N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2-(4-(cyclopropylsulfonyl)-6-methyl-2-oxopyridin-1(2H)-yl)propanamide | 1036208-60-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2-(4-(cyclopropylsulfonyl)-6-methyl-2-oxopyridin-1(2H)-yl)propanamide
• 英文别名: N-(5-chloro-1,3-thiazol-2-yl)-3-cyclopentyl-2-(4-cyclopropylsulfonyl-2-methyl-6-oxopyridin-1-yl)propanamide
• CAS: 1036208-60-2
• 化学式: C₂₀H₂₄ClN₃O₄S₂
• 分子量: 470.013
• InChiKey: IAVMXMUGKVSJRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2-(4-(cyclopropylsulfonyl)-6-methyl-2-oxopyridin-1(2H)-yl)propanamide 生成 (R)-N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2-(4-(cyclopropylsulfonyl)-6-methyl-2-oxopyridin-1(2H)-yl)propanamide 、 (S)-N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2-(4-(cyclopropylsulfonyl)-6-methyl-2-oxopyridin-1(2H)-yl)propanamide
  参考文献：
  名称：

  Design, synthesis and SAR of novel glucokinase activators

  摘要：

  Guided by co-crystal structures of compounds 15, 22 and 30, an SBDD approach led to the discovery of the 6-methyl pyridone series as a novel class of GKAs that potently activate GK in enzyme and cell assays. Anti-diabetic OGTT efficacy was demonstrated with 54 in a mouse model of type 2 diabetes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.093
• 作为产物：
  描述：

  3-cyclopentyl-2-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)propanoic acid 在 硫酸 、 四乙基氯化铵 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二甲基苯胺 、 三乙胺 、 间氯过氧苯甲酸 、 lithium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2-(4-(cyclopropylsulfonyl)-6-methyl-2-oxopyridin-1(2H)-yl)propanamide
  参考文献：
  名称：

  Design, synthesis and SAR of novel glucokinase activators

  摘要：

  Guided by co-crystal structures of compounds 15, 22 and 30, an SBDD approach led to the discovery of the 6-methyl pyridone series as a novel class of GKAs that potently activate GK in enzyme and cell assays. Anti-diabetic OGTT efficacy was demonstrated with 54 in a mouse model of type 2 diabetes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.093

文献信息

• GLUCOKINASE ACTIVATORS
  申请人：Takeda San Diego, Inc.

  公开号：EP2091947A2

  公开（公告）日：2009-08-26
• Glucokinase Activators
  申请人：Cheruvallath Zacharia

  公开号：US20120252814A1

  公开（公告）日：2012-10-04

  Compounds of the following formula are provided for use with glucokinase: wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.
• US8163779B2
  申请人：——

  公开号：US8163779B2

  公开（公告）日：2012-04-24
• US8530499B2
  申请人：——

  公开号：US8530499B2

  公开（公告）日：2013-09-10
• [EN] GLUCOKINASE ACTIVATORS<br/>[FR] ACTIVATEURS DE GLUCOKINASE
  申请人：TAKEDA SAN DIEGO INC

  公开号：WO2008079787A2

  公开（公告）日：2008-07-03

  (EN) Compounds of the following formula are provided for use with glucokinase: Formula (I), wherein the variables are as defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.(FR) L'invention concerne des composés représentés par la formule suivante destinés à une utilisation avec une glucokinase. Les variables sont telles que définies dans les spécifications. L'invention concerne aussi des compositions pharmaceutiques, des kits et des articles de manufacture comprenant ces composés, des procédés et des intermédiaires qui conviennent pour la fabrication de ces composés et des procédés d'utilisation de ces composés.