3-acetyl-5-phenyl-2-(5-nitrothiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole | 757217-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-acetyl-5-phenyl-2-(5-nitrothiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole
• 英文别名: 1-[2-(5-nitrothiophen-2-yl)-5-phenyl-1,3,4-oxadiazol-3(2H)-yl]ethanone；1-[2-(5-nitrothiophen-2-yl)-5-phenyl-2H-1,3,4-oxadiazol-3-yl]ethanone
• CAS: 757217-39-3
• 化学式: C₁₄H₁₁N₃O₄S
• 分子量: 317.325
• InChiKey: UUSQVTZBPLYRHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酸 在 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 13.17h， 生成 3-acetyl-5-phenyl-2-(5-nitrothiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and antifungal agents

  摘要：

  A series of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives was synthesized and their activity screened in vitro against Staphylococcus aureus, Trypanosoma cruzi, and Candida albicans. The bioactivity was expressed as minimum inhibitory concentration (MIC) for S. aureus strains, and as fifty-percent inhibitory concentration (IC50) of parasite population growth for T. cruzi. A molecular modeling approach was performed to establish qualitative relationships regarding the biological data and the compounds' physicochemical properties. The 5-(4-OC4H9Ph, 5l), and 5-(4-CO2CH3Ph, 5o) derivatives were the most active compounds for S. aureus ATCC 25923 (MIC = 1.95 - 1.25 mu g/mL) and T. cruzi (IC50 = 7.91 mu M), respectively. Also, a preliminary evaluation against C. albicans involving some compounds was performed and the 5-(4-CH3Ph, 5e) derivative was the most active compound (MIC = 3.28-2.95 mu g/mL). In this preliminary study, all synthesized 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives were active against all microorganisms tested. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.009

文献信息

• Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and antifungal agents
  作者：Marina Ishii、Salomão Dória Jorge、Alex Alfredo de Oliveira、Fanny Palace-Berl、Ieda Yuriko Sonehara、Kerly Fernanda Mesquita Pasqualoto、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2011.09.009

  日期：2011.11

  A series of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives was synthesized and their activity screened in vitro against Staphylococcus aureus, Trypanosoma cruzi, and Candida albicans. The bioactivity was expressed as minimum inhibitory concentration (MIC) for S. aureus strains, and as fifty-percent inhibitory concentration (IC50) of parasite population growth for T. cruzi. A molecular modeling approach was performed to establish qualitative relationships regarding the biological data and the compounds' physicochemical properties. The 5-(4-OC4H9Ph, 5l), and 5-(4-CO2CH3Ph, 5o) derivatives were the most active compounds for S. aureus ATCC 25923 (MIC = 1.95 - 1.25 mu g/mL) and T. cruzi (IC50 = 7.91 mu M), respectively. Also, a preliminary evaluation against C. albicans involving some compounds was performed and the 5-(4-CH3Ph, 5e) derivative was the most active compound (MIC = 3.28-2.95 mu g/mL). In this preliminary study, all synthesized 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives were active against all microorganisms tested. (C) 2011 Elsevier Ltd. All rights reserved.