2-[(5-chloro-1,3-benzothiazol-2-yl)thio]-3-methyl-N-(phenylsulfonyl)butanamide | 1331733-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]-3-methyl-N-(phenylsulfonyl)butanamide
• 英文别名: N-(benzenesulfonyl)-2-[(5-chloro-1,3-benzothiazol-2-yl)sulfanyl]-3-methylbutanamide
• CAS: 1331733-90-4
• 化学式: C₁₈H₁₇ClN₂O₃S₃
• 分子量: 440.996
• InChiKey: CNCBRXVUTZRPQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-溴代异戊酸乙酯 在 4-二甲氨基吡啶 、 乙醇 、 sodium 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]-3-methyl-N-(phenylsulfonyl)butanamide
  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

• Titanium-Promoted Acylation of Sulfonamides to<i>N</i>-Acylsulfonamide PPAR<font>α</font>Antagonists
  作者：Alessandra Ammazzalorso、Maria Luisa Tricca、Isabella Bruno、Barbara De Filippis、Mauro Di Matteo、Marialuigia Fantacuzzi、Letizia Giampietro、Cristina Maccallini、Adriano Mollica、Rosa Amoroso

  DOI：10.1080/00397911.2015.1092552

  日期：2015.11.17

  The direct acylation of sulfonamides by esters represents an attractive strategy in organic chemistry, being an interesting alternative to classical approaches to N-acylsulfonamides. Here is described a simple and effective method to obtain N-acylsulfonamides of pharmaceutical interest, in a reaction promoted by titanium(IV) chloride. This strategy was successfully applied to the synthesis of a peroxisome proliferator-activated receptor antagonist with a benzenesulfonimide moiety, ensuring an excellent yield of product. The reaction was further studied to explore the behavior of different -bromoesters and esters and the effects of para-substitution in the benzenesulfonamide moiety.
• Benzothiazole-based N-(phenylsulfonyl)amides as a novel family of PPARα antagonists
  作者：Alessandra Ammazzalorso、Antonella Giancristofaro、Alessandra D’Angelo、Barbara De Filippis、Marialuigia Fantacuzzi、Letizia Giampietro、Cristina Maccallini、Rosa Amoroso

  DOI：10.1016/j.bmcl.2011.06.028

  日期：2011.8

  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.