6-chloro-N-(3-oxo-2,3-dihydro-1H-inden-5-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide | 1190482-04-2

• 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-(3-oxo-2,3-dihydro-1H-inden-5-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide
• 英文别名: 6-chloroimidazo [2,1-b]thiazole-5-sulfonic acid(3-oxo-indan-5-yl)-amide；6-chloro-N-(3-oxo-1,2-dihydroinden-5-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide
• CAS: 1190482-04-2
• 化学式: C₁₄H₁₀ClN₃O₃S₂
• 分子量: 367.837
• InChiKey: AUNAYRTVQNWDGJ-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-(3-oxo-2,3-dihydro-1H-inden-5-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide 、 氨基胍碳酸氢盐 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以59%的产率得到2-(6-{[(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：

  6-氨基-1-茚酮 、 6-氯咪唑[2,1-b][1,3]噻唑-5-磺酰氯 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 16.25h， 以75%的产率得到6-chloro-N-(3-oxo-2,3-dihydro-1H-inden-5-yl)imidazo[2,1-b][1,3]thiazole-5-sulfonamide
  参考文献：
  名称：

  Substituted N-imidazo(2, 1-b) thiazole-5-sulfonamide derivatives as 5-TH6 ligands

  摘要：

  该发明涉及具有对5-HT6受体具有药理活性的化合物(I)，更具体地涉及一些N-咪唑[2,1-b]噻唑酮-5-磺酰胺衍生物，以及制备这些化合物的方法，包括含有它们的药物组合物，以及它们用于治疗和/或预防涉及5-HT6的疾病。

  公开号：

  EP2116547A1

文献信息

• Substituted N-imidazo(2, 1-b) thiazole-5-sulfonamide derivatives as 5-TH6 ligands
  申请人：Laboratorios Del. Dr. Esteve, S.A.

  公开号：EP2116547A1

  公开（公告）日：2009-11-11

  The invention relates to compounds (I) having pharmacological activity towards the 5-HT6 receptor, and more particularly to some N-imidazo[2,1-b]thiazole-5-sulfonamide derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT6 is involved.

  该发明涉及具有对5-HT6受体具有药理活性的化合物(I)，更具体地涉及一些N-咪唑[2,1-b]噻唑酮-5-磺酰胺衍生物，以及制备这些化合物的方法，包括含有它们的药物组合物，以及它们用于治疗和/或预防涉及5-HT6的疾病。
• SUBSTITUTED N-IMIDAZO[2,1-B]THIAZOLE-5-SULFONAMIDE DERIVATIVES AS 5-HT6 LIGANDS
  申请人：Mas Prio Josep

  公开号：US20110105555A1

  公开（公告）日：2011-05-05

  The invention relates to compounds having pharmacological activity towards the 5-HT 6 receptor, and more particularly to some N-imidazo[2,1-b]thiazole-5-sulfonamide derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use for the treatment and or prophylaxis of a disease in which 5-HT 6 is involved.

  本发明涉及具有对5-HT6受体药理活性的化合物，更具体地涉及一些N-咪唑[2,1-b]噻唑-5-磺酰胺衍生物，制备这些化合物的过程，包含它们的制药组合物，以及它们用于治疗和/或预防5-HT6参与的疾病的用途。
• 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%).