3-<1-(4-chlorobenzyl)indol-3-yl>propionic acid | 219544-54-4

• 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-<1-(4-chlorobenzyl)indol-3-yl>propionic acid
• 英文别名: 3-{1-[(4-chlorophenyl)methyl]-1H-indol-3-yl}propanoic acid；3-[1-[(4-chlorophenyl)methyl]indol-3-yl]propanoic acid
• CAS: 219544-54-4
• 化学式: C₁₈H₁₆ClNO₂
• mdl: MFCD16990629
• 分子量: 313.784
• InChiKey: FIAKLGDVKKJABU-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C (decomp)
• 沸点：
  530.5±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 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：

  6-氨基喹啉 、 3-<1-(4-chlorobenzyl)indol-3-yl>propionic acid 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-[1-[(4-chlorophenyl)methyl]indol-3-yl]-N-quinolin-6-ylpropanamide
  参考文献：
  名称：

  Synthesis of N-aryl-3-(indol-3-yl)propanamides and their immunosuppressive activities

  摘要：

  N-Aryl-3-(indol-3-yl)propanamides were synthesized and their immunosuppressive activities were evaluated. This study highlighted the promising potency of 3-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-(4-nitrophenyl) propanamide 15 which exhibited a significant inhibitory activity on murine splenocytes proliferation assay in vitro and on mice delayed-type hypersensitivity (DTH) assay in vivo. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.001
• 作为产物：
  描述：

  3-吲哚丙酸 在 盐酸 、 sodium hydroxide 、 caesium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 3-<1-(4-chlorobenzyl)indol-3-yl>propionic acid
  参考文献：
  名称：

  New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors

  摘要：

  The authors have described the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.07.057

文献信息

• (1-Benzylindole-3-yl)alkanoic Acids; Novel Nonsteroidal Inhibitors of Steroid 5.ALPHA.-Reductase (I).
  作者：Kozo SAWADA、Hideo HIRAI、Patrick GOLDEN、Satoshi OKADA、Yuki SAWADA、Masashi HASHIMOTO、Hirokazu TANAKA

  DOI：10.1248/cpb.46.1683

  日期：——

  A novel series of indole-3-alkanoic acids with varied N-benzyl substituents were synthesized as nonsteroidal inhibitors of steroid 5 alpha-reductase. The structure-activity relationships in this series were studied and the optimum carboxylic acid side chain was butyric acid. Furthermore, compounds with a diaryl substituent at the 1-position of the indole ring displayed strong inhibitory activities

  合成了一系列具有变化的N-苄基取代基的新型吲哚-3-链烷酸作为甾体5α-还原酶的非甾体抑制剂。研究了该系列中的构效关系，最佳羧酸侧链为丁酸。此外，在吲哚环的1-位具有二芳基取代基的化合物在体外显示出强的抑制活性。在这些衍生物中，4- [1-（6,6-二甲基-6H-二苯并[b，d]吡喃-3-基）甲基吲哚-3-基]丁二酸（FR119680）在体外具有很高的抑制活性。在rat割的年轻大鼠模型中具有抗大鼠前列腺5α-还原酶（IC50 = 5.0 nM）的良好体内活性。
• Synthetic N-pyridinyl(methyl)-indol-3-ylpropanamides as new potential immunosuppressive agents
  作者：Delphine Carbonnelle、Morgane Lardic、Alexandra Dassonville、Elise Verron、Jean-Yves Petit、Muriel Duflos、François Lang

  DOI：10.1016/j.ejmech.2006.12.013

  日期：2007.5

  Several N-pyridinyl(methyl)-indol-3-ylpropanamides were synthesized and pharmacological evaluations of their immumosuppressive potential were performed. Among thirteen compounds tested in vitro on murine T proliferation, three showed interesting inhibiting activity. For the most active compound (propanamide 18), immunosuppressive activity was documented both in vitro on human T lymphocytes proliferation and in vivo on mice delayed-type hypersensitivity. These experimental data demonstrated that these compounds hold potential as immunosuppressive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.
• New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors
  作者：Alexandra Dassonville、Anne Bretéché、Johan Evano、Muriel Duflos、Guillaume le Baut、Nicole Grimaud、Jean-Yves Petit

  DOI：10.1016/j.bmcl.2004.07.057

  日期：2004.11

  The authors have described the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. (C) 2004 Published by Elsevier Ltd.
• Synthesis of N-aryl-3-(indol-3-yl)propanamides and their immunosuppressive activities
  作者：Francis Giraud、Pascal Marchand、Delphine Carbonnelle、Michael Sartor、François Lang、Muriel Duflos

  DOI：10.1016/j.bmcl.2010.07.001

  日期：2010.9

  N-Aryl-3-(indol-3-yl)propanamides were synthesized and their immunosuppressive activities were evaluated. This study highlighted the promising potency of 3-[1-(4-chlorobenzyl)-1H-indol-3-yl]-N-(4-nitrophenyl) propanamide 15 which exhibited a significant inhibitory activity on murine splenocytes proliferation assay in vitro and on mice delayed-type hypersensitivity (DTH) assay in vivo. (C) 2010 Elsevier Ltd. All rights reserved.