1-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(propan-2-ylidene)hydrazine | 324066-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(propan-2-ylidene)hydrazine
• 英文别名: 4-(4-Methoxyphenyl)-2-(2-(propan-2-ylidene)hydrazinyl)thiazole；4-(4-methoxyphenyl)-N-(propan-2-ylideneamino)-1,3-thiazol-2-amine
• CAS: 324066-62-8
• 化学式: C₁₃H₁₅N₃OS
• 分子量: 261.348
• InChiKey: JJROBJWDPANJIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酮 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 1-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(propan-2-ylidene)hydrazine
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel (thiazol-2-yl)hydrazine derivatives as promising anti-Candida agents

  摘要：

  Thirty-eight new (4-(4-substituted-phenyl/2,4-disubstituted-phenyl)-thiazol-2-yl)hydrazine derivatives were synthesized in good yield and assayed for their in vitro anti-Candida activity, compared to topical and systemic antifungal drugs, against twenty-two clinical isolates of Candida spp. The concurrent presence of aliphatic chains or cycloaliphatic rings at N1-hydrazine and a 4-methyl/4-methoxyphenyl at C4 position of the thiazole nucleus exhibited an interesting anti-Candida inhibitory activity. Moreover, some of the most active compounds showed synergistic antifungal effects and lower cell toxicity when combined with clotrimazole. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.042

文献信息

• Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
  作者：Simone Carradori、Dante Rotili、Celeste De Monte、Alessia Lenoci、Melissa D'Ascenzio、Veronica Rodriguez、Patrizia Filetici、Marco Miceli、Angela Nebbioso、Lucia Altucci、Daniela Secci、Antonello Mai

  DOI：10.1016/j.ejmech.2014.04.042

  日期：2014.6

  thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis

  最近，我们描述了一些（噻唑-2-基）azo作为抗原生动物，抗真菌和抗MAO试剂以及Gcn5 HAT抑制剂。在这些最后的化合物中，CPTH2和CPTH6在细胞中显示出HAT抑制作用和广泛的抗癌特性。为了鉴定比两个原型更有效的HAT抑制剂，我们合成了几种新的（噻唑-2-基）azo酮，包括一些相关的噻唑烷和嘧啶4（3 H）-酮，并测试了我们现有的整个文库针对人p300和PCAF HAT酶的实验室。某些化合物（1x，1c '，1d '，1i '和2m）在抑制p300 HAT酶方面比CPTH2和CPTH6更有效。在人白血病U937和结肠癌HCT116细胞（100μM，30小时）中进行测试时，1x，1i '和2m产生的凋亡（U937细胞）或类似细胞（HCT116细胞）高于CPTH6，并且在诱导细胞分化方面比CPTH6更有效（U937细胞）。
• Microwave and Ultrasound-Assisted Synthesis of Thiosemicarbazones and Their Corresponding (4,5-Substituted-thiazol-2-yl)hydrazines
  作者：Simone Carradori、Daniela Secci、Melissa D'Ascenzio、Paola Chimenti、Adriana Bolasco

  DOI：10.1002/jhet.1856

  日期：2014.11

  Hantzsch cyclization of thiosemicarbazone intermediates is a very popular approach to the synthesis of substituted thiazoles. We developed a convenient microwave and ultrasound‐assisted method both for the synthesis of 1‐(alkyliden/cycloalkyliden/aryliden)thiosemicarbazone intermediates and their cyclization into (4,5‐substituted‐thiazol‐2‐yl)hydrazines. The search for optimal reaction conditions included

  硫半脲中间体的汉茨环化是合成取代噻唑的一种非常流行的方法。我们开发了一种便捷的微波和超声辅助方法，用于合成1-（亚烷基/环亚烷基/芳基）硫代半碳酮中间体并将其环化为（4,5-取代-噻唑-2-基）肼。寻找最佳反应条件的方法包括在不连续的温度，压力和照射功率下使用不同的催化剂（路易斯酸和树脂）和溶剂。比较收率，反应时间和工作量证明，微波和超声辅助技术优于常规加热，并且对合成有显着影响。
• 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 and cytotoxicity of novel (thiazol-2-yl)hydrazine derivatives as promising anti-Candida agents
  作者：Simone Carradori、Daniela Secci、Adriana Bolasco、Daniela Rivanera、Emanuela Mari、Alessandra Zicari、Lavinia Vittoria Lotti、Bruna Bizzarri

  DOI：10.1016/j.ejmech.2013.04.042

  日期：2013.7

  Thirty-eight new (4-(4-substituted-phenyl/2,4-disubstituted-phenyl)-thiazol-2-yl)hydrazine derivatives were synthesized in good yield and assayed for their in vitro anti-Candida activity, compared to topical and systemic antifungal drugs, against twenty-two clinical isolates of Candida spp. The concurrent presence of aliphatic chains or cycloaliphatic rings at N1-hydrazine and a 4-methyl/4-methoxyphenyl at C4 position of the thiazole nucleus exhibited an interesting anti-Candida inhibitory activity. Moreover, some of the most active compounds showed synergistic antifungal effects and lower cell toxicity when combined with clotrimazole. (C) 2013 Elsevier Masson SAS. All rights reserved.