1-benzylidene-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazine | 306280-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzylidene-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazine
• 英文别名: Benzaldehyde 2-[4-(4-chlorophenyl)-2-thiazolyl]hydrazone；N-(benzylideneamino)-4-(4-chlorophenyl)-1,3-thiazol-2-amine
• CAS: 306280-32-0
• 化学式: C₁₆H₁₂ClN₃S
• 分子量: 313.81
• InChiKey: FPHQYBHFAYWQOC-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  488.1±37.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-benzylidene-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazine 在 poly[(4-diacetoxyiodo)-styrene] 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以65%的产率得到3-phenyl-5-p-chlorophenyl-thiazolo[2,3-c]-s-triazole
  参考文献：
  名称：

  Synthesis of Thiazolo[2,3‐c]‐s‐triazoles Using Poly[(4‐diacetoxyiodo)styrene]

  摘要：

  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.

  DOI：

  10.1081/scc-200063923
• 作为产物：
  描述：

  苯甲醛 在 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-benzylidene-2-(4-(4-chlorophenyl)thiazol-2-yl)hydrazine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of some novel benzylidene-2-(4-phenylthiazol-2-yl) hydrazines as potential anti-inflammatory agents

  摘要：

  A series of substituted benzylidene-2-(4-phenylthiazol-2-yl) hydrazines (2a-q) have been synthesized, characterized and evaluated for their anti-inflammatory activity by carrageenin-induced hind paw edema (acute inflammation) and cotton pellet granuloma (chronic inflammation) methods in rats. In carrageenin-induced hind paw edema method, compounds 2a, 2b, 2c, 2d, 2h, 2k and 2p at a dose of 20 mg kg(-1) body weight, p.o. showed excellent inhibitions (51.80-86.74 %) in between 1 and 4 h. Similarly, in cotton pellet granuloma method, compounds 2a, 2b, 2c, 2d, 2h, 2k and 2p at a dose of 20 mg kg(-1) body weight, p.o. inhibited the granuloma formation (71.71-90.19 % inhibition) which was comparable to that of standard drug, ibuprofen (90.36 % inhibition of paw volume at 3 h and 94.02 % inhibition of granuloma formation). Structure activity relationship studies showed excellent activity of the compounds containing electron withdrawing group (fluoro, chloro, bromo or nitro) in phenyl ring at C2 and/or C4 position of thiazole ring.

  DOI：

  10.1007/s00044-013-0708-z

文献信息

• 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
• 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.