1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(2-methylcyclohexylidene)hydrazine | 1242658-38-3

• 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-(3-methoxyphenyl)thiazol-2-yl)-2-(2-methylcyclohexylidene)hydrazine
• 英文别名: 4-(3-methoxyphenyl)-N-[(2-methylcyclohexylidene)amino]-1,3-thiazol-2-amine
• CAS: 1242658-38-3
• 化学式: C₁₇H₂₁N₃OS
• 分子量: 315.439
• InChiKey: TXFHMWOTRVTEOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  2-溴-3‘-甲氧基苯乙酮 、 2-methylcyclohexanone thiosemicarbazone 以 乙醇 为溶剂， 反应 4.0h， 生成 1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(2-methylcyclohexylidene)hydrazine
  参考文献：
  名称：

  Investigations on the 2-thiazolylhydrazyne scaffold: Synthesis and molecular modeling of selective human monoamine oxidase inhibitors

  摘要：

  A new series of [4-(3-methoxyphenyl)-thiazol-2-yl]hydrazyne derivatives were synthesized in good yield (71-99%) and characterized by elemental analysis and H-1 NMR studies. The compounds were assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity and most of them showed IC50 values in the nanomolar range, thus demonstrating our interest in this privileged scaffold. The most active and selective derivative (20), bearing a pyridine moiety on the C=N, displayed IC50 = 3.81 +/- 0.12 nM and selectivity ratio = 119 toward hMAO-B. Molecular modeling studies were carried out on recent and high resolution hMAO-A and hMAO-B crystallographic structures to better justify the enzyme-inhibitor interaction toward hMAO isoforms and to explain the structure-activity relationship of this kind of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.007

文献信息

• Investigations on the 2-thiazolylhydrazyne scaffold: Synthesis and molecular modeling of selective human monoamine oxidase inhibitors
  作者：Franco Chimenti、Adriana Bolasco、Daniela Secci、Paola Chimenti、Arianna Granese、Simone Carradori、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.bmc.2010.06.007

  日期：2010.8

  A new series of [4-(3-methoxyphenyl)-thiazol-2-yl]hydrazyne derivatives were synthesized in good yield (71-99%) and characterized by elemental analysis and H-1 NMR studies. The compounds were assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity and most of them showed IC50 values in the nanomolar range, thus demonstrating our interest in this privileged scaffold. The most active and selective derivative (20), bearing a pyridine moiety on the C=N, displayed IC50 = 3.81 +/- 0.12 nM and selectivity ratio = 119 toward hMAO-B. Molecular modeling studies were carried out on recent and high resolution hMAO-A and hMAO-B crystallographic structures to better justify the enzyme-inhibitor interaction toward hMAO isoforms and to explain the structure-activity relationship of this kind of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.