3-aminomethyl-1-oxo-2,3,4,9-tetrahydro-1H-β-carboline-6-carboxylic acid thiazol-2-yl amide | 916522-31-1

• 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: 3-aminomethyl-1-oxo-2,3,4,9-tetrahydro-1H-β-carboline-6-carboxylic acid thiazol-2-yl amide
• 英文别名: Indole-based 6-membered lactam, 3b；3-(aminomethyl)-1-oxo-N-(1,3-thiazol-2-yl)-2,3,4,9-tetrahydropyrido[3,4-b]indole-6-carboxamide
• CAS: 916522-31-1
• 化学式: C₁₆H₁₅N₅O₂S
• 分子量: 341.393
• InChiKey: FMRWLLNOPBTLDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(azidomethyl)-1-oxo-N-(thiazol-2-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-6-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 以65%的产率得到3-aminomethyl-1-oxo-2,3,4,9-tetrahydro-1H-β-carboline-6-carboxylic acid thiazol-2-yl amide
  参考文献：
  名称：

  Synthesis and SAR studies of indole-based MK2 inhibitors

  摘要：

  Chemistry has been developed to specifically functionalize two structurally similar classes of indole-based MK2 inhibitors at positions prompted by a combination of X-ray crystallographic and computer assisted drug design. A gain in molecular potency was obtained by introducing aminomethyl groups to the lactam rings of 6-arylcarbamoyl-tetrahydro-beta-carbolinone and 6-arylcarbamoyl-dihydropyrazino[1,2-a] indolone MK2 inhibitors. In addition, improvements in molecular potency were achieved by expansion of the lactam from a 6- to 7-membered ring leading to 7-arylcarbamoyl-tetrahydro-[1,4] diazepino[1,2-a]indolones. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.119

文献信息

• Anti-Cytokine Heterocyclic Compounds
  申请人：Goldberg Daniel

  公开号：US20060276496A1

  公开（公告）日：2006-12-07

  Heterocyclic compounds and analogues thereof and their use as inhibitors of Mitogen-Activated Protein Kinase-Activated Protein kinase-2 (MAPKAP-k2), and also to a method for preventing or treating a disease or disorder that can be treated or prevented by modulating the activity of MAPKAP-K2 in a subject and to pharmaceutical compositions and kits that include these MAPKAP-K2 inhibitors.

  杂环化合物及其类似物以及它们作为丝裂原活化蛋白激酶-2（MAPKAP-k2）抑制剂的用途，以及用于预防或治疗可以通过调节受试者中MAPKAP-K2活性来治疗或预防的疾病或紊乱的方法，以及包括这些MAPKAP-K2抑制剂的药物组合物和试剂盒。
• Synthesis and SAR studies of indole-based MK2 inhibitors
  作者：Zhaoming Xiong、Donghong Amy Gao、Derek A. Cogan、Daniel R. Goldberg、Ming-Hong Hao、Neil Moss、Edward Pack、Chris Pargellis、Donna Skow、Thomas Trieselmann、Brian Werneburg、Andre White

  DOI：10.1016/j.bmcl.2008.01.119

  日期：2008.3

  Chemistry has been developed to specifically functionalize two structurally similar classes of indole-based MK2 inhibitors at positions prompted by a combination of X-ray crystallographic and computer assisted drug design. A gain in molecular potency was obtained by introducing aminomethyl groups to the lactam rings of 6-arylcarbamoyl-tetrahydro-beta-carbolinone and 6-arylcarbamoyl-dihydropyrazino[1,2-a] indolone MK2 inhibitors. In addition, improvements in molecular potency were achieved by expansion of the lactam from a 6- to 7-membered ring leading to 7-arylcarbamoyl-tetrahydro-[1,4] diazepino[1,2-a]indolones. (C) 2008 Elsevier Ltd. All rights reserved.