(E)-N-(4-phenylthiazol-2-yl)cinnamamide | 1107621-03-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-(4-phenylthiazol-2-yl)cinnamamide
• 英文别名: 2-Cinnamamido-4-phenylthiazole；(E)-3-phenyl-N-(4-phenyl-1,3-thiazol-2-yl)prop-2-enamide
• CAS: 1107621-03-3
• 化学式: C₁₈H₁₄N₂OS
• 分子量: 306.388
• InChiKey: WOJRHCOBUKJCAJ-VAWYXSNFSA-N

物化性质

• 熔点：
  238-239 °C(Solv: ethanol (64-17-5))
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 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：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-(4-phenylthiazol-2-yl)cinnamamide 在 四氯苯醌 、 sodium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 为溶剂， 生成 3'-(4-phenylthiazol-2-ylamino)-5'-phenyl-1'H-pyrazole-1'-carbothioamide
  参考文献：
  名称：

  Synthesis and antimicrobial activity of amine linked bis- and tris-heterocycles

  摘要：

  A series of amine linked bis- and tris-heterocycles were prepared from heteroaryl cinnamamides and tested for antimicrobial activity. The compounds 11c and 12c exhibited excellent antibacterial activity while 12a and 12c displayed excellent antifungal activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.001
• 作为产物：
  描述：

  2-氨基-4-苯基噻唑 、 肉桂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以59%的产率得到(E)-N-(4-phenylthiazol-2-yl)cinnamamide
  参考文献：
  名称：

  Design, Synthesis, and Cytoprotective Effect of 2-Aminothiazole Analogues as Potent Poly(ADP-Ribose) Polymerase-1 Inhibitors

  摘要：

  A series of novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors were designed within 2-aminothiazole analogues (4-10) based on a constructed three-dimensional pharmacophore model. After synthesis, the inhibitory effect on PARP-1 activity and the cytoprotective action of these compounds were tested and evaluated. Among them, compounds 4-6 and 10 appeared to be potent PARP-1 inhibitors with IC50 values less than 1 mu M, which had been perfectly predicted by pharmacophore model. These compounds proved to be highly potent against cell injury induced by H2O2 and oxygen-glucose deprivation (OGD) in PC12 cells. These novel 2-aminothiazole analogues are potentially applicable as neuroprotective agents for the treatment of neurological diseases.

  DOI：

  10.1021/jm800902t

文献信息

• Synthesis and antimicrobial activity of amido linked pyrrolyl and pyrazolyl-oxazoles, thiazoles and imidazoles
  作者：V. Padmavathi、C. Prema kumari、B.C. Venkatesh、A. Padmaja

  DOI：10.1016/j.ejmech.2011.08.032

  日期：2011.11

  A new class of amido linked bis heterocycles viz., pyrrolyl/pyrazolyl-oxazoles, thiazoles and imidazoles were prepared by 1,3-dipolar cycloaddition of TosMIC and diazomethane to the respective cinnamamide derivatives and screened for antimicrobial activity. The chlorosubstituted imidazolyl cinnamamide (6c) is the most potential antimicrobial agent as it displayed strong antibacterial activity against Bacillus subtilis and antifungal activity against Penicillium chrysogenum. (C) 2011 Elsevier Masson SAS. All rights reserved.
• HUSAIN I.; MISRA S. N., J. INDIAN CHEM. SOC., 1979, 56, NO 9, 917-918
  作者：HUSAIN I.、 MISRA S. N.

  DOI：——

  日期：——
• TELLY V. YU.; LI A. L., SB. NAUCH. TR. TASHKENT. YH-T, 1980, HO 622, 7-9
  作者：TELLY V. YU.、 LI A. L.

  DOI：——

  日期：——
• Synthesis and antimicrobial activity of amine linked bis- and tris-heterocycles
  作者：T. Bhanu Prakash、G. Dinneswara Reddy、A. Padmaja、V. Padmavathi

  DOI：10.1016/j.ejmech.2014.06.001

  日期：2014.7

  A series of amine linked bis- and tris-heterocycles were prepared from heteroaryl cinnamamides and tested for antimicrobial activity. The compounds 11c and 12c exhibited excellent antibacterial activity while 12a and 12c displayed excellent antifungal activity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Design, Synthesis, and Cytoprotective Effect of 2-Aminothiazole Analogues as Potent Poly(ADP-Ribose) Polymerase-1 Inhibitors
  作者：Wen-Ting Zhang、Jin-Lan Ruan、Peng-Fei Wu、Feng-Chao Jiang、Li−Na Zhang、Wei Fang、Xiang-Long Chen、Yue Wang、Bao-Shuai Cao、Gang-Ying Chen、Yi-Jing Zhu、Jun Gu、Jian-Guo Chen

  DOI：10.1021/jm800902t

  日期：2009.2.12

  A series of novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors were designed within 2-aminothiazole analogues (4-10) based on a constructed three-dimensional pharmacophore model. After synthesis, the inhibitory effect on PARP-1 activity and the cytoprotective action of these compounds were tested and evaluated. Among them, compounds 4-6 and 10 appeared to be potent PARP-1 inhibitors with IC50 values less than 1 mu M, which had been perfectly predicted by pharmacophore model. These compounds proved to be highly potent against cell injury induced by H2O2 and oxygen-glucose deprivation (OGD) in PC12 cells. These novel 2-aminothiazole analogues are potentially applicable as neuroprotective agents for the treatment of neurological diseases.