2-乙炔基-4-甲基噻唑 | 211940-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-乙炔基-4-甲基噻唑
• 英文名称: 2-ethynyl-4-methyl-1,3-thiazole
• 英文别名: 2-Ethynyl-4-methylthiazole
• CAS: 211940-25-9
• 化学式: C₆H₅NS
• 分子量: 123.178
• InChiKey: GXICJSRJEHQZMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙炔基-4-甲基噻唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二甲基亚砜 、 三乙胺 、 palladium dichloride 作用下， 反应 51.5h， 生成 1-(4-hydroxyphenyl)-2-(4-methyl-1,3-thiazol-2-yl)ethane-1,2-dione
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel 4-thiazolylimidazoles as inhibitors of transforming growth factor-β type I receptor kinase

  摘要：

  A novel series of 4-thiazolylimidazoles was synthesized as transforming growth factor-beta (TGF-beta) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitors. These compounds were evaluated for their ALK5 inhibitory activity in an enzyme assay and their TGF-beta-induced Smad2/3 phosphorylation inhibitory activity in a cell-based assay. N-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1, 3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}butanamide 20, a potent and selective ALK5 inhibitor, exhibited good enzyme inhibitory activity (IC50 = 8.2 nM) as well as inhibitory activity against TGF-beta-induced Smad2/3 phosphorylation at a cellular level (IC50 = 32 nM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.066
• 作为产物：
  描述：

  4-methyl-2-((trimethylsilyl)ethynyl)thiazole 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以88%的产率得到2-乙炔基-4-甲基噻唑
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel 4-thiazolylimidazoles as inhibitors of transforming growth factor-β type I receptor kinase

  摘要：

  A novel series of 4-thiazolylimidazoles was synthesized as transforming growth factor-beta (TGF-beta) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitors. These compounds were evaluated for their ALK5 inhibitory activity in an enzyme assay and their TGF-beta-induced Smad2/3 phosphorylation inhibitory activity in a cell-based assay. N-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1, 3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}butanamide 20, a potent and selective ALK5 inhibitor, exhibited good enzyme inhibitory activity (IC50 = 8.2 nM) as well as inhibitory activity against TGF-beta-induced Smad2/3 phosphorylation at a cellular level (IC50 = 32 nM). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.066

文献信息

• [EN] HETEROARYL COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROARYLE ET UTILISATIONS ASSOCIÉES
  申请人：CELGENE AVILOMICS RES INC

  公开号：WO2014144737A1

  公开（公告）日：2014-09-18

  The present invention relates to compounds useful as inhibitors of protein kinases, containing a cysteine residue in the ATP binding site. The invention further provides for pharmaceutically acceptable compositions comprising therapeutically effective amounts of one or more of the protein kinase inhibitor compounds and methods of using said compositions in the treatment of cancers and carcinomas.

  本发明涉及作为蛋白激酶抑制剂的化合物，这些化合物在ATP结合位点包含一个半胱氨酸残基。该发明还提供了包含一种或多种蛋白激酶抑制剂化合物的药用可接受组合物，以及使用所述组合物治疗癌症和癌的方法。
• [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2015051244A1

  公开（公告）日：2015-04-09

  Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

  调节激酶活性的化合物和药物组合物，包括PI3激酶活性，以及与激酶活性相关的疾病和病况的化合物、药物组合物和治疗方法在此进行描述。
• [EN] HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF PI3K-GAMMA MEDIATED DISORDERS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT DE TROUBLES MÉDIÉS PAR PI3K-GAMMA
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2015143012A1

  公开（公告）日：2015-09-24

  Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

  本文描述了调节激酶活性的化合物和药物组合物，包括PI3激酶活性，以及与激酶活性相关的疾病和状况的治疗方法，包括PI3激酶活性的化合物、药物组合物和治疗方法。
• [EN] MK2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS MK2 ET UTILISATIONS ASSOCIÉES
  申请人：CELGENE AVILOMICS RES INC

  公开号：WO2014149164A1

  公开（公告）日：2014-09-25

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用方法。
• INHIBITORS OF THE FIBROBLAST GROWTH FACTOR RECEPTOR
  申请人：Bifulco, Jr. Neil

  公开号：US20150119405A1

  公开（公告）日：2015-04-30

  Described herein are inhibitors of FGFR-4, pharmaceutical compositions including such compounds, and methods of using such compounds and compositions.

  本处描述的是FGFR-4的抑制剂，包括含有此类化合物的药物组合物，以及使用此类化合物和组合物的方法。