6-chloro-N-(1-oxo-2,3-dihydro-1H-inden-4-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide | 1190482-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-chloro-N-(1-oxo-2,3-dihydro-1H-inden-4-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide
• 英文别名: 6-chloro-N-(1-oxo-2,3-dihydroinden-4-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide
• CAS: 1190482-07-5
• 化学式: C₁₄H₁₀ClN₃O₃S₂
• 分子量: 367.837
• InChiKey: AXUHTKJPYFMEOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-chloro-N-(1-oxo-2,3-dihydro-1H-inden-4-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide 、 氨基胍碳酸氢盐 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以66%的产率得到2-(4-{[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-1-ylidene)hydrazinecarboximidamide hydrochloride
  参考文献：
  名称：

  Identification of Novel Indanylsulfonamide Guanylhydrazones as Potent 5-HT₆ Serotonin Receptor Antagonists

  摘要：

  Changing the N,N-(dimethylamino)ethyl side chain in the N-[3-(aminoethyl)inden-5-yl]sulfonamide 5-HT6 serotonin receptor agonists 1 by a conformationally rigid guanylhydrazone moiety at the indene 3-position led to the identification of the title indanylguanylhydrazones 6, which exhibited excellent binding affinities and an antagonistic response at the 5-HT6 receptor, with K-i and IC50 values in the nanomolar range (K-i >= 1.2 nM, IC50 >= 47 nM, and I-max <= 173%).

  DOI：

  10.1021/jm900796p
• 作为产物：
  描述：

  4-氨基茚酮 、 6-氯咪唑[2,1-b][1,3]噻唑-5-磺酰氯 以 吡啶 为溶剂， 以45%的产率得到6-chloro-N-(1-oxo-2,3-dihydro-1H-inden-4-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide
  参考文献：
  名称：

  Identification of Novel Indanylsulfonamide Guanylhydrazones as Potent 5-HT₆ Serotonin Receptor Antagonists

  摘要：

  Changing the N,N-(dimethylamino)ethyl side chain in the N-[3-(aminoethyl)inden-5-yl]sulfonamide 5-HT6 serotonin receptor agonists 1 by a conformationally rigid guanylhydrazone moiety at the indene 3-position led to the identification of the title indanylguanylhydrazones 6, which exhibited excellent binding affinities and an antagonistic response at the 5-HT6 receptor, with K-i and IC50 values in the nanomolar range (K-i >= 1.2 nM, IC50 >= 47 nM, and I-max <= 173%).

  DOI：

  10.1021/jm900796p

文献信息

• Identification of Novel Indanylsulfonamide Guanylhydrazones as Potent 5-HT₆ Serotonin Receptor Antagonists
  作者：Neus Mesquida、Sara López-Pérez、Immaculada Dinarès、Jordi Frigola、Ramon Mercè、Jörg Holenz、Raquel Pérez、Javier Burgueño、Ermitas Alcalde

  DOI：10.1021/jm900796p

  日期：2009.10.8

  Changing the N,N-(dimethylamino)ethyl side chain in the N-[3-(aminoethyl)inden-5-yl]sulfonamide 5-HT6 serotonin receptor agonists 1 by a conformationally rigid guanylhydrazone moiety at the indene 3-position led to the identification of the title indanylguanylhydrazones 6, which exhibited excellent binding affinities and an antagonistic response at the 5-HT6 receptor, with K-i and IC50 values in the nanomolar range (K-i >= 1.2 nM, IC50 >= 47 nM, and I-max <= 173%).