1-(thiophen-2-yl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one | 81234-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(thiophen-2-yl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one
• 英文别名: 1-(thiophen-2-yl)-3-(1H-1,2,4-triazol-1-yl)-1-propanone；1-Thiophen-2-yl-3-(1,2,4-triazol-1-yl)propan-1-one
• CAS: 81234-93-7
• 化学式: C₉H₉N₃OS
• 分子量: 207.256
• InChiKey: HCUHKYCMVBJATK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(thiophen-2-yl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one 在 sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 1-(3-(2,5-dichlorobenzyloxy)-3-(thiophen-2-yl)propyl)-1H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and evaluation of new furanyl and thiophenyl azoles as antileishmanial agents

  摘要：

  A series of benzyloxy furanyl and benzyloxy thiophenyl azoles were synthesized and screened for their in vitro antileishmanial activity against Leishmania donovani. Among all, 16 compounds have shown more than 90% inhibition against promastigotes at 20 mu M while 11 compounds exhibited IC50 in the range of 3.04-9.39 mu M against amastigotes. Compound 4, a 3-chlorobenzyloxy furanyl imidazole emerged as the most active compound in the series with IC50 value of 3.04 mu M and SI value of 19.80, and was several folds more potent than the reference drugs miltefosine and miconazole. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.021
• 作为产物：
  描述：

  2-乙酰基噻吩 在 盐酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 15.0h， 生成 1-(thiophen-2-yl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one
  参考文献：
  名称：

  Roman, Gheorghe, Acta Chimica Slovenica, 2013, vol. 60, # 1, p. 70 - 80

  摘要：

  DOI：

文献信息

• Copper-Catalyzed <i>N</i>-Arylation of Azoles and Mannich-Type Coupling of Ketones and Azoles under Metal-Free Conditions
  作者：Kai Sun、Zhonghong Zhu、Jingjing Sun、Lulu Liu、Xin Wang

  DOI：10.1021/acs.joc.5b02593

  日期：2016.2.19

  five-membered heterocycles with azoles. Five-membered heterocycles bearing an acetyl group also underwent a Mannich-type reaction with activated azoles to give the corresponding β-amino ketones under metal-free conditions. These reactions exhibited wide substrate scope, high functional group tolerance, and ease of operation, making them useful tools with numerous potential applications in synthetic chemistry

  已经开发出一种新的方法，用于五元杂环与唑的铜催化直接N-芳基化。在无金属条件下，带有乙酰基的五元杂环也与活化的唑类发生曼尼希型反应，得到相应的β-氨基酮。这些反应具有广泛的底物范围，较高的官能团耐受性和易于操作的特性，使其成为有用的工具，在合成化学中具有众多潜在应用。
• Synthesis and evaluation of new furanyl and thiophenyl azoles as antileishmanial agents
  作者：Vijay K. Marrapu、Monika Mittal、Rahul Shivahare、Suman Gupta、Kalpana Bhandari

  DOI：10.1016/j.ejmech.2011.02.021

  日期：2011.5

  A series of benzyloxy furanyl and benzyloxy thiophenyl azoles were synthesized and screened for their in vitro antileishmanial activity against Leishmania donovani. Among all, 16 compounds have shown more than 90% inhibition against promastigotes at 20 mu M while 11 compounds exhibited IC50 in the range of 3.04-9.39 mu M against amastigotes. Compound 4, a 3-chlorobenzyloxy furanyl imidazole emerged as the most active compound in the series with IC50 value of 3.04 mu M and SI value of 19.80, and was several folds more potent than the reference drugs miltefosine and miconazole. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Roman, Gheorghe, Acta Chimica Slovenica, 2013, vol. 60, # 1, p. 70 - 80
  作者：Roman, Gheorghe

  DOI：——

  日期：——