1-(4-(2-Cyclopentylideneethyl)cyclopenta-1,4-dienyl)-2,4-dimethylbenzene | 1245711-04-9

• 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-(4-(2-Cyclopentylideneethyl)cyclopenta-1,4-dienyl)-2,4-dimethylbenzene
• 英文别名: N-(cyclopentylideneamino)-4-(2,4-difluorophenyl)-1,3-thiazol-2-amine
• CAS: 1245711-04-9
• 化学式: C₁₄H₁₃F₂N₃S
• 分子量: 293.34
• InChiKey: JSAGSTLNHOZIBR-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  421.4±53.0 °C(predicted)
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-环戊基亚基硫代氨基甲酰肼 、 2-溴-2',4'-二氟苯乙酮 以 乙醇 为溶剂， 生成 1-(4-(2-Cyclopentylideneethyl)cyclopenta-1,4-dienyl)-2,4-dimethylbenzene
  参考文献：
  名称：

  Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors

  摘要：

  The present study reports on synthesis in high yields (70-99%), HPLC enantioseparation, inhibitory activity against human monoamino oxidases, and molecular modeling including 3D-QSAR studies, of a large series of (4-aryl-thiazol-2-yl) hydrazones (1-45). Most of the synthesized compounds proved to be potent and selective inhibitors of hMAO-B isoform in the micromolar or nanomolar range, thus demonstrating that hydrazothiazole could be considered a good pharmacophore to design new hMAO-B inhibitors. Due to the presence in some derivatives of a chiral center, we also performed a semipreparative chromatographic enantioseparation of these compounds obtained by a stereoconservative pattern. The separated enantiomers were submitted to in vitro biological evaluation to point out the stereorecognition of the active site of the enzyme towards these structures. Finally, a 3D-QSAR study was carried out using Comparative Molecular Field Analysis (CoMFA), aiming to deduce rational guidelines for the further structural modification of these lead compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.070

文献信息

• Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Simone Carradori、Elias Maccioni、M. Cristina Cardia、Matilde Yáñez、Francisco Orallo、Stefano Alcaro、Francesco Ortuso、Roberto Cirilli、Rosella Ferretti、Simona Distinto、Johannes Kirchmair、Thierry Langer

  DOI：10.1016/j.bmc.2010.05.070

  日期：2010.7

  The present study reports on synthesis in high yields (70-99%), HPLC enantioseparation, inhibitory activity against human monoamino oxidases, and molecular modeling including 3D-QSAR studies, of a large series of (4-aryl-thiazol-2-yl) hydrazones (1-45). Most of the synthesized compounds proved to be potent and selective inhibitors of hMAO-B isoform in the micromolar or nanomolar range, thus demonstrating that hydrazothiazole could be considered a good pharmacophore to design new hMAO-B inhibitors. Due to the presence in some derivatives of a chiral center, we also performed a semipreparative chromatographic enantioseparation of these compounds obtained by a stereoconservative pattern. The separated enantiomers were submitted to in vitro biological evaluation to point out the stereorecognition of the active site of the enzyme towards these structures. Finally, a 3D-QSAR study was carried out using Comparative Molecular Field Analysis (CoMFA), aiming to deduce rational guidelines for the further structural modification of these lead compounds. (C) 2010 Elsevier Ltd. All rights reserved.