1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinylimidazole-4-carboxylic acid | 871314-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinylimidazole-4-carboxylic acid
• CAS: 871314-92-0
• 化学式: C₁₇H₁₁Cl₃N₂O₃S
• 分子量: 429.711
• InChiKey: CZLDWFMAPLKFAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinylimidazole-4-carboxylic acid 、 1-氨基哌啶 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-5-methanesulfinyl-1H-imidazole-4-carboxylic acid piperidin-1-ylamide
  参考文献：
  名称：

  Probing the cannabinoid CB1/CB2 receptor subtype selectivity limits of 1,2-diarylimidazole-4-carboxamides by fine-tuning their 5-substitution pattern

  摘要：

  The cannabinoid CB1/CB2 receptor subtype selectivity in the 1,2-diarylimidazole-4-carboxamide series was boosted by fine-tuning its 5-substitution pattern. The presence of the 5-methylsulfonyl group in 11 led to a greater than similar to 840-fold CB1/CB2 subtype selectivity. The compounds 10, 18 and 19 were found more active than rimonabant (1) in a CB1-mediated rodent hypotension model after oral administration. Our findings suggest a limited brain exposure of the P-glycoprotein substrates 11, 12 and 21. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.068
• 作为产物：
  描述：

  Tert-butyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinylimidazole-4-carboxylate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfinylimidazole-4-carboxylic acid
  参考文献：
  名称：

  Probing the cannabinoid CB1/CB2 receptor subtype selectivity limits of 1,2-diarylimidazole-4-carboxamides by fine-tuning their 5-substitution pattern

  摘要：

  The cannabinoid CB1/CB2 receptor subtype selectivity in the 1,2-diarylimidazole-4-carboxamide series was boosted by fine-tuning its 5-substitution pattern. The presence of the 5-methylsulfonyl group in 11 led to a greater than similar to 840-fold CB1/CB2 subtype selectivity. The compounds 10, 18 and 19 were found more active than rimonabant (1) in a CB1-mediated rodent hypotension model after oral administration. Our findings suggest a limited brain exposure of the P-glycoprotein substrates 11, 12 and 21. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.068

文献信息

• TETRASUBSTITUTED IMIDAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR MODULATORS WITH A HIGH CB1/CB2 RECEPTOR SUBTYPE SELECTIVITY
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1756066A1

  公开（公告）日：2007-02-28
• [EN] TETRASUBSTITUTED IMIDAZOLE DERIVATIVES AS CANNABINOID CB1 RECEPTOR MODULATORS WITH A HIGH CB1/CB2 RECEPTOR SUBTYPE SELECTIVITY<br/>[FR] DERIVES D'IMIDAZOLE TETRASUBSTITUES UTILISES COMME MODULATEURS DU RECEPTEUR DES CANNABINOIDES CB1 A ACTIVITE DE SELECTIVITE DE SOUS-TYPES DU RECEPTEUR CB1/CB2 ELEVEE
  申请人：SOLVAY PHARM BV

  公开号：WO2005118553A1

  公开（公告）日：2005-12-15

  The present invention relates to 1,2,4,5-tetrasubstituted imidazole derivatives as selective cannabinoid CB1 receptor modulators, in particular CB1 receptor antagonists or inverse agonists having a high CB1/CB2 receptor subtype selectivity, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said imidazole derivatives. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. A beneficial effect is disclosed herein or apparent to a person skilled in the art from the specification and general knowledge in the art. The invention also relates to the use of a compound of the invention for the manufacture of a medicament for treating or preventing a disease or condition. More particularly, the invention relates to a new use for the treatment of a disease or condition disclosed herein or apparent to a person skilled in the art from the specification and general knowledge in the art. In embodiments of the invention specific compounds disclosed herein are used for the manufacture of a medicament useful in the treatment of psychiatric and neurological disorders. The compounds have the general formula (I) wherein the symbols have the meanings given in the specification.
• Probing the cannabinoid CB1/CB2 receptor subtype selectivity limits of 1,2-diarylimidazole-4-carboxamides by fine-tuning their 5-substitution pattern
  作者：Jos H.M. Lange、Martina A.W. van der Neut、Alice J.M. Borst、Mahmut Yildirim、Herman H. van Stuivenberg、Bernard J. van Vliet、Chris G. Kruse

  DOI：10.1016/j.bmcl.2010.03.068

  日期：2010.5

  The cannabinoid CB1/CB2 receptor subtype selectivity in the 1,2-diarylimidazole-4-carboxamide series was boosted by fine-tuning its 5-substitution pattern. The presence of the 5-methylsulfonyl group in 11 led to a greater than similar to 840-fold CB1/CB2 subtype selectivity. The compounds 10, 18 and 19 were found more active than rimonabant (1) in a CB1-mediated rodent hypotension model after oral administration. Our findings suggest a limited brain exposure of the P-glycoprotein substrates 11, 12 and 21. (C) 2010 Elsevier Ltd. All rights reserved.