(E)-2-(2-(1-(p-tolyl)ethylidene)hydrazinyl)benzo[d]thiazole | 1609564-58-0

• 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: (E)-2-(2-(1-(p-tolyl)ethylidene)hydrazinyl)benzo[d]thiazole
• 英文别名: 2-{(2E)-2-[1-(4-methylphenyl)ethylidene]hydrazinyl}-1,3-benzothiazole；N-[(E)-1-(4-methylphenyl)ethylideneamino]-1,3-benzothiazol-2-amine
• CAS: 1609564-58-0
• 化学式: C₁₆H₁₅N₃S
• 分子量: 281.381
• InChiKey: YORUQFAJOBESTQ-LDADJPATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(1-(p-tolyl)ethylidene)hydrazinyl)benzo[d]thiazole 在 Jones reagent 、 三氯氧磷 作用下， 以 氘代氯仿 、 丙酮 为溶剂， 反应 18.0h， 生成 1-(benzo[d]thiazol-2-yl)-3-(p-tolyl)-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Identification of trisubstituted-pyrazol carboxamide analogs as novel and potent antagonists of farnesoid X receptor

  摘要：

  Farnesoid X receptor (FXR, NRIH4) plays a major role in the control of cholesterol metabolism. This suggests that antagonizing the transcriptional activity of FXR is a potential means to treat cholestasis and related metabolic disorders. Here we describe the synthesis, biological evaluation, and structure-activity relationship (SAR) studies of trisubstituted-pyrazol carboxamides as novel and potent FXR antagonists. One of these novel FXR antagonists, 4j has an IC50 of 7.5 nM in an FXR binding assay and 468.5 nM in a cell-based FXR antagonistic assay. Compound 4j has no detectable FXR agonistic activity or cytotoxicity. Notably, 4j is the most potent FXR antagonist identified to date; it has a promising in vitro profile and could serve as an excellent chemical tool to elucidate the biological function of FXR. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.014
• 作为产物：
  描述：

  2-肼基苯并噻唑 、 对甲基苯乙酮 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 18.0h， 以99%的产率得到(E)-2-(2-(1-(p-tolyl)ethylidene)hydrazinyl)benzo[d]thiazole
  参考文献：
  名称：

  Identification of trisubstituted-pyrazol carboxamide analogs as novel and potent antagonists of farnesoid X receptor

  摘要：

  Farnesoid X receptor (FXR, NRIH4) plays a major role in the control of cholesterol metabolism. This suggests that antagonizing the transcriptional activity of FXR is a potential means to treat cholestasis and related metabolic disorders. Here we describe the synthesis, biological evaluation, and structure-activity relationship (SAR) studies of trisubstituted-pyrazol carboxamides as novel and potent FXR antagonists. One of these novel FXR antagonists, 4j has an IC50 of 7.5 nM in an FXR binding assay and 468.5 nM in a cell-based FXR antagonistic assay. Compound 4j has no detectable FXR agonistic activity or cytotoxicity. Notably, 4j is the most potent FXR antagonist identified to date; it has a promising in vitro profile and could serve as an excellent chemical tool to elucidate the biological function of FXR. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.014

文献信息

• [EN] FARNESOID X RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR X DE FARNÉSOÏDE
  申请人：HOPE CITY

  公开号：WO2015116856A3

  公开（公告）日：2015-11-05
• Compounds Having Activity in Correcting Mutant-Cftr Processing and Uses Thereof
  申请人：Verkman Alan

  公开号：US20080318984A1

  公开（公告）日：2008-12-25

  The invention provides compositions, pharmaceutical preparations and methods for correcting cellular processing (e.g., folding, trafficking, or post-translational modification) of a mutant-cystic fibrosis transmembrane conductance regulator protein (e.g., ΔF508 CFTR) that are useful for the treatment of cystic fibrosis (CF). The compositions and pharmaceutical preparations of the invention may comprise one or more aminobenzothiazole-containing compounds, aminoarylthiazole-containing compounds, quinazolinylaminopyrimidinone-containing compounds, bisaminomethylbithiazole-containing compounds, or phenylaminoquino-line-containing compounds of the invention, or an analog or derivative thereof.
• US8143295B2
  申请人：——

  公开号：US8143295B2

  公开（公告）日：2012-03-27
• Identification of trisubstituted-pyrazol carboxamide analogs as novel and potent antagonists of farnesoid X receptor
  作者：Donna D. Yu、Wenwei Lin、Barry M. Forman、Taosheng Chen

  DOI：10.1016/j.bmc.2014.04.014

  日期：2014.6

  Farnesoid X receptor (FXR, NRIH4) plays a major role in the control of cholesterol metabolism. This suggests that antagonizing the transcriptional activity of FXR is a potential means to treat cholestasis and related metabolic disorders. Here we describe the synthesis, biological evaluation, and structure-activity relationship (SAR) studies of trisubstituted-pyrazol carboxamides as novel and potent FXR antagonists. One of these novel FXR antagonists, 4j has an IC50 of 7.5 nM in an FXR binding assay and 468.5 nM in a cell-based FXR antagonistic assay. Compound 4j has no detectable FXR agonistic activity or cytotoxicity. Notably, 4j is the most potent FXR antagonist identified to date; it has a promising in vitro profile and could serve as an excellent chemical tool to elucidate the biological function of FXR. (C) 2014 Elsevier Ltd. All rights reserved.