2-(2-cyclohexylidenehydrazinyl)-4-(4-nitrophenyl)thiazole | 355811-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-cyclohexylidenehydrazinyl)-4-(4-nitrophenyl)thiazole
• 英文别名: EMAC2100；N-(cyclohexylideneamino)-4-(4-nitrophenyl)-1,3-thiazol-2-amine
• CAS: 355811-38-0
• 化学式: C₁₅H₁₆N₄O₂S
• 分子量: 316.384
• InChiKey: OMICYHDRQXQVRP-UHFFFAOYSA-N

物化性质

• 熔点：
  172-173 °C
• 沸点：
  514.9±42.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (环己亚基氨基)硫脲 在 2-halo-1-(4-nitrophenyl)ethan-1-one 作用下， 以 水 为溶剂， 反应 26.0h， 以83%的产率得到2-(2-cyclohexylidenehydrazinyl)-4-(4-nitrophenyl)thiazole
  参考文献：
  名称：

  Exploring the thiazole scaffold for the identification of new agents for the treatment of fluconazole resistant Candida

  摘要：

  Cyclohexyliden- and 2-methylcyclohexyliden-hydrazo-4-arylthiazoles were synthesized and tested as antifungal agents. All compounds exhibited minimal inhibitory concentration (MIC) values comparable with those of fluconazole (FLC). Moreover, some compounds showed fungicidal activity at low concentration. Worth noting five out of nine compounds were active towards Candida albicans 25 FLC resistant isolated from clinical specimens. The cellular toxicity was evaluated and none of the compounds is toxic at the MIC. On the basis of our data we can conclude that these derivatives are promising agents for the treatment of resistant C. albicans.

  DOI：

  10.3109/14756366.2015.1113171

文献信息

• 脂环酮腙噻唑衍生物作为酪氨酸酶抑制剂的应用
  申请人：邵阳学院

  公开号：CN108409683A

  公开（公告）日：2018-08-17

  本发明公开了一种具有酪氨酸酶抑制活性的脂环酮腙噻唑类衍生物。体外抑制酪氨酸酶的筛选结果表明：所合成的脂环酮腙噻唑类衍生物部分具有酪氨酸酶抑制活性。本发明所涉及的化合物制备简单，在药物、化妆品、食品保鲜及生物杀虫剂领域具有一定的应用前景。所述脂环酮腙噻唑衍生物的化学结构式如下述结构所示，其中n与R由说明书所定义。式(Ⅰ)。
• Visiblelight-induced ternary electron donor–acceptor complex enabled synthesis of 2-(2-hydrazinyl) thiazole derivatives and the assessment of their antioxidant and antidiabetic therapeutic potential
  作者：Sovan Dey、Arindam Das、Ram Naresh Yadav、Palash Jyoti Boruah、Prerana Bakli、Tania Baishya、Koushik Sarkar、Anup Barman、Ranabir Sahu、Biplab Maji、Amit Kumar Paul、Md. Firoj Hossain

  DOI：10.1039/d2ob02308c

  日期：——

  A mild and eco-friendly visible-light-induced synthesis of 2-(2-hydrazinyl) thiazole from readily accessible thiosemicarbazide, carbonyl, and phenacyl bromide in the absence of a metal catalyst and/or any extrinsic photosensitizer is reported. This approach only requires a source of visible light and a green solvent at room temperature to produce the medicinally privileged scaffolds of hydrazinyl-thiazole

  报道了在没有金属催化剂和/或任何外在光敏剂的情况下，从容易获得的氨基硫脲、羰基和苯甲酰溴合成 2-(2-肼基) 噻唑的温和且环保的可见光诱导合成。这种方法只需要一个可见光源和室温下的绿色溶剂，就可以以优异的收率生产具有药用价值的肼基-噻唑衍生物支架。实验研究支持原位形成吸收可见光的光敏彩色三元 EDA 复合物。下一步是制备一对处于激发态的自由基，这使得通过 SET 和 PCET 过程制备噻唑衍生物变得更加容易。DFT 计算还支持反应过程的机理分析。在体外测试了合成库中某些化合物的抗氧化和抗糖尿病特性。所有研究的化合物都表现出明显的抗氧化活性，如还原力实验和DPPH 自由基清除实验的IC 50值所证明的。此外， 4c、4d和4g的IC 50值也表现出强烈的α-淀粉酶抑制作用。
• Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Simone Carradori、Elias Maccioni、M. Cristina Cardia、Matilde Yáñez、Francisco Orallo、Stefano Alcaro、Francesco Ortuso、Roberto Cirilli、Rosella Ferretti、Simona Distinto、Johannes Kirchmair、Thierry Langer

  DOI：10.1016/j.bmc.2010.05.070

  日期：2010.7

  The present study reports on synthesis in high yields (70-99%), HPLC enantioseparation, inhibitory activity against human monoamino oxidases, and molecular modeling including 3D-QSAR studies, of a large series of (4-aryl-thiazol-2-yl) hydrazones (1-45). Most of the synthesized compounds proved to be potent and selective inhibitors of hMAO-B isoform in the micromolar or nanomolar range, thus demonstrating that hydrazothiazole could be considered a good pharmacophore to design new hMAO-B inhibitors. Due to the presence in some derivatives of a chiral center, we also performed a semipreparative chromatographic enantioseparation of these compounds obtained by a stereoconservative pattern. The separated enantiomers were submitted to in vitro biological evaluation to point out the stereorecognition of the active site of the enzyme towards these structures. Finally, a 3D-QSAR study was carried out using Comparative Molecular Field Analysis (CoMFA), aiming to deduce rational guidelines for the further structural modification of these lead compounds. (C) 2010 Elsevier Ltd. All rights reserved.