N-(3-chlorobenzyl)indole-2-carboxylic acid | 220677-65-6

• 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: N-(3-chlorobenzyl)indole-2-carboxylic acid
• 英文别名: 1-[(3-chlorophenyl)methyl]indole-2-carboxylic acid
• CAS: 220677-65-6
• 化学式: C₁₆H₁₂ClNO₂
• 分子量: 285.73
• InChiKey: CVPGDWLGSKSTNB-UHFFFAOYSA-N

物化性质

• 沸点：
  520.3±35.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-chlorobenzyl)indole-2-carboxylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  [4 + 2]环化或丢失重排：铑催化发散合成具有抗癌活性的咔啉衍生物

  摘要：

  已经实现了一种不寻常的铑催化的 C–H 活化/Lossen 重排/oxa-Michael 加成串联环化以及众所周知的可调 C–H 活化/[4 + 2] 环化，从而导致区域-、化学-和非对映选择性获得多种五环α-咔啉和β-咔啉-1-酮衍生物，产率中等至良好，具有显着的抗癌活性。

  DOI：

  10.1021/acs.orglett.4c01050
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 在 乙醇 、 caesium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-(3-chlorobenzyl)indole-2-carboxylic acid
  参考文献：
  名称：

  [4 + 2]环化或丢失重排：铑催化发散合成具有抗癌活性的咔啉衍生物

  摘要：

  已经实现了一种不寻常的铑催化的 C–H 活化/Lossen 重排/oxa-Michael 加成串联环化以及众所周知的可调 C–H 活化/[4 + 2] 环化，从而导致区域-、化学-和非对映选择性获得多种五环α-咔啉和β-咔啉-1-酮衍生物，产率中等至良好，具有显着的抗癌活性。

  DOI：

  10.1021/acs.orglett.4c01050

文献信息

• New indole derivatives as factor Xa inhibitors
  申请人：——

  公开号：US20030199689A1

  公开（公告）日：2003-10-23

  The present invention relates to compounds of formula I, 1 in which R 0 ; R 1 ; R 2 ; R 3 ; R 4 ; R 5 ; R 6 ; R 7 ; Q; V, G and M have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is indicated. The invention furthermore relates to processes for the preparation of compounds of formula I, their use, in particular as pharmaceuticals for treating the foregoing conditions, and pharmaceutical preparations comprising them.

  本发明涉及具有式I的化合物，其中R0；R1；R2；R3；R4；R5；R6；R7；Q；V，G和M具有索赔中指示的含义。式I的化合物是有价值的药理活性化合物。它们表现出强烈的抗血栓作用，例如，适用于治疗和预防心血管疾病如血栓栓塞疾病或再狭窄。它们是血凝酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆抑制剂，通常可应用于存在因子Xa和/或因子VIIa不良活性的情况，或者在其治疗或预防需要抑制因子Xa和/或因子VIIa的情况下。此外，本发明还涉及制备式I化合物的方法，它们的用途，特别是作为用于治疗上述疾病的药物，以及包含它们的制剂。
• Monocyte chemoattractant protein-1 inhibitor compounds
  申请人：Zeneca Limited

  公开号：US06441004B1

  公开（公告）日：2002-08-27

  The invention concerns the use of a compound of the formula (I) in which Z, X, T, A, R1, R2, p and q have any of the meanings defined herein, and their pharmaceutically acceptable salts or in vivo hydrolysable esters, in the treatment of a disease or condition mediated by monocyte chemoattractant protein-1 (MCP-1). Certain of the components of formula (I) are novel and are provided, together with pharmaceutical compositions thereof, as further features of the invention.

  该发明涉及在治疗由单核细胞趋化蛋白-1（MCP-1）介导的疾病或症状中使用具有式（I）中Z、X、T、A、R1、R2、p和q中任意一个定义的含义的化合物，以及它们的药学上可接受的盐或体内可水解的酯。式（I）的某些组分是新颖的，并且随着药物组合物一起提供，作为该发明的进一步特征。
• NEW INDOLE DERIVATIVES AS FACTOR XA INHIBITORS
  申请人：NAZARE Mark

  公开号：US20090069565A1

  公开（公告）日：2009-03-12

  The present invention relates to compounds of formula I, in which R 0 ; R 1 ; R 2 ; R 3 ; R 4 ; R 5 ; R 6 ; R 7 ; Q; V, G and M have the meanings indicated in the claims. The compounds of formula I are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is indicated. The invention furthermore relates to processes for the preparation of compounds of formula I, their use, in particular as pharmaceuticals for treating the foregoing conditions, and pharmaceutical preparations comprising them.

  本发明涉及式I的化合物，其中R0; R1; R2; R3; R4; R5; R6; R7; Q; V，G和M具有声明中指示的含义。式I的化合物是有价值的药理活性化合物。它们表现出强烈的抗血栓作用，例如适用于治疗和预防心血管疾病，如血栓栓塞性疾病或再狭窄。它们是血凝酶酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆抑制剂，并且通常可以应用于存在因子Xa和/或因子VIIa不良活性的情况，或者治疗或预防需要抑制因子Xa和/或因子VIIa的情况。此外，本发明还涉及制备式I化合物的方法，它们的用途，特别是作为治疗上述疾病的药物以及包含它们的制药制剂。
• Indole-2-carboxamides as factor Xa inhibitors
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1314733A1

  公开（公告）日：2003-05-28

  The present invention relates to compounds of the formula I, in which R0 ; R1 ; R2 ; R3 ; R4 ; R5 ; R6 ; R7 ; Q; V, G and M have the meanings indicated in the claims. The compounds of the formula I are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable, for example, for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formula I, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them

  本发明涉及式 I 的化合物、 其中 R0 ; R1 ; R2 ; R3 ; R4 ; R5 ; R6 ; R7 ; Q; V, G 和 M 具有权利要求中所述的含义。式 I 的化合物是具有重要药理活性的化合物。它们具有很强的抗血栓作用，适用于治疗和预防血栓栓塞性疾病或再狭窄等心血管疾病。它们是血液凝固酶 Xa 因子 (FXa) 和/或 VIIa 因子 (FVIIa) 的可逆抑制剂，一般可用于 Xa 因子和/或 VIIa 因子存在不良活性的情况，或用于治疗或预防 Xa 因子和/或 VIIa 因子。本发明还涉及式 I 化合物的制备工艺、其用途（尤其是作为药物的活性成分）以及包含它们的药物制剂
• Factor Xa inhibitors based on a 2-carboxyindole scaffold: SAR of neutral P1 substituents
  作者：Marc Nazaré、Melanie Essrich、David W Will、Hans Matter、Kurt Ritter、Matthias Urmann、Armin Bauer、Herman Schreuder、Angela Dudda、Jörg Czech、Martin Lorenz、Volker Laux、Volkmar Wehner

  DOI：10.1016/j.bmcl.2004.06.020

  日期：2004.8

  A series of novel, highly potent 2-carboxyindole-based factor Xa inhibitors is described. Structural requirements for neutral ligands, which bind in the S1 pocket of factor Xa were investigated with the 2-carboxyindole scaffold. This privileged fragment assembly approach yielded a set of equipotent, selective inhibitors with structurally diverse neutral P1 substituents. (C) 2004 Elsevier Ltd. All rights reserved.