2-(2-(4-methylbenzylidene)hydrazinyl)-4-phenylthiazole | 171628-39-0

• 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-(4-methylbenzylidene)hydrazinyl)-4-phenylthiazole
• 英文别名: benzaldehyde-4-methyl-(4-phenyl-3-thiazolyl)hydrazone；2-(p-methylbenzylidenehydrazino)-4-phenylthiazole；2-(4-methylbenzyliden)hydrazo-4-phenylthiazole；N-[(4-methylphenyl)methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• CAS: 171628-39-0
• 化学式: C₁₇H₁₅N₃S
• 分子量: 293.392
• InChiKey: PPHMPCRULIYQPF-UHFFFAOYSA-N

物化性质

• 熔点：
  202-205 °C(Solv: ethanol (64-17-5))
• 沸点：
  473.4±48.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 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：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(4-methylbenzylidene)hydrazinyl)-4-phenylthiazole 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以78%的产率得到3-(4-methylphenyl)-5-phenyl-[1,3]thiazolo[2,3-c][1,2,4]triazole
  参考文献：
  名称：

  Hypervalent Iodine in the Synthesis of Bridgehead Heterocycles: A New Synthesis of 3, 5-Diarylthiazolo[2, 3-C]-s-triazoles

  摘要：

  The synthesis of 3,5-diarylthiazolo[2,3-c]-s-triazoles (3a-f) has been accomplished by using a new method involving oxidation of arenecarbaldehyde-4-arylthiazol-2-ylhydrazones (2a-f) with iodobenzene diacetate (IBD) in dichloromethane by intramolecular cyclization in high yields.

  DOI：

  10.1080/00397919508013857
• 作为产物：
  描述：

  4-methylbenzaldehyde thiosemicarbazone 、 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 以 乙醇 为溶剂， 生成 2-(2-(4-methylbenzylidene)hydrazinyl)-4-phenylthiazole
  参考文献：
  名称：

  Hypervalent Iodine in the Synthesis of Bridgehead Heterocycles: A New Synthesis of 3, 5-Diarylthiazolo[2, 3-C]-s-triazoles

  摘要：

  The synthesis of 3,5-diarylthiazolo[2,3-c]-s-triazoles (3a-f) has been accomplished by using a new method involving oxidation of arenecarbaldehyde-4-arylthiazol-2-ylhydrazones (2a-f) with iodobenzene diacetate (IBD) in dichloromethane by intramolecular cyclization in high yields.

  DOI：

  10.1080/00397919508013857

文献信息

• Synthesis, Antibacterial Activity and Quantum-Chemical Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues
  作者：Mohammad Sayed Alam、Lijun Liu、Yong-Eok Lee、Dong-Ung Lee

  DOI：10.1248/cpb.59.568

  日期：——

  A new series of 2-arylidenehydrazinyl-4-arylthiazole derivatives (2a—k) was designed and synthesized through a rapid, simple, and efficient methodology in excellent isolated yield. These compounds were screened for in vitro antimicrobial activities against eight bacteria, e.g. Bacillus cereus, Staphylococcus aureus, Bacillus subtilis, Bacillus megaterium, Pseudomonas aeruginosa, Shigella dysenteriae, Salmonella typhi, Escherichia coli, and three fungi e.g. Aspergillus oryzae, Candida albicans, and Saccharomyces cerevis. The results indicate that some of the compounds exhibit strong antibacterial activity, depending on the bacterial strain, but show virtually no antifungal activity. The structure–antibacterial activity relationships were studied using some physicochemical and quantum-chemical parameters with the ab initio Hartree–Fock model at the RHF/6-31G level of theory. A good qualitative correlation between predicted lipophilic parameters and antibacterial activity has been found.

