4-methyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole | 1449302-94-6

• 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-methyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole
• CAS: 1449302-94-6
• 化学式: C₁₁H₁₂N₄S
• 分子量: 232.309
• InChiKey: SRBTUFCYRZJVEF-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±34.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.17
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole 、 氯化重氮苯 在 吡啶 作用下， 以 水 为溶剂， 反应 0.5h， 生成 4-methyl-5-(phenyldiazenyl)-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole
  参考文献：
  名称：

  Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents

  摘要：

  A novel series of 2-ethylidenehydrazono-5-arylazothiazoles 5a-h and 2-ethylidenehydrazono-5-arylazothiazolones 9a-d were prepared by cyclocondensation of hydrazonyl halides 3a-h and 7a-d with ethylidenethiosemicarbazide 2. In addition, reaction of 2 with N-phenyl-carbohydrazonyl chloride (14), afforded 1,3,4-thiadiazole derivative 17 as the end product. Moreover, the thiosemicarbazide derivative 2 was reacted with various bromoacetyl compounds 19a-d and 1,1'-(1,4-phenylene)bis(2-bromoethanone) (21) furnished the respective thiazole derivatives 20a-d and 1,4-phenylene-bis-thiazole derivative 22. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 5h, 5d, 5g, 5f and 5e with IC50 equal 2.23 +/- 0.28, 2.48 +/- 0.34, 2.49 +/- 0.24, 4.03 +/- 0.11, and 5.32 +/- 0.27 mu M, respectively.

  DOI：

  10.3987/com-16-13443
• 作为产物：
  描述：

  4-乙酰吡啶 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4-methyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole
  参考文献：
  名称：

  Exploring 4-substituted-2-thiazolylhydrazones from 2-, 3-, and 4-acetylpyridine as selective and reversible hMAO-B inhibitors

  摘要：

  A series of 4-substituted-2-thiazolylhydrazone derivatives have been synthesized and tested in vitro for their human monoamine oxidase (hMAO) A and B inhibitory activity. Our findings confirmed that the substitution at C4 of the thiazole ring was important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Moreover, these derivatives were endowed with a reversible mechanism of enzyme inhibition. Molecular modelling studies were performed to rationalize the recognition of all inhibitors with respect to hMAO-A and -B isoforms. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.032