2-(2-cyclohexylidenehydrazinyl)-4-phenyl-1,3-thiazole | 357639-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-cyclohexylidenehydrazinyl)-4-phenyl-1,3-thiazole
• 英文别名: 2-(2-cyclohexylidenehydrazinyl)-4-phenylthiazole；N-(cyclohexylideneamino)-4-phenyl-1,3-thiazol-2-amine
• CAS: 357639-73-7
• 化学式: C₁₅H₁₇N₃S
• 分子量: 271.386
• InChiKey: RQMWJSWLKXHIEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  449.0±38.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基安替比林 、 2-(2-cyclohexylidenehydrazinyl)-4-phenyl-1,3-thiazole 在 盐酸 、 sodium nitrite 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以73%的产率得到N-(cyclohexylidene)-N'-(5-antipyrinylazo-4-phenylthiazol-2-yl)hydrazine
  参考文献：
  名称：

  Substituted 5-Antipyrinylazo-4-phenyl-2-aminothiazoles as Disperse Dyes for Dyeing Polyester Fabrics

  摘要：

  A series of some new substituted 5-antipyrinylazo4-phenyl-2-aminothiazole disperse dyes was synthesized by diazocoupling of 4-antipyrinyldiazonium chloride with aminothiazole derivatives. The synthesized dyes were characterized by UV-Vis absorption, IR, H-1 NMR, and MS spectroscopy. The dyes gave orange to reddish-violet shades with very good depth and levelness when applied to polyester fabrics as disperse dyes and their fastness properties were evaluated on polyester fibers. Also the position of color in CIELAB coordinates ( L*, a*, b*, H*, and C*) was assessed.

  DOI：

  10.1007/s00706-007-0749-4
• 作为产物：
  描述：

  (环己亚基氨基)硫脲 、 alpha-氯乙酰苯 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到2-(2-cyclohexylidenehydrazinyl)-4-phenyl-1,3-thiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 1-indanone thiazolylhydrazone derivatives as anti-Trypanosoma cruzi agents

  摘要：

  A series of novel 4-arylthiazolylhydrazones (TZHs) derived from 1-indanones were synthesized in good yields (66-92%) in a simple procedure using microwave irradiation and then characterized by spectroscopy studies. The compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against the epimastigote, trypomastigote and amastigote forms of the parasite. Most TZHs displayed excellent activity, and were more potent and selective than the reference drug Benznidazole, used in the current chemotherapy. Analysis of the free sterols from parasite incubated with the compounds showed that inhibition of ergosterol biosynthesis is a possible target for the action of these new TZHs. In particular, TZH 9 emerged as a promising antichagasic compound to be evaluated in animal models. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.013

文献信息

• Efficient one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones in water under ultrasound irradiation
  作者：Dong-Nuan Zhang、Ji-Tai Li、Ya-Li Song、Hui-Min Liu、Hong-Ya Li

  DOI：10.1016/j.ultsonch.2011.10.017

  日期：2012.5

  A highly efficient and facile one-pot three-component synthesis of N-(4-arylthiazol-2-yl) hydrazones was carried out in excellent yield without any catalyst in water under ultrasound irradiation.

  N-（4-芳基噻唑-2-基）hydr的高效，便捷的一锅三组分合成法在超声波照射下在水中无催化剂的情况下以优异的收率进行。
• Selective Inhibitory Activity against MAO and Molecular Modeling Studies of 2-Thiazolylhydrazone Derivatives
  作者：Franco Chimenti、Elias Maccioni、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Olivia Befani、Paola Turini、Stefano Alcaro、Francesco Ortuso、Maria C. Cardia、Simona Distinto

  DOI：10.1021/jm060869d

  日期：2007.2.1

  A series of 2-thiazolylhydrazone derivatives have been investigated for the ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) selectively. All of the compounds showed high activity against both the MAO-A and the MAO-B isoforms with pK(i) values ranging between 5.92 and 8.14 for the MAO-A and between 4.69 and 9.09 for the MAO-B isoforms. Both the MAO-A and the MAO-B isoforms, deposited in the Protein Data Bank as model 2BXR and 1GOS, respectively, were considered in a computational study performed with docking techniques on the most active and MAO-B-selective inhibitor, 18.
• Synthesis and anti-microbial activity of isothiosemicarbazones and cyclic analogues
  作者：E Maccioni、M.C Cardia、L Bonsignore、A Plumitallo、M.L Pellerano、A De Logu

  DOI：10.1016/s0014-827x(02)01288-0

  日期：2002.9

  It is known that some derivatives of both thiourea and thiosemicarbazide exhibit potent anti-microbial activity. In order to investigate the effects on the biological properties of structural modifications of such structures, we have synthesised and studied some arylidenisothiosenticarbazones. In this paper we report on the synthesis and structure-activity relationships of some isothiosemicarbazones, where the arylidene group has been replaced with a cycloalkyl group and the sulfur atom has been either differently substituted or enclosed in a thiazole ring. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• [EN] MONOAMINE OXIDASE B BINDERS FOR USE IN THE TREATMENT AND THE DIAGNOSTIC OF ALZHEIMER DISEASE<br/>[FR] LIANTS DE TYPE MONOAMINE OXYDASE B POUR LEUR UTILISATION DANS LE TRAITEMENT ET LE DIAGNOSTIC DE LA MALADIE D'ALZHEIMER
  申请人：CLINO LTD

  公开号：WO2017103257A1

  公开（公告）日：2017-06-22

  The present invention provides methods useful in the management neuropathological conditions where expression of monoamine oxidase B (MAO-B) deviates from that seen in healthy subjects. The invention provides for the use of compounds in therapeutic and diagnostic applications.