI: 10.1016/j.tet.2007.12.053] [Citation(s) in RCA: 73] [Impact Index Per Article: 4.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
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Małecki JG, Kusz J, Kruszynski R, Tabak D, Mazurak Z. The reaction between [RuCl2(PPh3)3] and hydroxyquinoline carboxylic acid. Struct Chem 2008. [DOI: 10.1007/s11224-007-9280-9] [Citation(s) in RCA: 5] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/22/2022]
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Tu SJ, Zhang Y, Jiang H, Jiang B, Zhang JY, Jia RH, Shi F. A Simple Synthesis of Furo[3′,4′:5,6]pyrido[2,3-d]pyrimidine Derivatives through Multicomponent Reactions in Water. European J Org Chem 2007. [DOI: 10.1002/ejoc.200600913] [Citation(s) in RCA: 34] [Impact Index Per Article: 1.9] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/07/2022]
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Abstract
AIM: To understand the correlation of serum cholinesterase (CHE) activity with gastric cancer and to assess their clinical significance.
METHODS: The velocity method was adopted to detect the activity of serum CHE in patients with gastric cancer and in patients with non-malignant tumor as controls.
RESULTS: The serum CHE activity in the treatment group was significantly lower than that in the control group with a very significant difference between the two groups (83.3:113.1,P = 0.0003). Age was significantly associated with the incidence of gastric caner.
CONCLUSION: Serum CHE activity has a close relation with the incidence of gastric cancer.
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Affiliation(s)
- Shan-Zhi Gu
- Key Laboratory of Environment and Genes Related to Diseases of Ministry of Education, Medical College of of Xi'an Jiaotong University, Xi'an 710061, Shaanxi Province, China
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