3-[5-Chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-propionic acid | 850895-38-4

• 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-[5-Chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-propionic acid
• CAS: 850895-38-4
• 化学式: C₁₈H₁₅Cl₂NO₂
• 分子量: 348.229
• InChiKey: GWSFOOYCMICQHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-甲氨基吡啶 、 3-[5-Chloro-1-(4-chloro-benzyl)-1H-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， 反应 12.0h， 以75%的产率得到N-[(pyridin-4-yl)methyl]-3-[5-chloro-1-(4-chlorobenzyl)indol-3-yl]propanamide
  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
• 作为产物：
  描述：

  ethyl (E) 3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propenoate 在 镍 sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 3-[5-Chloro-1-(4-chloro-benzyl)-1H-indol-3-yl]-propionic acid
  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.