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Zuo Y, Zuo P, Liu M, Wang X, Du J, Li X, Zhang P, Xu Z. Recent approaches for the synthesis of heterocycles from amidines via a metal catalyzed C-H functionalization reaction. Org Biomol Chem 2024; 22:5014-5031. [PMID: 38831700 DOI: 10.1039/d4ob00420e] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 06/05/2024]
Abstract
Transition metal catalyzed C-H bond activation has become one of the most important tools for constructing new chemical bonds. Introducing directing groups to the substrates is the key to a successful reaction, these directing groups can also be further transformed in the reaction. Amidines with their unique structure and reactivity are ideal substrates for transition metal-catalyzed C-H transformations. This review describes the major advances and mechanistic investigations of the C-H activation/annulation tandem reactions of amidines until early 2024, focusing on metal-catalyzed C-H activation of amidines with unsaturated compounds, such as alkynes, ketone, vinylene carbonate, cyclopropanols and their derivatives. Meanwhile this manuscript also explores the reaction of amidines with different carbene precursors, for example diazo compounds, azide, triazoles, pyriodotriazoles, and sulfoxonium ylides as well as their own C-H bond activation/cyclization reactions. A bright outlook is provided at the end of the manuscript.
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Affiliation(s)
- Youpeng Zuo
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
| | - Pengfei Zuo
- Kunshan Customs, Kunshan, Jiangsu 215300, People's Republic of China
| | - Meijun Liu
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
| | - Xiaoqing Wang
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
| | - Jun Du
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
| | - Xiaoling Li
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
| | - Pinghua Zhang
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
| | - Zhenhua Xu
- School of Chemistry and Chemical Engineering, Suzhou University, Suzhou, Anhui 234000, People's Republic of China.
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Cenac N, Andrews CN, Holzhausen M, Chapman K, Cottrell G, Andrade-Gordon P, Steinhoff M, Barbara G, Beck P, Bunnett NW, Sharkey KA, Ferraz JGP, Shaffer E, Vergnolle N. Role for protease activity in visceral pain in irritable bowel syndrome. J Clin Invest 2007; 117:636-47. [PMID: 17304351 PMCID: PMC1794118 DOI: 10.1172/jci29255] [Citation(s) in RCA: 446] [Impact Index Per Article: 24.8] [Reference Citation Analysis] [Abstract] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/25/2006] [Accepted: 12/05/2006] [Indexed: 12/12/2022] Open
Abstract
Mediators involved in the generation of symptoms in patients with irritable bowel syndrome (IBS) are poorly understood. Here we show that colonic biopsy samples from IBS patients release increased levels of proteolytic activity (arginine cleavage) compared to asymptomatic controls. This was dependent on the activation of NF-kappaB. In addition, increased proteolytic activity was measured in vivo, in colonic washes from IBS compared with control patients. Trypsin and tryptase expression and release were increased in colonic biopsies from IBS patients compared with control subjects. Biopsies from IBS patients (but not controls) released mediators that sensitized murine sensory neurons in culture. Sensitization was prevented by a serine protease inhibitor and was absent in neurons lacking functional protease-activated receptor-2 (PAR2). Supernatants from colonic biopsies of IBS patients, but not controls, also caused somatic and visceral hyperalgesia and allodynia in mice, when administered into the colon. These pronociceptive effects were inhibited by serine protease inhibitors and a PAR2 antagonist and were absent in PAR2-deficient mice. Our study establishes that proteases are released in IBS and that they can directly stimulate sensory neurons and generate hypersensitivity symptoms through the activation of PAR2.
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Affiliation(s)
- Nicolas Cenac
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Christopher N. Andrews
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Marinella Holzhausen
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Kevin Chapman
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Graeme Cottrell
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Patricia Andrade-Gordon
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Martin Steinhoff
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Giovanni Barbara
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Paul Beck
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Nigel W. Bunnett
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Keith A. Sharkey
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Jose Geraldo P. Ferraz
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Eldon Shaffer
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
| | - Nathalie Vergnolle
- Department of Pharmacology and Therapeutics and
Department of Medicine, Division of Gastroenterology, University of Calgary, Calgary, Alberta, Canada.
Departments of Surgery and Physiology, UCSF, San Francisco, California, USA.
R.W. Johnson Pharmaceutical Research Institute, Spring House, Pennsylvania, USA.
Department of Dermatology and Interdisciplinary Center for Clinical Research (IZKF) Münster, University of Münster, Münster, Germany.
Departments of Internal Medicine and Gastroenterology, University of Bologna, Bologna, Italy.
Department of Physiology and Biophysics, Faculty of Medicine, University of Calgary, Calgary, Alberta, Canada
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