ethyl 1-methyl-5-[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamido]-1H-indole-2-carboxylate | 481659-93-2

• 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: ethyl 1-methyl-5-[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamido]-1H-indole-2-carboxylate
• 英文别名: Ethyl 1-methyl-5-{[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carbonyl]amino}-1H-indole-2-carboxylate；ethyl 1-methyl-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indole-2-carboxylate
• CAS: 481659-93-2
• 化学式: C₂₆H₂₁F₃N₂O₃
• 分子量: 466.46
• InChiKey: LPGIJOKHQGNRDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-5-[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamido]-1H-indole-2-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以98%的产率得到1-Methyl-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indole-2-carboxylic acid
  参考文献：
  名称：

  In vitro and in vivo profile of 5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid benzylmethyl carbamoylamide (dirlotapide), a novel potent MTP inhibitor for obesity

  摘要：

  The synthesis of a novel gut selective MTP inhibitor, 5-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2carboxylic acid benzylmethyl carbamoylamide (dirlotapide), and its in vitro and in vivo profile are described. Dirlotapide (3) demonstrated excellent potency against MTP enzyme in HepG2 cells and canine hepatocytes. This novel MTP inhibitor also showed excellent efficacy when tested in a canine food intake model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.018
• 作为产物：
  描述：

  N-甲基-5-氨基吲哚-2-羧酸乙酯 、 4-三氟甲基-联苯-2-甲酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到ethyl 1-methyl-5-[4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxamido]-1H-indole-2-carboxylate
  参考文献：
  名称：

  In vitro and in vivo profile of 5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid benzylmethyl carbamoylamide (dirlotapide), a novel potent MTP inhibitor for obesity

  摘要：

  The synthesis of a novel gut selective MTP inhibitor, 5-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2carboxylic acid benzylmethyl carbamoylamide (dirlotapide), and its in vitro and in vivo profile are described. Dirlotapide (3) demonstrated excellent potency against MTP enzyme in HepG2 cells and canine hepatocytes. This novel MTP inhibitor also showed excellent efficacy when tested in a canine food intake model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.018

文献信息

• Triamide-substituted heterobicyclic compounds
  申请人：Pfizer Inc.

  公开号：US20030187053A1

  公开（公告）日：2003-10-02

  The invention relates to triamide MTP/ApoB inhibitors of the formula 1 1 wherein R 1 -R 8 are as defined in the specification, as well as pharmaceutical compositions and uses thereof, and processes for preparing the compounds. The compounds of the invention are useful for the treatment of obesity and lipid disorders.

  本发明涉及三酰胺MTP/ApoB抑制剂，其化学公式为1，其中R1-R8如说明书所述，以及包含这些化合物的药物组合物及其用途，以及制备这些化合物的方法。本发明的化合物可用于治疗肥胖和脂质紊乱。
• TRIAMIDE-SUBSTITUTED INDOLES, BENZOFURANES AND BENZOTHIOPHENES AS INHIBITORS OF MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN (MTP) AND/OR APOLIPOPROTEIN B (APO B) SECRETION
  申请人：Pfizer Products Inc.

  公开号：EP1404653A1

  公开（公告）日：2004-04-07
• US6720351B2
  申请人：——

  公开号：US6720351B2

  公开（公告）日：2004-04-13
• US6949572B2
  申请人：——

  公开号：US6949572B2

  公开（公告）日：2005-09-27
• US6979692B2
  申请人：——

  公开号：US6979692B2

  公开（公告）日：2005-12-27