(R)-3-(5-chloro-1H-indole-2-carboxamido)-4-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamido)butanoic acid | 1293409-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3-(5-chloro-1H-indole-2-carboxamido)-4-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamido)butanoic acid
• 英文别名: (3R)-3-[(5-chloro-1H-indole-2-carbonyl)amino]-4-[(5-methyl-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)amino]butanoic acid
• CAS: 1293409-34-3
• 化学式: C₂₁H₂₂ClN₅O₄S
• 分子量: 475.956
• InChiKey: MBXYCGUSMVLQGG-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (R)-3-(5-chloro-1H-indole-2-carboxamido)-4-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamido)butanoic acid
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132

文献信息

• Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors
  作者：Kenji Yoshikawa、Toshiharu Yoshino、Yoshihiro Yokomizo、Kouichi Uoto、Hiroyuki Naito、Katsuhiro Kawakami、Akiyoshi Mochizuki、Tsutomu Nagata、Makoto Suzuki、Hideyuki Kanno、Makoto Takemura、Toshiharu Ohta

  DOI：10.1016/j.bmcl.2011.01.132

  日期：2011.4

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.