5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol | 1225196-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-phenyl-3-(4-propan-2-yl-1,3-thiazol-2-yl)-1H-1,2,4-triazole-5-thione
• CAS: 1225196-52-0
• 化学式: C₁₄H₁₄N₄S₂
• 分子量: 302.424
• InChiKey: SAFUTMRAIHMVHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol 在 一水合肼 、 溶剂黄146 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 3-(4-isopropyl thiazol-2-yl)-4-phenyl-5-((5-phenyl-1,3,4-oxadiazol-2-yl) methylthio)-4H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of novel 4-isopropylthiazole-4-phenyl-1,2,4-triazole derivatives as potential antimicrobial and antitubercular agents

  摘要：

  A series of novel 4-isopropylthiazol-4-phenyl-1,2,4-triazol derivatives, N'-(substituted benzylidene)-2-(5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)acetohydrazides 4a-e, 4-isopropylthiazol-2-yl-4'-phenyl-4'H-1', 2',4'-triazol-3'-ylthio (substituted methyl benzylidene) acetohydrazides 5a-f, 3-(4-isopropylthiazol-2-yl)-4-phenyl-5-(5-substituted-1,3,4-oxadiazol-2-ylthio)-4H-1,2,4-triazole derivatives 6a-f and N-acetyl-5'-(4-isopropylthiazol-2-yl)-4'-phenyl-4'H-1,2,4-triazol-3'-ylthio) acetohydrazide 7 were synthesized and characterized by spectroscopy, elemental, and mass spectral analysis. These compounds were evaluated for their preliminary in vitro antibacterial, antifungal, and antitubercular activity against Mycobacterium tuberculosis (M. tuberculosis) H37Rv strain by broth dilution assay method. All the compounds exhibited moderate to significant antibacterial and antifungal activities. Results of the antitubercular screening against Mycobacterium tuberculosis H37Rv showed that compounds 4c and 6c exhibited good antitubercular activity when compared with first line drug isoniazid.

  DOI：

  10.1007/s00044-012-0092-0
• 作为产物：
  描述：

  4-isopropyl-1,3-thiazole-2-carbohydrazide 、 硫代异氰酸苯酯 以 乙醇 为溶剂， 生成 5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  一些新型的以4-异丙基噻唑为基的磺酰基衍生物的合成和药理学评价为有效的抗微生物剂和抗结核剂

  摘要：

  一系列新颖的磺酰基衍生物3-（取代的苄基磺酰基）-5-（4-异丙基噻唑-2-基）-4-苯基-4H-1,2,4-三唑4a – 4e，异丙基噻唑衍生的席夫碱8a –合成了8l和2-（取代的苄基磺酰基）-5-（4-异丙基噻唑-2-基）-1,3,4-恶二唑11a - 11e并通过IR，1 H NMR，13 C NMR，元素和质谱分析。所有化合物均表现出中度至重要的抗菌和抗真菌活性。抗结核分枝杆菌H37Rv的抗结核筛选结果可确定化合物4e，8b，与一线药物异烟肼（0.25μg/ mL）相比，8f是出色的抗结核分子。

  DOI：

  10.1007/s00044-012-0431-1

文献信息

• Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents
  作者：G.V. Suresh Kumar、Y. Rajendraprasad、B.P. Mallikarjuna、S.M. Chandrashekar、C. Kistayya

  DOI：10.1016/j.ejmech.2010.01.045

  日期：2010.5

  In the present study a series of 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazole derivatives have been synthesized and characterized by IR, (1)H NMR, (13)C NMR and mass spectral analysis. Synthesized compounds were evaluated for their preliminary cytotoxicity, antimicrobial and antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth dilution assay method.Antimycobacterial activity tested against M. tuberculosis indicated that compounds 4b and 6g exhibited twofold enhanced potency than parent compound 1 and the results indicate that some of them exhibited promising activities and they deserve more consideration as potential antitubercular agents.Compound 3c, 4b and 6c exhibited good or moderate antibacterial inhibition and compounds 3h and 7c showed excellent antifungal activity. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and pharmacological evaluation of some novel 4-isopropyl thiazole-based sulfonyl derivatives as potent antimicrobial and antitubercular agents
  作者：G. V. Suresh Kumar、Y. Rajendra Prasad、S. M. Chandrashekar

  DOI：10.1007/s00044-012-0431-1

  日期：2013.9

  A series of novel sulfonyl derivatives 3-(substituted benzylsulfonyl)-5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazoles 4a–4e, isopropyl thiazole-derived schiff bases 8a–8l, and 2-(substituted benzylsulfonyl)-5-(4-isopropylthiazol-2-yl)-1,3,4-oxadiazoles 11a–11e were synthesized and characterized by IR, 1H NMR, 13C NMR, elemental, and mass spectral analysis. All the compounds exhibited moderate

  一系列新颖的磺酰基衍生物3-（取代的苄基磺酰基）-5-（4-异丙基噻唑-2-基）-4-苯基-4H-1,2,4-三唑4a – 4e，异丙基噻唑衍生的席夫碱8a –合成了8l和2-（取代的苄基磺酰基）-5-（4-异丙基噻唑-2-基）-1,3,4-恶二唑11a - 11e并通过IR，1 H NMR，13 C NMR，元素和质谱分析。所有化合物均表现出中度至重要的抗菌和抗真菌活性。抗结核分枝杆菌H37Rv的抗结核筛选结果可确定化合物4e，8b，与一线药物异烟肼（0.25μg/ mL）相比，8f是出色的抗结核分子。
• Synthesis and pharmacological evaluation of novel 4-isopropylthiazole-4-phenyl-1,2,4-triazole derivatives as potential antimicrobial and antitubercular agents
  作者：G. V. Suresh Kumar、Y. Rajendra Prasad、S. M. Chandrashekar

  DOI：10.1007/s00044-012-0092-0

  日期：2013.2

  A series of novel 4-isopropylthiazol-4-phenyl-1,2,4-triazol derivatives, N'-(substituted benzylidene)-2-(5-(4-isopropylthiazol-2-yl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)acetohydrazides 4a-e, 4-isopropylthiazol-2-yl-4'-phenyl-4'H-1', 2',4'-triazol-3'-ylthio (substituted methyl benzylidene) acetohydrazides 5a-f, 3-(4-isopropylthiazol-2-yl)-4-phenyl-5-(5-substituted-1,3,4-oxadiazol-2-ylthio)-4H-1,2,4-triazole derivatives 6a-f and N-acetyl-5'-(4-isopropylthiazol-2-yl)-4'-phenyl-4'H-1,2,4-triazol-3'-ylthio) acetohydrazide 7 were synthesized and characterized by spectroscopy, elemental, and mass spectral analysis. These compounds were evaluated for their preliminary in vitro antibacterial, antifungal, and antitubercular activity against Mycobacterium tuberculosis (M. tuberculosis) H37Rv strain by broth dilution assay method. All the compounds exhibited moderate to significant antibacterial and antifungal activities. Results of the antitubercular screening against Mycobacterium tuberculosis H37Rv showed that compounds 4c and 6c exhibited good antitubercular activity when compared with first line drug isoniazid.