1,3-dihydro-2H-imidazo[4,5-c]quinoline-2-thione | 1254758-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,3-dihydro-2H-imidazo[4,5-c]quinoline-2-thione
• 英文别名: 1,3-Dihydroimidazo[4,5-c]quinoline-2-thione
• CAS: 1254758-42-3
• 化学式: C₁₀H₇N₃S
• 分子量: 201.252
• InChiKey: VYEYFLFZMMIODB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-2H-imidazo[4,5-c]quinoline-2-thione 、 5-(2-bromoacetyl)-2-chloro-benzenesulfonamide 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以92%的产率得到2-chloro-5-[(1H-imidazo[4,5-c]quinolin-2-ylsulfanyl)acetyl]benzenesulfonamide
  参考文献：
  名称：

  Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII

  摘要：

  A series of novel 2-chloro-5-[(1-benzimidazolyl- and 2-benzimidazolylsulfanyl) acetyl] benzene-sulfonamides were designed and synthesized. Their binding to recombinant human carbonic anhydrase (hCA)isozymes I, II, VII, and XIII was determined by isothermal titration calorimetry and thermal shift assay. The designed S-alkylated benzimidazole derivatives exhibited stronger binding than the indapamide-like N-alkylated benzimidazoles, with the K-d reaching about 50-100 nM with drug-targeted hCAs VII and XIII. The cocrystal structures of selected compounds with hCA II were determined by X-ray crystallography, and structural features of the binding event were revealed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.016
• 作为产物：
  描述：

  二硫化碳 、 3,4-二氨基喹啉 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以79%的产率得到1,3-dihydro-2H-imidazo[4,5-c]quinoline-2-thione
  参考文献：
  名称：

  Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII

  摘要：

  A series of novel 2-chloro-5-[(1-benzimidazolyl- and 2-benzimidazolylsulfanyl) acetyl] benzene-sulfonamides were designed and synthesized. Their binding to recombinant human carbonic anhydrase (hCA)isozymes I, II, VII, and XIII was determined by isothermal titration calorimetry and thermal shift assay. The designed S-alkylated benzimidazole derivatives exhibited stronger binding than the indapamide-like N-alkylated benzimidazoles, with the K-d reaching about 50-100 nM with drug-targeted hCAs VII and XIII. The cocrystal structures of selected compounds with hCA II were determined by X-ray crystallography, and structural features of the binding event were revealed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.016

文献信息

• SUBSTITUTED FUSED[1,2] IMIDAZO[4,5C] RING COMPOUNDS AND METHODS
  申请人：Kshirsagar Tushar A.

  公开号：US20090221551A1

  公开（公告）日：2009-09-03

  [1,2]Imidazo[4,5-c] ring compounds (e.g., imidazo[4,5-c]quinolines, imidazo[4,5-c]naphthyridines, and imidazo[4,5-c]pyridines) substituted with a fused ring containing an oxygen and/or nitrogen atom attached at the 1- and/or 2-position, pharmaceutical compositions containing the compounds, intermediates, methods of making the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  本发明涉及[1,2]咪唑[4,5-c]环化合物（例如，咪唑[4,5-c]喹啉，咪唑[4,5-c]萘啉和咪唑[4,5-c]吡啶），其取代了一个含氧和/或氮原子的融合环，并连接在1-和/或2-位，以及含有这些化合物的药物组合物，中间体，制备这些化合物的方法以及将这些化合物用作免疫调节剂的方法，用于诱导动物体内的细胞因子生物合成，并用于治疗病毒性和肿瘤性疾病。
• HYDROXY AND ALKOXY SUBSTITUTED 1H-IMIDAZOQUINOLINES AND METHODS
  申请人：Kshirsagar Tushar A.

  公开号：US20090221556A1

  公开（公告）日：2009-09-03

  1H-Imidazo[4,5-c]quinolin-4-amines with a hydroxy, alkoxy, hydroxyalkoxy, or alkoxyalkoxy substituent at the 2-position, pharmaceutical compositions containing these compounds, methods of making the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  本文介绍了在2位置具有羟基，烷氧基，羟基烷氧基或烷氧基烷氧基取代基的1H-咪唑并[4,5-c]喹啉-4-胺类化合物、含有这些化合物的制药组合物、制备这些化合物的方法、中间体以及这些化合物作为免疫调节剂的用途，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。
• US8088788B2
  申请人：——

  公开号：US8088788B2

  公开（公告）日：2012-01-03
• US8088790B2
  申请人：——

  公开号：US8088790B2

  公开（公告）日：2012-01-03
• US8377957B2
  申请人：——

  公开号：US8377957B2

  公开（公告）日：2013-02-19