2-[(5-chloro-1,3-benzothiazol-2-yl)thio]hexanoic acid | 1331734-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]hexanoic acid
• CAS: 1331734-04-3
• 化学式: C₁₃H₁₄ClNO₂S₂
• 分子量: 315.845
• InChiKey: BJPDPHPGBSECHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯磺酰胺 、 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]hexanoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]-N-(phenylsulfonyl)hexanamide
  参考文献：
  名称：

  Benzothiazole-based N-(phenylsulfonyl)amides as a novel family of PPARα antagonists

  摘要：

  The discovery of PPAR antagonists is emerging as an useful tool for elucidating the biological role of the receptor. Here we report the identification of N-(phenylsulfonyl)amides containing the benzothiazole scaffold, a novel class of potent PPAR alpha antagonists obtained from chemical modification of carboxylic acid agonists. In this work, a group of phenylsulfonamides were synthesized and in vitro evaluated against the agonistic effect of GW7647; they showed an inhibitory effect on PPARa activation, with best compounds revealing a dose-dependent antagonistic profile. Some of these antagonists showed also an inhibitory effect on CPT1A pattern expression. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.028
• 作为产物：
  描述：

  ethyl 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]hexanoate 在 乙醇 、 sodium hydroxide 作用下， 以63%的产率得到2-[(5-chloro-1,3-benzothiazol-2-yl)thio]hexanoic acid
  参考文献：
  名称：

  Benzothiazole-based N-(phenylsulfonyl)amides as a novel family of PPARα antagonists

  摘要：

  The discovery of PPAR antagonists is emerging as an useful tool for elucidating the biological role of the receptor. Here we report the identification of N-(phenylsulfonyl)amides containing the benzothiazole scaffold, a novel class of potent PPAR alpha antagonists obtained from chemical modification of carboxylic acid agonists. In this work, a group of phenylsulfonamides were synthesized and in vitro evaluated against the agonistic effect of GW7647; they showed an inhibitory effect on PPARa activation, with best compounds revealing a dose-dependent antagonistic profile. Some of these antagonists showed also an inhibitory effect on CPT1A pattern expression. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.028

文献信息

• Fibrate-derived N-(methylsulfonyl)amides with antagonistic properties on PPARα
  作者：Alessandra Ammazzalorso、Alessandra D'Angelo、Antonella Giancristofaro、Barbara De Filippis、Mauro Di Matteo、Marialuigia Fantacuzzi、Letizia Giampietro、Pasquale Linciano、Cristina Maccallini、Rosa Amoroso

  DOI：10.1016/j.ejmech.2012.10.019

  日期：2012.12

  The identification of novel PPAR ligands represents an attractive research to fully understand the complex biological pathways regulated by these receptors. Selective PPAR modulators, inverse agonists and antagonists of three PPAR isoforms could help to clarify biological effects on lipid and glucose homeostasis. Here we describe the identification of a group of N-(methylsulfonyl)amides, derived from PPAR alpha agonist carboxylic acids. Transactivation and FRET assay confirmed an antagonist behaviour on PPAR alpha for some of these compounds, with submicromolar IC50. A preliminary analysis on selectivity alpha/gamma revealed different profiles of inhibition or activation. (C) 2012 Published by Elsevier Masson SAS.