(2S)-2-amino-N-(5-(2-(methylamino)pyridine-4-yl)-1,3,4-thiadiazol-2-yl)-3-phenylpropanamide | 1240521-60-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-amino-N-(5-(2-(methylamino)pyridine-4-yl)-1,3,4-thiadiazol-2-yl)-3-phenylpropanamide
• 英文别名: (2S)-2-amino-N-[5-[2-(methylamino)pyridin-4-yl]-1,3,4-thiadiazol-2-yl]-3-phenylpropanamide
• CAS: 1240521-60-1
• 化学式: C₁₇H₁₈N₆OS
• 分子量: 354.436
• InChiKey: HLVFOWCUUAIWIA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  噻唑-4-甲醛 、 (2S)-2-amino-N-(5-(2-(methylamino)pyridine-4-yl)-1,3,4-thiadiazol-2-yl)-3-phenylpropanamide 在 三乙酰氧基硼氢化钠 作用下， 反应 1.0h， 以43%的产率得到(2S)-N-(5-(2-methylamino)pyridine-4-yl)-(1,3,4-thiadiazol-2-yl)-3-phenyl-2-(thiazol-4-ylmethylamino)propanamide
  参考文献：
  名称：

  Phenylalanine derivatives as GPR142 agonists for the treatment of Type II diabetes

  摘要：

  GPR142 is a novel GPCR that is predominantly expressed in pancreatic beta-cells. GPR142 agonists potentiate glucose-dependent insulin secretion, and therefore can reduce the risk of hypoglycemia. Optimization of our lead pyridinone-phenylalanine series led to a proof-of-concept compound 22, which showed in vivo efficacy in mice with dose-dependent increase in insulin secretion and a decrease in glucose levels. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.015
• 作为产物：
  描述：

  tert-butyl ((S)-1-(5-(2-methylamino)pyridine-4-yl)-1,3,4-thiadiazol-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 在 三氟乙酸 作用下， 以52%的产率得到(2S)-2-amino-N-(5-(2-(methylamino)pyridine-4-yl)-1,3,4-thiadiazol-2-yl)-3-phenylpropanamide
  参考文献：
  名称：

  Phenylalanine derivatives as GPR142 agonists for the treatment of Type II diabetes

  摘要：

  GPR142 is a novel GPCR that is predominantly expressed in pancreatic beta-cells. GPR142 agonists potentiate glucose-dependent insulin secretion, and therefore can reduce the risk of hypoglycemia. Optimization of our lead pyridinone-phenylalanine series led to a proof-of-concept compound 22, which showed in vivo efficacy in mice with dose-dependent increase in insulin secretion and a decrease in glucose levels. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.015

文献信息

• PHENYLANALINE AMIDE DERIVATIVES USEFUL FOR TREATING INSULIN-RELATED DISEASES AND CONDITIONS
  申请人：Du Xiaohui

  公开号：US20120115811A1

  公开（公告）日：2012-05-10

  Provided herein are compounds of formula I: wherein A, B, X, R 1 , R 2 and subscript n are as defined in the following disclosure. Compositions comprising the compounds are also provided, as well as methods for their use, for example, in treatment of type 2 diabetes and type 2 diabetes-related conditions.

  本文所提供的是I式化合物：其中A、B、X、R1、R2和下标n如下所述。本文还提供了包含该化合物的组合物，以及使用它们的方法，例如用于治疗2型糖尿病和2型糖尿病相关疾病的方法。
• [EN] PHENYLALANINE AMIDE DERIVATIVES USEFUL FOR TREATING INSULIN-RELATED DISEASES AND CONDITIONS<br/>[FR] DÉRIVÉS DE LA PHÉNYLALANINE-AMIDE UTILES POUR LE TRAITEMENT DE MALADIES ET ÉTATS LIÉS À L'INSULINE
  申请人：AMGEN INC

  公开号：WO2010093849A3

  公开（公告）日：2010-10-28
• US8785468B2
  申请人：——

  公开号：US8785468B2

  公开（公告）日：2014-07-22