2-piperidin-4-yl-thiazole-4-carboxylic acid (5,6-dimethyl-1H-benzoimidazol-2-yl)-amide | 881196-95-8

• 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: 2-piperidin-4-yl-thiazole-4-carboxylic acid (5,6-dimethyl-1H-benzoimidazol-2-yl)-amide
• 英文别名: N-(5,6-dimethyl-1H-benzimidazol-2-yl)-2-piperidin-4-yl-1,3-thiazole-4-carboxamide
• CAS: 881196-95-8
• 化学式: C₁₈H₂₁N₅OS
• 分子量: 355.464
• InChiKey: OOFCKWZAXSLIKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-piperidin-4-yl-thiazole-4-carboxylic acid (5,6-dimethyl-1H-benzoimidazol-2-yl)-amide 、 4-氯噻吩并[3,2-d]嘧啶 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(5,6-dimethyl-1H-benzimidazol-2-yl)-2-(1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl)-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  A novel class of potent NF-κB signaling inhibitors

  摘要：

  A novel class of NF-kappa B pathway signaling inhibitors was discovered by virtual screening, medicinal chemistry, and QSAR analysis. An initial set of compounds inhibited NF-kappa B signaling in a whole cell reporter gene assay in the micro-molar range. Activity was improved step by step by medicinal chemistry to yield nano-molar signaling inhibitors. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.08.022
• 作为产物：
  描述：

  tert-butyl 4-[4-[(5,6-dimethyl-1H-benzimidazol-2-yl)carbamoyl]-1,3-thiazol-2-yl]piperidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-piperidin-4-yl-thiazole-4-carboxylic acid (5,6-dimethyl-1H-benzoimidazol-2-yl)-amide
  参考文献：
  名称：

  A novel class of potent NF-κB signaling inhibitors

  摘要：

  A novel class of NF-kappa B pathway signaling inhibitors was discovered by virtual screening, medicinal chemistry, and QSAR analysis. An initial set of compounds inhibited NF-kappa B signaling in a whole cell reporter gene assay in the micro-molar range. Activity was improved step by step by medicinal chemistry to yield nano-molar signaling inhibitors. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.08.022

文献信息

• NOVEL PIPERIDIN-4-YL-THIAZOLE-CARBOXAMIDE ANALOGUES AS INHIBITORS OF T-CELL PROLIFERATION AND USES THEREOF
  申请人：4SC AG

  公开号：EP2343293A1

  公开（公告）日：2011-07-13

  The present invention relates to compounds of the general formula (I) and salts thereof, wherein R1 is independently hydrogen, alkyl, cycloalkyl, hydroxyalkyl, haloalkyl, haloalkyloxy, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl or substituted arylalkyl; R2 is independently R3 is independently alkyl, cycloalkyl, alkoxy, alkylamine, -OH, -SH, alkylthio, hydroxyalkyl, haloalkyl, haloalkyloxy, aryl or heteroaryl, R4 is independently alkyl, cycloalkyl, alkoxy, alkylamine, alkylthio, hydroxyalkyl, haloalkyl, haloalkyloxy, aryl or heteroaryl; R5 is independently H, COR6, CO2R6, SOR6, SO2R6, SO3R6, alkyl, cycloalkyl, alkoxy, -NH2, alkylamine, -NR7COR6, halogen, -OH, -SH, alkylthio, hydroxyalkyl, haloalkyl, haloalkyloxy, aryl or heteroaryl; R6 is independently H, alkyl, cycloalkyl, -NH2, alkylamine, aryl or heteroaryl; R7 is independently H, alkyl, cycloalkyl, alkoxy, -OH, -SH, alkylthio, hydroxyalkyl, aryl, or heteroaryl; p is 0, or 1; q is 0, or 1; X is CO, or SO2.

  本发明涉及通式 (I) 的化合物 及其盐类，其中 R1 独立地是氢、烷基、环烷基、羟烷基、卤代烷基、卤代烷氧基、芳基、取代芳基、杂芳基、取代杂芳基、芳烷基或取代芳烷基； R2 独立地 R3 独立地为烷基、环烷基、烷氧基、烷基胺、-OH、-SH、烷硫基、羟基烷基、卤代烷基、卤代烷氧基、芳基或杂芳基、 R4 独立地是烷基、环烷基、烷氧基、烷基胺、烷硫基、羟基烷基、卤代烷基、卤代烷氧基、芳基或杂芳基； R5 独立地为 H、COR6、CO2R6、SOR6、SO2R6、SO3R6、烷基、环烷基、烷氧基、-NH2、烷基胺、-NR7COR6、卤素、-OH、-SH、烷硫基、羟基烷基、卤代烷基、卤代烷氧基、芳基或杂芳基； R6 独立地为 H、烷基、环烷基、-NH2、烷基胺、芳基或杂芳基； R7 独立地为 H、烷基、环烷基、烷氧基、-OH、-SH、烷硫基、羟基烷基、芳基或杂芳基； p 为 0 或 1 q 为 0 或 1； X 是 CO 或 SO2。
• A novel class of potent NF-κB signaling inhibitors
  作者：Johann Leban、Marcel Baierl、Jan Mies、Viola Trentinaglia、Sandra Rath、Kerstin Kronthaler、Kristina Wolf、Astrid Gotschlich、Markus H.J. Seifert

  DOI：10.1016/j.bmcl.2007.08.022

  日期：2007.11

  A novel class of NF-kappa B pathway signaling inhibitors was discovered by virtual screening, medicinal chemistry, and QSAR analysis. An initial set of compounds inhibited NF-kappa B signaling in a whole cell reporter gene assay in the micro-molar range. Activity was improved step by step by medicinal chemistry to yield nano-molar signaling inhibitors. (c) 2007 Published by Elsevier Ltd.