tert-butyl 3-(((1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-yl)thio)methyl)azetidine-1-carboxylate | 1236007-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: tert-butyl 3-(((1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-yl)thio)methyl)azetidine-1-carboxylate
• CAS: 1236007-20-7
• 化学式: C₂₅H₃₇N₃O₂S
• 分子量: 443.654
• InChiKey: UTWLAUCNRWCXEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  47.36
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(((1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-yl)thio)methyl)azetidine-1-carboxylate 在 sodium tungstate 、 三甲基氯硅烷 、 双氧水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-((1-(cyclopropylmethyl)-2-neopentyl-1H-benzoimidazol-5-ylsulfonyl)methyl)azetidine-1-carboxamide
  参考文献：
  名称：

  Identification of a highly potent and selective CB2 agonist, RQ-00202730, for the treatment of irritable bowel syndrome

  摘要：

  Herein we report the identification of a highly potent and selective CB2 agonist, RQ-00202730 (40), obtained by lead optimization of the benzimidazole scaffold. Compound 40 showed strong agonistic activity with an EC50 of 19 nM and excellent selectivity (>1300-fold) over the CB1 receptor. Compound 40 displayed a dose dependent analgesic effect on TNBS-induced visceral hypersensitivity in rats by oral administration (ED50 0.66 mg/kg at 2.5 h after oral administration). In addition, 40 did not show a significant effect on body temperature in rats after oral administration at 300 mg/kg. These findings suggest that highly selective CB2 agonists will be effective agents for IBS therapy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.062
• 作为产物：
  描述：

  4-溴-1-氟-2-硝基苯 在 盐酸 、 tris-(dibenzylideneacetone)dipalladium(0) 、 铁粉 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 tert-butyl 3-(((1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-yl)thio)methyl)azetidine-1-carboxylate
  参考文献：
  名称：

  Identification of a highly potent and selective CB2 agonist, RQ-00202730, for the treatment of irritable bowel syndrome

  摘要：

  Herein we report the identification of a highly potent and selective CB2 agonist, RQ-00202730 (40), obtained by lead optimization of the benzimidazole scaffold. Compound 40 showed strong agonistic activity with an EC50 of 19 nM and excellent selectivity (>1300-fold) over the CB1 receptor. Compound 40 displayed a dose dependent analgesic effect on TNBS-induced visceral hypersensitivity in rats by oral administration (ED50 0.66 mg/kg at 2.5 h after oral administration). In addition, 40 did not show a significant effect on body temperature in rats after oral administration at 300 mg/kg. These findings suggest that highly selective CB2 agonists will be effective agents for IBS therapy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.062

文献信息

• [EN] N-SUBSTITUTED SATURATED HETEROCYCLIC SULFONE COMPOUNDS WITH CB2 RECEPTOR AGONISTIC ACTIVITY<br/>[FR] COMPOSÉS DE SULFONE HÉTÉROCYCLIQUES SATURÉS N-SUBSTITUÉS AYANT UNE ACTIVITÉ AGONISTE DU RÉCEPTEUR CB2
  申请人：RAQUALIA PHARMA INC

  公开号：WO2010084767A1

  公开（公告）日：2010-07-29

  This invention relates to compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein X, R1, R2,R3, R4, R5, R6, R7, k, m, n, p, q, r and s are each as described herein, and compositions containing such compounds, and the use of such compounds in the treatment of a condition mediated by CB2 receptor activity.

  这项发明涉及式(I)的化合物或其药用盐，其中X、R1、R2、R3、R4、R5、R6、R7、k、m、n、p、q、r和s如本文所述，并含有这种化合物的组合物，以及利用这种化合物治疗由CB2受体活性介导的疾病的用途。