3-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-propionic acid ethyl ester | 405275-43-6

• 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: 3-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-propionic acid ethyl ester
• 英文别名: ethyl 3-[1-[(4-chlorophenyl)methyl]indol-3-yl]propanoate
• CAS: 405275-43-6
• 化学式: C₂₀H₂₀ClNO₂
• 分子量: 341.837
• InChiKey: HJYLMVSQBJPGMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-propionic acid ethyl ester 在 乙醇 、 sodium hydroxide 作用下， 以 水 为溶剂， 以94%的产率得到3-<1-(4-chlorobenzyl)indol-3-yl>propionic acid
  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 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 3-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-propionic acid ethyl ester
  参考文献：
  名称：

  Synthetic N-pyridinyl(methyl)-indol-3-ylpropanamides as new potential immunosuppressive agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2006.12.013

文献信息

• 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.