(4-(3-chlorophenyl)thiazol-2-yl)methanamine | 643725-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4-(3-chlorophenyl)thiazol-2-yl)methanamine
• 英文别名: [4-(3-chlorophenyl)-1,3-thiazol-2-yl]methanamine
• CAS: 643725-16-0
• 化学式: C₁₀H₉ClN₂S
• mdl: MFCD19104831
• 分子量: 224.714
• InChiKey: XOTXYQRNWWDGAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-(3-chlorophenyl)thiazol-2-yl)methanamine 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.33h， 生成 5-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(3-chlorophenyl)imidazo[5,1-b]thiazole
  参考文献：
  名称：

  [EN] ARYLSUBSTITUTED THIAZOLOTRIAZOLES AND THIAZOLOIMIDAZOLES
  [FR] THIAZOLOTRIAZOLES ET THIAZOLOIMIDAZOLES ARYLSUBSTITUÉS

  摘要：

  这项披露涉及用于治疗各种疾病的化合物、组合物和方法。具体而言，该披露涉及嘧啶并咪唑和嘧啶并咪唑化合物，这些化合物激活蛋白质TGR5的活性。公式（I）

  公开号：

  WO2013049585A1
• 作为产物：
  描述：

  2'-溴-3-氯苯乙酮 在 乙二胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.5h， 生成 (4-(3-chlorophenyl)thiazol-2-yl)methanamine
  参考文献：
  名称：

  [EN] ARYLSUBSTITUTED THIAZOLOTRIAZOLES AND THIAZOLOIMIDAZOLES
  [FR] THIAZOLOTRIAZOLES ET THIAZOLOIMIDAZOLES ARYLSUBSTITUÉS

  摘要：

  这项披露涉及用于治疗各种疾病的化合物、组合物和方法。具体而言，该披露涉及嘧啶并咪唑和嘧啶并咪唑化合物，这些化合物激活蛋白质TGR5的活性。公式（I）

  公开号：

  WO2013049585A1

文献信息

• [EN] AZOLE METHYLIDENE CYANIDE DERIVATIVES AND THEIR USE AS PROTEIN KINASE MODULATORS<br/>[FR] DERIVES DE CYANURE D'AZOLE METHYLIDENE ET LEUR UTILISATION COMME MODULATEURS DE PROTEINE KINASE
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2003106455A1

  公开（公告）日：2003-12-24

  The present invention is related to azole derivatives notably for use as pharmaceutically active compounds, as well as to pharmaceutical formulations containing such azole derivatives. Said azole derivatives are modulators of the protein kinase signalling pathways, particularly the one involving c-Jun N-terminal kinase and/or Glycogen Kinase Synthase 3. The present invention is furthermore related to novel azole derivatives as well as to methods of their preparation. X is O, S or NR0, with R0 being H or an unsubstituted or substituted C1 -C6 alkyl; A is 2-pyridyl, 3-pyridyl, 4-pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl group.

  本发明涉及唑衍生物，尤其是用作药物活性化合物的唑衍生物，以及包含这种唑衍生物的药物制剂。所述唑衍生物是蛋白激酶信号通路的调节剂，尤其是涉及c-Jun N端激酶和/或糖原合酶3的那一种。本发明还涉及新颖的唑衍生物以及它们的制备方法。X是O、S或NR0，其中R0是H或未取代或取代的C1-C6烷基；A是2-吡啶基，3-吡啶基，4-吡啶基，吡啶唑基，吡唑啉基，吡嗪基或三嗪基团。
• (Hetero)aryl substituted thiazol-2,4-yl scaffold as human carbonic anhydrase I, II, VII and XIV activators
  作者：Marouan Rami、Jean-Yves Winum、Claudiu T. Supuran、Patricia Melnyk、Saïd Yous

  DOI：10.1080/14756366.2018.1543292

  日期：2019.1.1

  Abstract Using histamine as lead molecule, a library of (hetero)aryl substituted thiazol-2,4-yl derivatives incorporating pyridine as proton shuttling moiety were obtained and investigated as activators of human carbonic anhydrase (CA, EC 4.2.1.1) isoforms I, II, VII and XIV. Some derivatives displayed good activating and selectivity profiles. This study provides an interesting opportunity to study

  抽象的 使用组胺作为前导分子，获得了以吡啶作为质子穿梭部分的（杂）芳基取代的噻唑-2,4-基衍生物文库，并作为人碳酸酐酶（CA，EC 4.2.1.1）同工型I，II的活化剂进行了研究。 ，VII和XIV。一些衍生物显示出良好的活化和选择性分布。这项研究提供了一个有趣的机会来研究噻唑支架设计的CA激活剂（CAA），它可能作用于中枢神经系统，并靶向涉及记忆和学习障碍的病理学。
• ARYLSUBSTITUTED THIAZOLOTRIAZOLES AND THIAZOLOIMIDAZOLES
  申请人：Smith Emilie D.

  公开号：US20130085157A1

  公开（公告）日：2013-04-04

  This disclosure relates to compounds, compositions and methods for the treatment of various disorders. In particular, the disclosure relates to thiazolotriazole and thiazoloimidazole compounds which agonize the activity of the protein TGR5.

  本公开涉及化合物、组合物和治疗各种疾病的方法。特别是，本公开涉及噻唑三唑和噻唑咪唑化合物，其激活蛋白质TGR5的活性。
• Discovery of a potent and selective small molecule hGPR91 antagonist
  作者：Debnath Bhuniya、Dhananjay Umrani、Bhavesh Dave、Deepak Salunke、Gagan Kukreja、Jayasagar Gundu、Minakshi Naykodi、Nadim S. Shaikh、Prasad Shitole、Santosh Kurhade、Siddhartha De、Sreemita Majumdar、Srinivasa B. Reddy、Suhas Tambe、Yogesh Shejul、Anita Chugh、Venkata P. Palle、Kasim A. Mookhtiar、Doris Cully、Joseph Vacca、Prasun K. Chakravarty、Ravi P. Nargund、Samuel D. Wright、Michael P. Graziano、Sheo B. Singh、Sophie Roy、Tian-Quan Cai

  DOI：10.1016/j.bmcl.2011.04.091

  日期：2011.6

  GPR91, a 7TM G-Protein-Coupled Receptor, has been recently deorphanized with succinic acid as its endogenous ligand. Current literature indicates that GPR91 plays role in various pathophysiology including renal hypertension, autoimmune disease and retinal angiogenesis. Starting from a small molecule high-throughput screening hit 1 (hGPR91 IC(50): 0.8 mu M)-originally synthesized in Merck for Bradykinin B(1) Receptor (BK(1)R) program, systematic structure-activity relationship study led us to discover potent and selective hGPR91 antagonists e.g. 2c, 4c, and 5g (IC(50): 7-35 nM; >1000 fold selective against hGPR99, a closest related GPCR; > 100 fold selective in Drug Matrix screening). This initial work also led to identification of two structurally distinct and orally bio-available lead compounds: 5g (%F: 26) and 7e (IC(50): 180 nM; > 100 fold selective against hGPR99; %F: 87). A rat pharmacodynamic assay was developed to characterize the antagonists in vivo using succinate induced increase in blood pressure. Using two representative antagonists, 2c and 4c, the GPR91 target engagement was subsequently demonstrated using the designed pharmacodynamic assay. (C) 2011 Elsevier Ltd. All rights reserved.