N-(2-{[(5-chlorothiophene-2-carbonyl)amino]methyl}-5-[(2-cyanoethyl)carbamoyl]phenyl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide | 1057649-97-4

• 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: N-(2-{[(5-chlorothiophene-2-carbonyl)amino]methyl}-5-[(2-cyanoethyl)carbamoyl]phenyl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide
• 英文别名: N-[2-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-5-(2-cyanoethylcarbamoyl)phenyl]-5-methyl-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carboxamide
• CAS: 1057649-97-4
• 化学式: C₂₄H₂₃ClN₆O₃S₂
• 分子量: 543.07
• InChiKey: PEVJTGQDNHMIBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  184
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(2-{[(5-chlorothiophene-2-carbonyl)amino]methyl}-5-[(2-cyanoethyl)carbamoyl]phenyl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide 在 叠氮基三甲基硅烷 、 水 、 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 192.0h， 生成 N-[2-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-5-(2H-tetrazol-5-yl)phenyl]-5-methyl-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carboxamide
  参考文献：
  名称：

  Orally active zwitterionic factor Xa inhibitors with long duration of action

  摘要：

  We have optimized 2-aminomethylphenylamine derivative as a factor Xa inhibitor. Several polar functional groups were introduced in the central phenyl ring, and we focused on zwitter ionic compound showing continuous inhibitory activity in oral administration test. In vitro and oral activities were improved by optimization of S1 and S4 ligands. Incorporating the interaction with S1-beta pocket enhanced in vitro factor Xa inhibitory activity to less than 1 nM. Many zwitter ionic compounds showed long duration of action and potent inhibitory activity and high AUC values in oral administration tests to monkeys. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.021
• 作为产物：
  描述：

  3-氨基丙腈 、 4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-3-[(5-methyl-6,7-dihydro-4H-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)amino]benzoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以68%的产率得到N-(2-{[(5-chlorothiophene-2-carbonyl)amino]methyl}-5-[(2-cyanoethyl)carbamoyl]phenyl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide
  参考文献：
  名称：

  Orally active zwitterionic factor Xa inhibitors with long duration of action

  摘要：

  We have optimized 2-aminomethylphenylamine derivative as a factor Xa inhibitor. Several polar functional groups were introduced in the central phenyl ring, and we focused on zwitter ionic compound showing continuous inhibitory activity in oral administration test. In vitro and oral activities were improved by optimization of S1 and S4 ligands. Incorporating the interaction with S1-beta pocket enhanced in vitro factor Xa inhibitory activity to less than 1 nM. Many zwitter ionic compounds showed long duration of action and potent inhibitory activity and high AUC values in oral administration tests to monkeys. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.021