methyl 9-(3-methoxybenzyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylate

• 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: methyl 9-(3-methoxybenzyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylate
• 英文别名: Methyl 9-[(3-methoxyphenyl)methyl]-5,6,7,8-tetrahydrocarbazole-1-carboxylate
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: FONFJRPZTGLUKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 9-(3-methoxybenzyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylate 在 氢氧化钾 、 盐酸 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以64%的产率得到9-(3-methoxybenzyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid
  参考文献：
  名称：

  [EN] NOVEL INDOLE DERIVATES AS FABP-4 INHIBITORS
  [FR] NOUVEAUX DERIVES D'INDOLE UTILES COMME INHIBITEURS DE FABP-4

  摘要：

  本发明涉及新化合物（I），其中R0、R1、R2、R3、R4、R5、R6、R7、R8、A、B、n、X和Y如描述和权利要求中所定义；以及包含这些化合物的药物组合物，以及这些化合物在医学中的使用和用于制备作用于脂肪酸结合蛋白FABP-4的药物的方法。

  公开号：

  WO2004063156A1
• 作为产物：
  描述：

  Methyl 5,6,7,8-tetrahydrocarbazole-1-carboxylate 、 3-甲氧基氯苄 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 0.41h， 以55%的产率得到methyl 9-(3-methoxybenzyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylate
  参考文献：
  名称：

  [EN] NOVEL INDOLE DERIVATES AS FABP-4 INHIBITORS
  [FR] NOUVEAUX DERIVES D'INDOLE UTILES COMME INHIBITEURS DE FABP-4

  摘要：

  本发明涉及新化合物（I），其中R0、R1、R2、R3、R4、R5、R6、R7、R8、A、B、n、X和Y如描述和权利要求中所定义；以及包含这些化合物的药物组合物，以及这些化合物在医学中的使用和用于制备作用于脂肪酸结合蛋白FABP-4的药物的方法。

  公开号：

  WO2004063156A1

文献信息

• COMPOSITIONS AND METHODS FOR TREATING AND/OR PREVENTING CANCER BY INHIBITING FATTY ACID BINDING PROTEINS
  申请人：Lengyel Ernst

  公开号：US20120289570A1

  公开（公告）日：2012-11-15

  The present invention concerns methods and compositions for the inhibition or reduction of the primary tumor and metastasis by inhibition of fatty acid binding proteins.
• Compositions and Methods for Treating and/or Preventing Cancer by Inhibiting Fatty Acid Binding Proteins
  申请人：The University of Chicago

  公开号：US20140363522A1

  公开（公告）日：2014-12-11

  The present invention concerns methods and compositions for the inhibition or reduction of the primary tumor and metastasis by inhibition of fatty acid binding proteins.
• US8748470B2
  申请人：——

  公开号：US8748470B2

  公开（公告）日：2014-06-10
• [EN] NOVEL INDOLE DERIVATES AS FABP-4 INHIBITORS<br/>[FR] NOUVEAUX DERIVES D'INDOLE UTILES COMME INHIBITEURS DE FABP-4
  申请人：BIOVITRUM AB

  公开号：WO2004063156A1

  公开（公告）日：2004-07-29

  The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4. The present invention relates to novel compounds (I) wherein R0, R1, R2, R3, R4, R5, R6, R7, R8, A, B, n, X, and Y are as defined in the description and claims; and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament, which acts on the fatty acid binding protein FABP-4.

  本发明涉及新化合物（I），其中R0、R1、R2、R3、R4、R5、R6、R7、R8、A、B、n、X和Y如描述和权利要求中所定义；以及包含这些化合物的药物组合物，以及这些化合物在医学中的使用和用于制备作用于脂肪酸结合蛋白FABP-4的药物的方法。
• N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors
  作者：Tjeerd Barf、Fredrik Lehmann、Kristin Hammer、Saba Haile、Eva Axen、Carmen Medina、Jonas Uppenberg、Stefan Svensson、Lena Rondahl、Thomas Lundbäck

  DOI：10.1016/j.bmcl.2009.01.084

  日期：2009.3

  Small molecule inhibitors of adipocyte fatty-acid binding protein (A-FABP) have gained renewed interest following the recent publication of pharmacologically beneficial effects of such inhibitors. Despite the potential utility of selective A-FABP inhibitors within the fields of metabolic disease, inflammation and atherosclerosis, there are few examples of useful A-FABP inhibitors in the public domain. Herein, we describe the optimization of N-benzyl-tetrahydrocarbazole derivatives through the use of co-crystal structure guided medicinal chemistry efforts. This led to the identification of a potent and selective class of A-FABP inhibitors as illustrated by N-benzyl-hexahydrocyclohepta[b]indole 30.