N,N-dimethyl-4-{[2-(4-phenyl-1,3-thiazol-2-yl)hydrazinylidene]methyl}aniline | 21938-32-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-{[2-(4-phenyl-1,3-thiazol-2-yl)hydrazinylidene]methyl}aniline
• 英文别名: 2-(2-(4-N,N-dimethylbenzylidene)hydrazinyl)-4-phenylthiazole；N-[[4-(dimethylamino)phenyl]methylideneamino]-4-phenyl-1,3-thiazol-2-amine
• CAS: 21938-32-9
• 化学式: C₁₈H₁₈N₄S
• mdl: MFCD00501359
• 分子量: 322.434
• InChiKey: ILWHJUUMBODAQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 以 乙醇 、 水 为溶剂， 生成 N,N-dimethyl-4-{[2-(4-phenyl-1,3-thiazol-2-yl)hydrazinylidene]methyl}aniline
  参考文献：
  名称：

  Synthesis, Antibacterial Activity and Quantum-Chemical Studies of Novel 2-Arylidenehydrazinyl-4-arylthiazole Analogues

  摘要：

  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。

  DOI：

  10.1248/cpb.59.568

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。
• 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。
• Thiazole compounds with activity against Cryptococcus gattii and Cryptococcus neoformans in vitro
  作者：Nívea Pereira de Sá、Cleudiomar Inácio Lino、Nayara Cristina Fonseca、Beatriz Martins Borelli、Jonas Pereira Ramos、Elaine Maria Souza-Fagundes、Carlos Augusto Rosa、Daniel Assis Santos、Renata Barbosa de Oliveira、Susana Johann

  DOI：10.1016/j.ejmech.2015.07.032

  日期：2015.9

  Human cryptococcosis can occur as a primary or opportunistic infection and develop as an acute, subacute, or chronic, systemic infection involving different host organs. We evaluated the antifungal activity of thirteen compounds against Cryptococcus gattii and Cryptococcus neoformans in vitro, by assessing the toxicity of the compounds showing the greatest antifungal activity in VERO cells and murine macrophages. From these results, four compounds were considered promising for further studies because they displayed low cytotoxicity and significant antifungal activity. The heterocyclic compounds 1b, 1c, 1d, and 1m have antifungal activity levels between that of amphotericin B and fluconazole in vitro. The death curve of Cryptococcus spp. treated with these four compounds was similar to the curve obtained for amphotericin B, in that we observed a significant reduction in cell viability within the first 24 h of treatment. Additionally, we found that there was no effect when these compounds were combined with amphotericin and fluconazole, except for 1c, which antagonized the effect of amphotericin B against C. gattii, also reflected in the reduction of the post-antifungal effect (PAFE); however, this interaction did not alter the ergosterol content. The results shown in this paper reveal the discovery of novel thiazole compounds, which are easy to synthesize, and with potentially exhibit antifungal activity, and display low cytotoxicity in normal mammalian cells. These compounds can be used as prototypes for the design of new antifungal drugs against C gattii and C neoformans. (C) 2015 Elsevier Masson SAS. All rights reserved.