N-[(2-methylcyclohexylidene)amino]-4-(4-methylphenyl)-1,3-thiazol-2-amine | 949912-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[(2-methylcyclohexylidene)amino]-4-(4-methylphenyl)-1,3-thiazol-2-amine
• CAS: 949912-60-1
• 化学式: C₁₇H₂₁N₃S
• 分子量: 299.44
• InChiKey: OPFWPVHEWFRTHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  0.41
• 拓扑面积：
  37.28
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-溴-4'-甲基苯乙酮 、 2-methylcyclohexanone thiosemicarbazone 以 异丙醇 为溶剂， 反应 2.0h， 以93%的产率得到N-[(2-methylcyclohexylidene)amino]-4-(4-methylphenyl)-1,3-thiazol-2-amine
  参考文献：
  名称：

  Synthesis, Stereochemical Identification, and Selective Inhibitory Activity against Human Monoamine Oxidase-B of 2-Methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones

  摘要：

  A series of 2-methylcyclohexylidene-(4-arylthiazol-2-yl)hydrazones have been investigated for their ability to inhibit selectively the activity of the human A and B isoforms of monoamine oxidase (MAO). The target compounds, which present a stereogenic center on the cyclohexane ring, were obtained as pure (R) and (S) enantiomers by enantioselective HPLC. The absolute configuration of homochiral forms isolated on a semipreparative scale was obtained by a combined strategy based on chemical correlation and single-crystal X-ray diffraction. All compounds showed higher activity against the human MAO-B isoform with IC(50) values ranging between 26.81 +/- 2.74 mu M and 14.20 +/- 0.26 nM, and the assays carried out on the pure enantiomers showed higher activity for the (R) form. A computational study was performed by molecular mechanics, DFT-based quantomechanics, and docking techniques on the most active and human MAO-B selective inhibitor 8.

  DOI：

  10.1021/jm800132g

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.