1-(4-methoxybenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine

• 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-methoxybenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine
• 英文别名: 2-(2-(4-methoxybenzylidene)hydrazinyl)-4-(4-chlorophenyl)thiazole；4-(4-chlorophenyl)-N-[(4-methoxyphenyl)methylideneamino]-1,3-thiazol-2-amine
• 化学式: C₁₇H₁₄ClN₃OS
• 分子量: 343.837
• InChiKey: AALRMFYQWJBGLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以74%的产率得到5-(4-Chlorophenyl)-3-(4-methoxyphenyl)-[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：

  2-phenoxy-4-(4-chlorophenyl)thiazole 在 溶剂黄146 、 肼 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 1-(4-methoxybenzylidene)-2-[4-(4-chlorophenyl)thiazol-2-yl]hydrazine
  参考文献：
  名称：

  2,4- 和 2,5-二取代芳基噻唑：通过 CH 偶联和生物学评价快速合成

  摘要：

  由对常见抗生素产生耐药性的细菌引起的危及生命的感染，例如耐甲氧西林金黄色葡萄球菌 (MRSA)，已成为世界各地医院和其他地区的严重问题。因此，开发针对这些细菌的有效抗生素类别是一个紧迫的课题。在此，我们报告了一系列利用 C-H 偶联方法的 2-亚芳基肼基-4-芳基噻唑和 2-亚芳基肼基-5-芳基噻唑类似物的逐步经济和面向多样性的合成。合成了一个包含 54 个新同源物的文库，并测试了它们的生物学潜力。此外，还收集了有关这些杂二芳基化合物的构效关系 (SAR) 的新知识。

  DOI：

  10.1002/ejoc.201402129

文献信息

• Synthesis, anti-HIV activity, molecular modeling study and QSAR of new designed 2-(2-arylidenehydrazinyl)-4-arylthiazoles
  作者：Amna Rauf、Muhammad K. Kashif、Bahjat A. Saeed、Najim A. Al-Masoudi、Shahid Hameed

  DOI：10.1016/j.molstruc.2019.07.113

  日期：2019.12

  Abstract Taking into consideration the eminence of 1,3-thiazoles in medicinal chemistry and in a view of procuring more pronounced biological contour, the synthesis of 2-(2-arylidenehydrazinyl)-4-arylthiazoles 6–43 was made possible by the cyclization reaction of thiosemicarbazones and α-bromoacetophenones. The thiosemicarbazones 5a-m were in turn synthesized from substituted benzaldehydes or acetophenones

  摘要 考虑到 1,3-噻唑类化合物在药物化学方面的优势，为了获得更显着的生物轮廓，通过环化反应合成 2-(2-亚芳基肼基)-4-芳基噻唑类化合物 6-43 成为可能。缩氨基硫脲和 α-溴苯乙酮。缩氨基硫脲 5a-m 依次由取代的苯甲醛或苯乙酮和缩氨基硫脲合成。进行反应条件的优化以得到良好产率的目标分子。使用 MTT 测定法在体外评估了所有新化合物对 MT4 细胞中 HIV-1 和 HIV-2 复制的抗病毒活性。筛选结果表明，化合物 32-34 是该系列中唯一抑制细胞培养物中 HIV-1 和 HIV-2 复制的化合物，IC50 > 2.71，分别 >2.19 和 >1.71 μM。还研究了化合物 32 和 34 与人类免疫缺陷病毒逆转录酶 (HIV RT) 的一些氨基酸的分子对接。通过多元线性回归（MRL）和遗传函数逼近（GFA）两种方法获得了新合成的同类物之间的初步量子构效关系（QSAR）。
• Design, synthesis and biological evaluation of novel thiazole derivatives as potent FabH inhibitors
  作者：Peng-Cheng Lv、Kai-Rui Wang、Ying Yang、Wen-Jun Mao、Jin Chen、Jing Xiong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2009.09.111

  日期：2009.12

  Fatty acid biosynthesis is essential for bacterial survival. Components of this biosynthetic pathway have been identified as attractive targets for the development of new antibacterial agents. FabH, beta-ketoacylacyl carrier protein (ACP) synthase III, is a particularly attractive target, since it is central to the initiation of fatty acid biosynthesis and is highly conserved among Gram positive and negative bacteria. Three series of Schiff bases containing thiazole template were synthesized and developed as potent inhibitors of FabH. This inhibitor class demonstrates strong antibacterial activity. Escherichia coli FabH inhibitory assay and docking simulation indicated that the compounds 11 and 18 were potent inhibitors of E. coli FabH. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and biological assessment of novel 2-thiazolylhydrazones and computational analysis of their recognition by monoamine oxidase B
  作者：Simona Distinto、Matilde Yáñez、Stefano Alcaro、M. Cristina Cardia、Marco Gaspari、M. Luisa Sanna、Rita Meleddu、Francesco Ortuso、Johannes Kirchmair、Patrick Markt、Adriana Bolasco、Gerhard Wolber、Daniela Secci、Elias Maccioni

  DOI：10.1016/j.ejmech.2011.12.027

  日期：2012.2

  Monoamine oxidase B (MAO-B) is a promising target for the treatment of neurodegenerative disorders. We report the synthesis and the biological evaluation of halogenated derivatives of 1-aryliden-2-(4-phenylthiazol-2-yl)hydrazines. The fluorinated series shows interesting activity and great selectivity toward the human recombinant MAO-B isoform expressed in baculovirus infected BTI insect cells. The multiple crystal structures alignment of the enzyme highlighted pronounced induced fit (IF) adaptations with respect to bound ligands. Therefore, IF docking (IFD) experiments and molecular dynamic (MD) simulations were carried out to reveal the putative binding mode and to explain the experimentally observed differences in the activity of 1-(aryliden-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazines. The importance of water molecules within the binding site was also investigated. These are known to play an important role in the binding site cavity and to mediate protein ligand interactions. Detailed analyses of the trajectories provide insights on the chemical features required for the activity of this scaffold. In particular it was highlighted the importance of fluorine atom interacting with the water close to the cofactor and the influence of steric bulkiness of substituents in the arylidene moiety. Free energy perturbation (FEP) analysis confirmed experimental data. The information we deduced will help to develop novel high-affinity MAO-B inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 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.
• Synthesis of Thiazolo[2,3‐c]‐s‐triazoles Using Poly[(4‐diacetoxyiodo)styrene]
  作者：Shi‐juan Liu、Ji‐zhen Zhang、Guan‐rong Tian、Ping Liu

  DOI：10.1081/scc-200063923

  日期：2005.7

  Arenecarbaldehyde-4-arylthiazol-2-ylhydrazones underwent ring closure with poly[(4-diacetoxyiodo) styrene] (PSDIB) to 3,5-diarylthiazolo[2,3-c]-s-triazoles in dichloromethane.