1-(4-fluorophenyl)-2-[5-(3-isothiocyanatophenyl)-1,3,4-oxadiazol-2-ylsulfanyl]-1-ethanone | 1350302-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-fluorophenyl)-2-[5-(3-isothiocyanatophenyl)-1,3,4-oxadiazol-2-ylsulfanyl]-1-ethanone
• 英文别名: 1-(4-Fluorophenyl)-2-[[5-(3-isothiocyanatophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]ethanone
• CAS: 1350302-03-2
• 化学式: C₁₇H₁₀FN₃O₂S₂
• 分子量: 371.416
• InChiKey: VTQRCKMBKLAANR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-溴-4'-氟苯乙酮 、 5-(3-isothiocyanatophenyl)-1,3,4-oxadiazole-2-thiol 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以79%的产率得到1-(4-fluorophenyl)-2-[5-(3-isothiocyanatophenyl)-1,3,4-oxadiazol-2-ylsulfanyl]-1-ethanone
  参考文献：
  名称：

  The structure–antituberculosis activity relationships study in a series of 5-aryl-2-thio-1,3,4-oxadiazole derivatives

  摘要：

  A series of 82 5-aryl-2-thio-1,3,4-oxadiazole derivatives were screened for their anti-mycobacterial activities against Mycobacterium tuberculosis H37Rv. The synthesized compounds 30-37 appeared to be the most active derivatives exhibiting more than 90% inhibition of mycobacterial growth at 12.5 mu g/mL. Structure-activity relationships study was performed for the given series by using the electronic-topological method combined with neural networks (ETM-NN). A system for the anti-mycobacterial activity prediction was developed as the result of training associative neural network (ASNN) with weights calculated from projections of a compound and each pharmacophoric fragment found on the elements of the Kohonen's self-organizing maps (SOMs). From the detailed analysis of all compounds under study, the necessary requirements for a compound to possess antituberculosis activity have been formulated. The analysis has shown that any requirement's violation for a molecule implies a considerable decrease or even complete loss of its activity. Molecular docking studies of the compounds allowed shedding light on the binding mode of these novel anti-mycobacterial inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.038

文献信息

• The structure–antituberculosis activity relationships study in a series of 5-aryl-2-thio-1,3,4-oxadiazole derivatives
  作者：Fliur Macaev、Zinaida Ribkovskaia、Serghei Pogrebnoi、Veaceslav Boldescu、Ghenadie Rusu、Nathaly Shvets、Anatholy Dimoglo、Athina Geronikaki、Robert Reynolds

  DOI：10.1016/j.bmc.2011.09.038

  日期：2011.11

  A series of 82 5-aryl-2-thio-1,3,4-oxadiazole derivatives were screened for their anti-mycobacterial activities against Mycobacterium tuberculosis H37Rv. The synthesized compounds 30-37 appeared to be the most active derivatives exhibiting more than 90% inhibition of mycobacterial growth at 12.5 mu g/mL. Structure-activity relationships study was performed for the given series by using the electronic-topological method combined with neural networks (ETM-NN). A system for the anti-mycobacterial activity prediction was developed as the result of training associative neural network (ASNN) with weights calculated from projections of a compound and each pharmacophoric fragment found on the elements of the Kohonen's self-organizing maps (SOMs). From the detailed analysis of all compounds under study, the necessary requirements for a compound to possess antituberculosis activity have been formulated. The analysis has shown that any requirement's violation for a molecule implies a considerable decrease or even complete loss of its activity. Molecular docking studies of the compounds allowed shedding light on the binding mode of these novel anti-mycobacterial inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.