2-(2-cyclohexylidenehydrazinyl)-4-p-tolylthiazole | 402615-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-cyclohexylidenehydrazinyl)-4-p-tolylthiazole
• 英文别名: 2-(2-cyclohexylidenehydrazino)-4-(4-methylphenyl)thiazole；EMAC2101；2-(2-cyclohexylidenehydrazinyl)-4-p-tolyl-1,3-thiazole；N-(cyclohexylideneamino)-4-(4-methylphenyl)-1,3-thiazol-2-amine
• CAS: 402615-44-5
• 化学式: C₁₆H₁₉N₃S
• 分子量: 285.413
• InChiKey: KHLVZVWWHKJADP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (环己亚基氨基)硫脲 在 2-halo-1-(4-methylphenyl)ethan-1-one 作用下， 以 水 为溶剂， 反应 26.0h， 以76%的产率得到2-(2-cyclohexylidenehydrazinyl)-4-p-tolylthiazole
  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

• Efficient one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones in water under ultrasound irradiation
  作者：Dong-Nuan Zhang、Ji-Tai Li、Ya-Li Song、Hui-Min Liu、Hong-Ya Li

  DOI：10.1016/j.ultsonch.2011.10.017

  日期：2012.5

  A highly efficient and facile one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones was carried out in excellent yield without any catalyst in water under ultrasound irradiation.

  N-（4-芳基噻唑-2-基）hydr的高效，便捷的一锅三组分合成法在超声波照射下在水中无催化剂的情况下以优异的收率进行。
• 一种噻唑腙衍生物及其制备方法和应用
  申请人：江西农业大学

  公开号：CN113999187A

  公开（公告）日：2022-02-01

  本发明涉及化学合成和医药技术领域，尤其涉及一种噻唑腙衍生物及其制备方法和应用。所述噻唑腙衍生物的制备步骤包括：(1)将氨基硫脲、α‑溴代苯乙酮和酮类物质混合后，冷凝回流；(2)待反应结束后，通过旋蒸去除多余酮类物质或溶剂，反应物经乙酸乙酯冲洗后，用乙醇重结晶，即得噻唑腙衍生物；所述酮类物质为丙酮，戊酮，庚酮，环己酮中的一种；其中，所述酮类物质为环己酮时，还需要加入乙腈作为溶剂。本发明的噻唑腙衍生物对水稻纹枯病菌的抑制效果明显，因此开发新型抗菌剂，或其与农业上可接受的助剂或增效剂以及与商品杀菌剂组合用于防治植物真菌中具有非常好的应用前景。
• 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.
• Synthesis and biological evaluation of some novel 1-indanone thiazolylhydrazone derivatives as anti-Trypanosoma cruzi agents
  作者：María E. Caputto、Alejandra Ciccarelli、Fernanda Frank、Albertina G. Moglioni、Graciela Y. Moltrasio、Daniel Vega、Elisa Lombardo、Liliana M. Finkielsztein

  DOI：10.1016/j.ejmech.2012.07.013

  日期：2012.9

  A series of novel 4-arylthiazolylhydrazones (TZHs) derived from 1-indanones were synthesized in good yields (66-92%) in a simple procedure using microwave irradiation and then characterized by spectroscopy studies. The compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against the epimastigote, trypomastigote and amastigote forms of the parasite. Most TZHs displayed excellent activity, and were more potent and selective than the reference drug Benznidazole, used in the current chemotherapy. Analysis of the free sterols from parasite incubated with the compounds showed that inhibition of ergosterol biosynthesis is a possible target for the action of these new TZHs. In particular, TZH 9 emerged as a promising antichagasic compound to be evaluated in animal models. (C) 2012 Elsevier Masson SAS. All rights reserved.