5-(4-isothiocyanatophenyl)-1,3,4-oxadiazole-2-thiol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-isothiocyanatophenyl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-(4-isothiocyanatophenyl)-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₉H₅N₃OS₂
• 分子量: 235.29
• InChiKey: VBGZBLOXMSJIRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-isothiocyanatophenyl)-1,3,4-oxadiazole-2-thiol 在 三乙胺 作用下， 以 丙酮 、 苯 为溶剂， 反应 5.0h， 生成 2-hydroxyethylamino-4-(5-methylsulfanyl-1,3,4-oxadiazol-2-yl)anilinomethanethione
  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
• 作为产物：
  描述：

  4-氨基苯甲酰肼 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 28.0h， 生成 5-(4-isothiocyanatophenyl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  THE LITTLE MOLECULE COMPOUND WHICH USED FOR PROMOTING THE STEM CELLS HYPERPLASIA AND THE USE THEREOF

  摘要：

  该发明提供了能够加速干细胞增殖的小分子化合物及其用途。这些化合物在干细胞增殖机制研究中发挥着重要作用。该发明还涉及这些化合物及相关化合物在制备干细胞增殖加速剂和加速干细胞增殖的药物中的用途。该发明还涉及这些化合物在制备用于治疗由功能细胞丧失或损伤引起的各种疾病的药物中的用途。由干细胞创伤引起的疾病包括与神经系统细胞退化或损伤有关的疾病、血液系统疾病、与心血管细胞丧失或损伤有关的疾病、皮肤烧伤等。

  公开号：

  US20120053214A1

文献信息

• THE LITTLE MOLECULE COMPOUND WHICH USED FOR PROMOTING THE STEM CELLS HYPERPLASIA AND THE USE THEREOF
  申请人：Han Mei

  公开号：US20120053214A1

  公开（公告）日：2012-03-01

  The invention provides small molecule compounds capable of accelerating proliferation of stem cells and uses thereof. The compounds play an important role in the research of stem cell proliferation mechanism. The invention further relates to the uses of the compounds and relevant compounds thereof in the preparation of stem cell proliferation accelerators and the preparation of medicines accelerating stem cell proliferation. The invention also relates to the uses of the compounds in the preparation of medicines for the treatment of various diseases arising from functional cells loss or damage. The diseases arising from stem cell trauma comprise diseases related to the degeneration or damage of nervous system cells, blood system diseases, diseases related to the loss or damage of cardiovascular cells, skin burn and the like.

  该发明提供了能够加速干细胞增殖的小分子化合物及其用途。这些化合物在干细胞增殖机制研究中发挥着重要作用。该发明还涉及这些化合物及相关化合物在制备干细胞增殖加速剂和加速干细胞增殖的药物中的用途。该发明还涉及这些化合物在制备用于治疗由功能细胞丧失或损伤引起的各种疾病的药物中的用途。由干细胞创伤引起的疾病包括与神经系统细胞退化或损伤有关的疾病、血液系统疾病、与心血管细胞丧失或损伤有关的疾病、皮肤烧伤等。
• Rusu, G. G.; Gutsu, Ya. E.; Barba, N. A., Russian Journal of Organic Chemistry, 1995, vol. 31, # 11, p. 1547 - 1548
  作者：Rusu, G. G.、Gutsu, Ya. E.、Barba, N. A.

  DOI：——

  日期：——
• 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.
• Synthesis and biological evaluation of a novel human stem/progenitor cells proliferation activator: 4-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) thiosemicarbazide (Stemazole)
  作者：Ying Sun、Wei Wang、Yuanyuan Sun、Mei Han

  DOI：10.1016/j.ejmech.2011.04.017

  日期：2011.7

  Stem/progenitor cells are crucial for cell-based therapy and regenerative medicine, and their application in clinical and basic research requires a large supply of cells. To identify effective stem/progenitor cell proliferation activators, we synthesised a series of new 4-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl) thiosemicarbazide (named Stemazole) derivatives. Preliminary evaluation of the structure-activity relationship (SAR) and the biological activities of the compounds were determined with a luminescent cell viability assay. The identified leading compound, Stemazole, exhibited remarkable proliferation-promoting activity in human hippocampal stem/progenitor cells (HSCs) in a time-dependent and concentration-dependent manner. The proliferation-promoting activity of Stemazole was further confirmed against a panel of human stem/progenitor cells derived from each of the three blastoderm layers. In conclusion, Stemazole is a novel activator of stem cells proliferation. (C) 2011 Elsevier Masson SAS. All rights reserved.