(S)-2-(4-chlorophenyl)-3, 3-dimethyl–N- (5-phenylthiazol-2-yl) butanamide | 1208552-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-(4-chlorophenyl)-3, 3-dimethyl–N- (5-phenylthiazol-2-yl) butanamide
• 英文别名: (S)-2-(4-chlorophenyl)-3,3-dimethyl-N-(5-phenylthiazol-2-yl)butanamide；Cmp58；(2S)-2-(4-chlorophenyl)-3,3-dimethyl-N-(5-phenyl-1,3-thiazol-2-yl)butanamide
• CAS: 1208552-99-1
• 化学式: C₂₁H₂₁ClN₂OS
• 分子量: 384.93
• InChiKey: ZVAPEFXSRDIMFP-SFHVURJKSA-N

物化性质

• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为产物：
  描述：

  2-氨基-5-苯基噻唑 、 (S)-2-(4-chlorophenyl)-3,3-dimethylbutanoic acid 在 2,4,6-三甲基吡啶 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以23%的产率得到(S)-2-(4-chlorophenyl)-3, 3-dimethyl–N- (5-phenylthiazol-2-yl) butanamide
  参考文献：
  名称：

  The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators

  摘要：

  Free fatty acid receptor 2 (FFA2) is a G-protein coupled receptor for which only short-chain fatty acids (SCFAs) have been reported as endogenous ligands. We describe the discovery and optimization of phenylacetamides as allosteric agonists of FFA2. These novel ligands can suppress adipocyte lipolysis in vitro and reduce plasma FFA levels in vivo, suggesting that these allosteric modulators can serve as pharmacological tools for exploring the potential function of FFA2 in various disease conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.112

文献信息

• METHODS AND COMPOSITIONS RELATED TO TARGETING FFAR2 AND ILC3 POPULATIONS FOR THE TREATMENT OF A GASTROINTESTINAL DISEASE
  申请人：PRESIDENT AND FELLOWS OF HARVARD COLLEGE

  公开号：US20220008368A1

  公开（公告）日：2022-01-13

  Described herein are methods, assays, and compositions and uses thereof related to treating, preventing, and detecting a gastrointestinal disease with an agent that targets Ffar2. The agents described herein can further increase populations of group 3 innate lymphoid cells (ILC3s) in the gut.
• [EN] METHODS AND COMPOSITIONS RELATED TO TARGETING FFAR2 AND ILC3 POPULATIONS FOR THE TREATMENT OF A GASTROINTESTINAL DISEASE<br/>[FR] MÉTHODES ET COMPOSITIONS RELATIVES AU CIBLAGE DE POPULATIONS DE FFAR2 ET D'ILC3 POUR LE TRAITEMENT D'UNE MALADIE GASTRO-INTESTINALE
  申请人：HARVARD COLLEGE

  公开号：WO2020102472A1

  公开（公告）日：2020-05-22

  Described herein are methods, assays, and compositions and uses thereof related to treating, preventing, and detecting a gastrointestinal disease with an agent that targets Ffar2. The agents described herein can further increase populations of group 3 innate lymphoid cells (ILC3s) in the gut.
• [EN] USE OF FFAR2 AGONISTS FOR THE TREATMENT OF BACTERIAL SUPERINFECTIONS POST-VIRAL INFECTION<br/>[FR] UTILISATION D'AGONISTES DE FFAR2 POUR LE TRAITEMENT DE SURINFECTIONS BACTÉRIENNES SUITE À UNE INFECTION VIRALE
  申请人：INST NAT SANTE RECH MED

  公开号：WO2021018786A1

  公开（公告）日：2021-02-04

  Severe influenza is associated with defects in pulmonary innate immunity, a phenomenon leading to secondary bacterial infections. The gut microbiota can control immune/inflammatory responses locally and at distant sites. The inventors hypothesized that perturbation of the gut microbiota during severe influenza might participate in bacterial superinfection. Their data demonstrated that influenza infection profoundly altered the functionality of the gut microbiota as assessed by the altered production of short chain fatty acids (SCFAs). Remarkably, treatment of IAV-infected mice with acetate, the main SCFA found systematically, reinforced host defenses against S. pneumoniae. Lastly, the inventors showed that pharmacological manipulation of the FFAR2 agonist TUG-1375 provides the same benefit as acetate in the treatment of bacterial superinfection post-influenza. The present invention thus relates to the use of synthetic free fatty acid receptor 2 (FFAR2) agonist for the treatment of bacterial superinfections post-viral infection (e.g. post-influenza).
• The first synthetic agonists of FFA2: Discovery and SAR of phenylacetamides as allosteric modulators
  作者：Yingcai Wang、Xianyun Jiao、Frank Kayser、Jiwen Liu、Zhongyu Wang、Malgorzata Wanska、Joanne Greenberg、Jennifer Weiszmann、Hongfei Ge、Hui Tian、Simon Wong、Ralf Schwandner、Taeweon Lee、Yang Li

  DOI：10.1016/j.bmcl.2009.11.112

  日期：2010.1

  Free fatty acid receptor 2 (FFA2) is a G-protein coupled receptor for which only short-chain fatty acids (SCFAs) have been reported as endogenous ligands. We describe the discovery and optimization of phenylacetamides as allosteric agonists of FFA2. These novel ligands can suppress adipocyte lipolysis in vitro and reduce plasma FFA levels in vivo, suggesting that these allosteric modulators can serve as pharmacological tools for exploring the potential function of FFA2 in various disease conditions. (C) 2009 Elsevier Ltd. All rights reserved.