1-(4-fluorophenyl)-2-(4-[2-(hydroxyethylamino(thioxo)methyl)amino]phenyl-1,3,4-oxadiazol-2-ylsulfanyl)-1-ethanone | 1350301-84-6

• 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-(4-[2-(hydroxyethylamino(thioxo)methyl)amino]phenyl-1,3,4-oxadiazol-2-ylsulfanyl)-1-ethanone
• 英文别名: 1-[4-[5-[2-(4-Fluorophenyl)-2-oxo-ethyl]sulfanyl-1,3,4-oxadiazol-2-yl]phenyl]-3-(2-hydroxyethyl)thiourea；1-[4-[5-[2-(4-fluorophenyl)-2-oxoethyl]sulfanyl-1,3,4-oxadiazol-2-yl]phenyl]-3-(2-hydroxyethyl)thiourea
• CAS: 1350301-84-6
• 化学式: C₁₉H₁₇FN₄O₃S₂
• 分子量: 432.499
• InChiKey: HWTBJNCWIZJNMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(4-fluorophenyl)-2-[5-(4-isothiocyanatophenyl)-1,3,4-oxadiazol-2-ylsulfanyl]-1-ethanone 、 C.I.酸性橙108 以 苯 为溶剂， 反应 3.0h， 以85%的产率得到1-(4-fluorophenyl)-2-(4-[2-(hydroxyethylamino(thioxo)methyl)amino]phenyl-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.