1-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine | 949912-69-0

• 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-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine
• 英文别名: 4-(4-fluorophenyl)-N-[(3-methylcyclohexylidene)amino]-1,3-thiazol-2-amine
• CAS: 949912-69-0
• 化学式: C₁₆H₁₈FN₃S
• 分子量: 303.403
• InChiKey: NWQWTMZVVHKXDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.28
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine 在 Chiralpak AS-H column 作用下， 生成 (R)-1-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine 、 (S)-1-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine
  参考文献：
  名称：

  Synthesis, Stereochemical Separation, and Biological Evaluation of Selective Inhibitors of Human MAO-B: 1-(4-Arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines

  摘要：

  Novel 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine derivatives have been investigated for their ability to inhibit selectively the activity of the human B isoform of monoamine oxidase. These compounds were obtained as racemates and (R)-enantiomers by a stereoconservative synthetic pattern in high yield and enantiomeric excess. The (S)-enantiomers of the most active derivatives have been separated by enantioselective HPLC. All compounds showed selective activity against hMAO-B with IC(50) ranging between 21.90 and 0.018 mu M.

  DOI：

  10.1021/jm100120s
• 作为产物：
  描述：

  [(3-Methylcyclohexylidene)amino]thiourea 在 α-halo-4-fluoroacetophenone 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 1-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine
  参考文献：
  名称：

  Synthesis, Stereochemical Separation, and Biological Evaluation of Selective Inhibitors of Human MAO-B: 1-(4-Arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines

  摘要：

  Novel 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine derivatives have been investigated for their ability to inhibit selectively the activity of the human B isoform of monoamine oxidase. These compounds were obtained as racemates and (R)-enantiomers by a stereoconservative synthetic pattern in high yield and enantiomeric excess. The (S)-enantiomers of the most active derivatives have been separated by enantioselective HPLC. All compounds showed selective activity against hMAO-B with IC(50) ranging between 21.90 and 0.018 mu M.

  DOI：

  10.1021/jm100120s

文献信息

• Synthesis and in vitro activity of 2-thiazolylhydrazone derivatives compared with the activity of clotrimazole against clinical isolates of Candida spp.
  作者：Franco Chimenti、Bruna Bizzarri、Elias Maccioni、Daniela Secci、Adriana Bolasco、Rossella Fioravanti、Paola Chimenti、Arianna Granese、Simone Carradori、Daniela Rivanera、Daniela Lilli、Alessandra Zicari、Simona Distinto

  DOI：10.1016/j.bmcl.2007.05.078

  日期：2007.8

  In this paper, we report on the synthesis of a novel series of 2-thiazolylhydrazone derivatives and the influence of the substituents on the thiazole ring on antifungal activity. All synthesized compounds were screened for their in vitro activities against 22 clinical isolates of Candida spp., representing six different species, compared to clotrimazole as a reference compound. Some of the tested compounds were found to possess significant antifungal activity when compared to clotrimazole, in particular compound 14 which exhibited higher potency against most of the Candida spp. considered. The compounds that were most active as anti-Candida agents were also Submitted to cytotoxic screening by the Trypan Blue dye exclusion assay and in general they were shown to induce low cytotoxic effects. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, Stereochemical Separation, and Biological Evaluation of Selective Inhibitors of Human MAO-B: 1-(4-Arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazines
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Simone Carradori、Matilde Yáñez、Francisco Orallo、M. Luisa Sanna、Bruno Gallinella、Roberto Cirilli

  DOI：10.1021/jm100120s

  日期：2010.9.9

  Novel 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine derivatives have been investigated for their ability to inhibit selectively the activity of the human B isoform of monoamine oxidase. These compounds were obtained as racemates and (R)-enantiomers by a stereoconservative synthetic pattern in high yield and enantiomeric excess. The (S)-enantiomers of the most active derivatives have been separated by enantioselective HPLC. All compounds showed selective activity against hMAO-B with IC(50) ranging between 21.90 and 0.018 mu M.