  通过快速、简单且高效的方法，设计并合成了一系列新的2-芳亚甲基酰肼-4-芳基噻唑衍生物（2a—k），这些化合物在极佳的分离产率下制得。我们对这些化合物进行了体外抗菌活性筛选，针对八种细菌（如蜡样芽孢杆菌、金黄色葡萄球球菌、枯草芽孢杆菌、巨大芽孢杆菌、铜绿假单胞菌、痢疾志贺菌、伤寒沙门菌、大肠埃希菌）和三种真菌（如米曲霉、白色念珠菌、酿酒酵母）进行了测试。结果显示，部分化合物根据细菌株的不同，展现出强烈的抗菌活性，但几乎不具备抗真菌活性。我们采用从头计算Hartree-Fock模型在RHF/6-31G理论水平上，利用一些物理化学和量子化学参数，研究了结构与抗菌活性之间的关系。发现预测的亲脂性参数与抗菌活性之间存在良好的定性相关性。
• Eco-Friendly One-Pot Synthesis of 2,4-Disubstituted Thiazoles by Grinding Under Catalyst- and Solvent-Free Conditions
  作者：Quansehng Ding、Dongjian Zhu、Huile Jin、Jiuxi Chen、Jinchang Ding、Huayue Wu

  DOI：10.1080/10426507.2010.492366

  日期：2011.1.31

  Abstract An efficient and facile synthesis of 2,4-disubstituted thiazoles is achieved by a one-pot reaction of aldehydes and α-bromoketones with thiosemicarbazide by grinding under catalyst- and solvent-free conditions. This method has notable advantages in terms of simple workup, neat conditions, high yield, reasonably rapid reaction rate, and environmental friendliness. Supplemental materials are

  摘要 通过醛和α-溴酮与氨基硫脲的一锅反应，在无催化剂和无溶剂的条件下研磨，实现了2,4-二取代噻唑的高效、简便合成。该方法具有后处理简单、条件整洁、收率高、反应速度合理、环境友好等显着优势。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• An investigation of the biological effect of structural modifications of isothiosemicarbazones and their cyclic analogues
  作者：E Maccioni、M.C Cardia、S Distinto、L Bonsignore、A De Logu

  DOI：10.1016/s0014-827x(03)00154-x

  日期：2003.9

  Several arylideneisothiosemicarbazones and arylidenehydrazothiazoles have been synthesised to obtain new antimicrobial agents. Their activity against both bacteria and fungi has been tested and some interesting informations about their biological activity have been obtained.
• Selective Inhibitory Activity against MAO and Molecular Modeling Studies of 2-Thiazolylhydrazone Derivatives
  作者：Franco Chimenti、Elias Maccioni、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Olivia Befani、Paola Turini、Stefano Alcaro、Francesco Ortuso、Maria C. Cardia、Simona Distinto

  DOI：10.1021/jm060869d

  日期：2007.2.1

  A series of 2-thiazolylhydrazone derivatives have been investigated for the ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) selectively. All of the compounds showed high activity against both the MAO-A and the MAO-B isoforms with pK(i) values ranging between 5.92 and 8.14 for the MAO-A and between 4.69 and 9.09 for the MAO-B isoforms. Both the MAO-A and the MAO-B isoforms, deposited in the Protein Data Bank as model 2BXR and 1GOS, respectively, were considered in a computational study performed with docking techniques on the most active and MAO-B-selective inhibitor, 18.
• Hypervalent Iodine in the Synthesis of Bridgehead Heterocycles: A New Synthesis of 3, 5-Diarylthiazolo[2, 3-C]-s-triazoles
  作者：Om Prakash、Rajesh K. Saini、Devinder Kumar、Shiv P. Singh

  DOI：10.1080/00397919508013857

  日期：1995.11

  The synthesis of 3,5-diarylthiazolo[2,3-c]-s-triazoles (3a-f) has been accomplished by using a new method involving oxidation of arenecarbaldehyde-4-arylthiazol-2-ylhydrazones (2a-f) with iodobenzene diacetate (IBD) in dichloromethane by intramolecular cyclization in high yields.