ethyl 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]pentanoate | 1192215-05-6

• 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: ethyl 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]pentanoate
• 英文别名: Ethyl 2-[(5-chloro-1,3-benzothiazol-2-yl)sulfanyl]pentanoate
• CAS: 1192215-05-6
• 化学式: C₁₄H₁₆ClNO₂S₂
• 分子量: 329.872
• InChiKey: OJWPFENRHFIZAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]pentanoate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以59%的产率得到2-[(5-chloro-1,3-benzothiazol-2-yl)thio]pentanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Heteroarylthioalkanoic Acid Analogues of Clofibric Acid as Peroxisome Proliferator-Activated Receptor α Agonists

  摘要：

  A series of 2-heteroarylthioalkanoic acids were synthesized through systematic structural modifications of clofibric acid and evaluated for human peroxisome proliferator-activated receptor alpha (PPAR alpha) transactivation activity, with the aim of obtaining new hypolipidemic compounds. Some thiophene and benzothiazole derivatives showing a good activation of the receptor a were screened for activity against the PPAR gamma isoform. The gene induction of selected compounds was also investigated in the human hepatoma cell line.

  DOI：

  10.1021/jm900878u
• 作为产物：
  描述：

  2-溴戊酸乙酯 、 2-巯基-5-氯苯并噻唑 在 乙醇 、 sodium 作用下， 反应 4.0h， 以89%的产率得到ethyl 2-[(5-chloro-1,3-benzothiazol-2-yl)thio]pentanoate
  参考文献：
  名称：

  Cytotoxic effect of a family of peroxisome proliferator-activated receptor antagonists in colorectal and pancreatic cancer cell lines

  摘要：

  Recent studies report an interesting role of peroxisome proliferator‐activated receptor (PPAR) antagonists in different tumor models, being these compounds able to perturb metabolism and viability in cancer cells. In this work, the identification of a novel PPAR antagonist, showing inhibitory activity on PPARα and a weaker antagonism on PPARγ, is described. The activity of this compound and of a series of chemical analogues was investigated in selected tumor cell lines, expressing both PPARα and PPARγ. Data obtained show a dose‐dependent cytotoxic effect of the novel PPAR antagonist in colorectal and pancreatic cancer models.

  DOI：

  10.1111/cbdd.13026

文献信息

• 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.
• Synthesis and Biological Evaluation of 2-Heteroarylthioalkanoic Acid Analogues of Clofibric Acid as Peroxisome Proliferator-Activated Receptor α Agonists
  作者：Letizia Giampietro、Alessandra Ammazzalorso、Antonella Giancristofaro、Fabio Lannutti、Giancarlo Bettoni、Barbara De Filippis、Marialuigia Fantacuzzi、Cristina Maccallini、Michele Petruzzelli、Annalisa Morgano、Antonio Moschetta、Rosa Amoroso

  DOI：10.1021/jm900878u

  日期：2009.10.22

  A series of 2-heteroarylthioalkanoic acids were synthesized through systematic structural modifications of clofibric acid and evaluated for human peroxisome proliferator-activated receptor alpha (PPAR alpha) transactivation activity, with the aim of obtaining new hypolipidemic compounds. Some thiophene and benzothiazole derivatives showing a good activation of the receptor a were screened for activity against the PPAR gamma isoform. The gene induction of selected compounds was also investigated in the human hepatoma cell line.
• Cytotoxic effect of a family of peroxisome proliferator-activated receptor antagonists in colorectal and pancreatic cancer cell lines
  作者：Alessandra Ammazzalorso、Laura De Lellis、Rosalba Florio、Isabella Bruno、Barbara De Filippis、Marialuigia Fantacuzzi、Letizia Giampietro、Cristina Maccallini、Silvia Perconti、Fabio Verginelli、Alessandro Cama、Rosa Amoroso

  DOI：10.1111/cbdd.13026

  日期：2017.11

  Recent studies report an interesting role of peroxisome proliferator‐activated receptor (PPAR) antagonists in different tumor models, being these compounds able to perturb metabolism and viability in cancer cells. In this work, the identification of a novel PPAR antagonist, showing inhibitory activity on PPARα and a weaker antagonism on PPARγ, is described. The activity of this compound and of a series of chemical analogues was investigated in selected tumor cell lines, expressing both PPARα and PPARγ. Data obtained show a dose‐dependent cytotoxic effect of the novel PPAR antagonist in colorectal and pancreatic cancer models.