3-cyclohexyl-2-(2-oxopiperazin-1-yl)-N-(1,3-thiazol-2-yl)propanamide | 1428663-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-cyclohexyl-2-(2-oxopiperazin-1-yl)-N-(1,3-thiazol-2-yl)propanamide
• CAS: 1428663-10-8
• 化学式: C₁₆H₂₄N₄O₂S
• 分子量: 336.458
• InChiKey: SQCOEBZJFCFKNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  间甲苯磺酰氯 、 3-cyclohexyl-2-(2-oxopiperazin-1-yl)-N-(1,3-thiazol-2-yl)propanamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-cyclohexyl-2-[4-(3-methylphenyl)sulfonyl-2-oxopiperazin-1-yl]-N-(1,3-thiazol-2-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：

  N-boc-dl-3-环己基丙氨酸 在 盐酸 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-cyclohexyl-2-(2-oxopiperazin-1-yl)-N-(1,3-thiazol-2-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：Cheruvallath Zacharia

  公开号：US20090099163A1

  公开（公告）日：2009-04-16

  Compounds are provided for use with glucokinase that comprise the formula: 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.

  提供用于葡萄糖激酶的化合物，其化学式为：其中变量如本文所定义。还提供了包含这些化合物的药物组合物、工具包和制造物品；用于制备这些化合物的方法和中间体；以及使用这些化合物的方法。
• US8173645B2
  申请人：——

  公开号：US8173645B2

  公开（公告）日：2012-05-08
• Design, synthesis and SAR of novel glucokinase activators
  作者：Zacharia S. Cheruvallath、Stephen L. Gwaltney、Mark Sabat、Mingnam Tang、Jun Feng、Haixia Wang、Joanne Miura、Prasuna Guntupalli、Andy Jennings、David Hosfield、Bumsup Lee、Yiqin Wu

  DOI：10.1016/j.bmcl.2013.01.093

  日期：2013.4

  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.