4-phenyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole | 957761-53-4

• 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-phenyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole
• 英文别名: 4-phenyl-N-(1-pyridin-4-ylethylideneamino)-1,3-thiazol-2-amine
• CAS: 957761-53-4
• 化学式: C₁₆H₁₄N₄S
• 分子量: 294.38
• InChiKey: XYZOHIFSMWJKGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-乙酰基吡啶 在 溶剂黄146 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 4-phenyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazinyl)thiazole
  参考文献：
  名称：

  肼基芳基噻唑基吡啶支架：合成，结构表征，体外α-葡萄糖苷酶抑制活性和计算机研究

  摘要：

  阿卡波糖，米格列醇和伏格列波糖是α-葡萄糖苷酶的抑制剂，并在临床上用于II型糖尿病的治疗。但是，许多不利影响也与之相关。因此，开发新的治疗剂是药物化学研究的最大兴趣。当前的研究是基于新α-葡萄糖苷酶抑制剂的鉴定。为此，通过两步反应合成了基于肼基芳基噻唑的吡啶衍生物1–39，并通过光谱技术EI-MS，HREI-MS，1 H-和13 C NMR进行了全面表征。然而，NOESY证实了亚胺键的立体化学。所有化合物均经过体外α葡萄糖苷酶抑制活性，并发现有源很多倍（IC 50  = 1.40±0.01-236.10±2.20  μ M）相比，具有IC的标准阿卡波糖50的856.45±5.60值 μ M的限定的结构-活性关系是为了推测取代基对抑制活性的影响而进行的实验，预测与负诱导作用较小的取代基相比，负诱导作用较大的取代基在活性中起重要作用。但是，为了更好地了解配体酶的相互作用，还进行了分子对接研究。

  DOI：

  10.1016/j.ejmech.2017.06.041

文献信息

• Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents
  作者：Sobhi M. Gomha、Fathy M. Abdelrazek、Aly H. Abdelrahman、Peter Metz

  DOI：10.3987/com-16-13443

  日期：——

  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.
• Exploring 4-substituted-2-thiazolylhydrazones from 2-, 3-, and 4-acetylpyridine as selective and reversible hMAO-B inhibitors
  作者：Paola Chimenti、Anél Petzer、Simone Carradori、Melissa D’Ascenzio、Romano Silvestri、Stefano Alcaro、Francesco Ortuso、Jacobus P. Petzer、Daniela Secci

  DOI：10.1016/j.ejmech.2013.05.032

  日期：2013.8

  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.