2-[(5-chlorobenzo[d]thiazol-2-yl)thio]-2-phenylacetic acid

• 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-chlorobenzo[d]thiazol-2-yl)thio]-2-phenylacetic acid
• 英文别名: 2-(5-Chlorobenzothiazol-2-ylthio)-2-phenylacetic acid；[(5-chloro-1,3-benzothiazol-2-yl)thio](phenyl)acetic Acid；α-(5-chlorobenzothiazol-2-ylthio)benzeneacetic acid；rac-[(5-Chloro-1,3-benzothiazol-2-yl)thio](phenyl)acetic Acid；2-[(5-chloro-1,3-benzothiazol-2-yl)sulfanyl]-2-phenylacetic acid
• 化学式: C₁₅H₁₀ClNO₂S₂
• 分子量: 335.835
• InChiKey: RZBXFBBFXGSOEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(5-chlorobenzo[d]thiazol-2-yl)thio]-2-phenylacetic acid 生成 α-(5-chlorobenzothiazol-2-ylthio)benzeneacetic acid sodium salt
  参考文献：
  名称：

  WEI, P. H. L.;GREGORY, F. J.

  摘要：

  DOI：
• 作为产物：
  描述：

  α-溴苯乙酸乙酯 在 乙醇 、 sodium 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-[(5-chlorobenzo[d]thiazol-2-yl)thio]-2-phenylacetic 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

• .alpha.-Phenyl-2-(aza)benzothiazolylthioglycolic acids and derivatives
  申请人：American Home Products Corporation

  公开号：US04567267A1

  公开（公告）日：1986-01-28

  Novel .alpha.-phenyl-2-(aza)benzothiazolylthioglycolic acids, derivatives thereof and pharmacologically acceptable salts thereof are disclosed, as well as their use as intermediates in the preparation of 2-substituted-3-hydroxy-thiazolo[2,3-b]-benzothiazolium salts, 2-substituted-thiazolo[2,3-b]benzothiazol-3(2H)-one mesoionic didehydro derivatives, 2-substituted-thiazolo[2',3'-2,3]thiazolo[5,4-b]pyridin-3(2H)-one mesoionic didehydro derivatives and related compounds, and their use as modulators of the immune response.

  新型α-苯基-2-(氮杂)苯并噻唑硫代乙酸及其衍生物和药理学上可接受的盐被披露，以及它们作为2-取代-3-羟基噻唑并[2,3-b]-苯并噻唑盐、2-取代噻唑并[2,3-b]苯并噻唑-3(2H)-酮中间体的用途，2-取代噻唑并[2',3'-2,3]噻唑并[5,4-b]吡啶-3(2H)-酮中间体和相关化合物，以及它们作为免疫应答调节剂的用途。
• Synthesis of novel benzothiazole amides: Evaluation of PPAR activity and anti-proliferative effects in paraganglioma, pancreatic and colorectal cancer cell lines
  作者：Alessandra Ammazzalorso、Laura De Lellis、Rosalba Florio、Antonio Laghezza、Barbara De Filippis、Marialuigia Fantacuzzi、Letizia Giampietro、Cristina Maccallini、Paolo Tortorella、Serena Veschi、Fulvio Loiodice、Alessandro Cama、Rosa Amoroso

  DOI：10.1016/j.bmcl.2019.06.020

  日期：2019.8

  activation of PPARs has a positive impact on cancer cell growth and viability in multiple preclinical tumor models, suggesting a new therapeutic potential for PPAR antagonists. In the present study, the benzothiazole amides 2a-g were synthesized and their activities on PPARs were investigated. Transactivation assay showed a moderate activity of the novel compounds as PPARα antagonists. Notably, in cellular

  PPAR的激活减少对多种临床前肿瘤模型中的癌细胞生长和生存能力具有积极影响，这表明PPAR拮抗剂具有新的治疗潜力。在本研究中，合成了苯并噻唑酰胺2a-g并研究了其对PPAR的活性。反式激活试验表明该新型化合物具有中等活性，可作为PPARα拮抗剂。值得注意的是，在细胞分析中，它们在过量表达PPARα的胰腺癌，结肠直肠癌和副神经节瘤癌细胞中表现出细胞毒性。尤其是，化合物2b在两种副神经节瘤细胞系中表现出最显着的活力抑制作用（大于90％），IC 50值在低微摩尔范围内。另外2b同一细胞中的集落形成能力明显受损。综上所述，这些结果表明化合物2b具有相关的抗增殖潜力，在副神经节瘤中是特别有效的，副神经节瘤是一种对化疗反应不良的罕见肿瘤。
• Inhibition of bone loss by
  申请人：American Home Products Corporation

  公开号：US04866082A1

  公开（公告）日：1989-09-12

  A method for modifying the balance between bone production and bone resorption in a host animal by administration of (-)-N-[[(5-chloro-benzothiazolyl)-thio]phenylacetyl]-L-cysteine to inhibit bone loss.

  通过给宿主动物注射(-)-N-[[(5-氯苯并噻唑基)-硫]苯乙酰]-L-半胱氨酸，以抑制骨质流失，从而改变骨生产和骨吸收之间的平衡的方法。
• Inhibitor of mammalian collagenase and elastase
  申请人：American Home Products Corporation

  公开号：US04609667A1

  公开（公告）日：1986-09-02

  A method of inhibiting mammalian elastase and collagenase by using [benzothiazolylthio]phenylacetyl-L-cysteines and the pharmaceutically acceptable salts thereof.

  一种使用[苯并噻唑基硫代]苯基乙酰-L-半胱氨酸及其药学上可接受的盐来抑制哺乳动物弹性蛋白酶和胶原酶的方法。
• Inhibitors of mammalian collagenase
  申请人：American Home Products Corporation

  公开号：US04367233A1

  公开（公告）日：1983-01-04

  A method of inhibiting mammalian collagenase by using .alpha.-phenyl-2-(aza)benzothiazolylthioglycolic acids and derivatives thereof, and the pharmaceutically acceptable salts thereof.

  使用.alpha.-苯基-2-(aza)苯并噻唑基巯基乙酸及其衍生物及其药学上可接受的盐，抑制哺乳动物胶原酶的方法。