2-(benzylthio)-5-(4-nitrophenyl)-1,3,4-oxadiazole | 58695-72-0

• 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: 2-(benzylthio)-5-(4-nitrophenyl)-1,3,4-oxadiazole
• 英文别名: 2-benzylsulfanyl-5-(4-nitro-phenyl)-[1,3,4]oxadiazole；2-Benzylthio-5-p-nitrophenyl-1,3,4-oxadiazol；2-(Benzylsulfanyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole；2-benzylsulfanyl-5-(4-nitrophenyl)-1,3,4-oxadiazole
• CAS: 58695-72-0
• 化学式: C₁₅H₁₁N₃O₃S
• 分子量: 313.337
• InChiKey: GSTDADMQZFZMJY-UHFFFAOYSA-N

物化性质

• 熔点：
  201 °C
• 沸点：
  509.7±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(benzylthio)-5-(4-nitrophenyl)-1,3,4-oxadiazole 、 双氧水 以66%的产率得到
  参考文献：
  名称：

  GIRI S.; SINGH H.; YADAV L. D. S., AGR. AND BIOL. CHEM. , 1976, 40, NO 1, 17-21

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲酸甲酯 在 一水合肼 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 2-(benzylthio)-5-(4-nitrophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Structure-based optimization of oxadiazole-based GSK-3 inhibitors

  摘要：

  Inhibition of glycogen synthase kinase-3 (GSK-3) induces neuroprotective effects, e.g. decreases beta-amyloid production and reduces tau hyperphosphorylation, which are both associated with Alzheimer's disease (AD). The two isoforms of GSK-3 in mammalians are GSK-3 alpha and beta, which share 98% homology in their catalytic domains. We investigated GSK-3 inhibitors based on 2 different scaffolds in order to elucidate the demands of the ATP-binding pocket [1]. Particularly, the oxadiazole scaffold provided potent and selective GSK-3 inhibitors. For example, the most potent inhibitor of the present series, the acetamide 26d, is characterized by an IC50 of 2 nM for GSK-3 alpha and 17 nM for GSK-3 beta. In addition, the benzodioxane 8g showed up to 27-fold selectivity for GSK-3 alpha over GSK-3 beta, with an IC50 of 35 nM for GSK-3 alpha. Two GSK-3 inhibitors were further profiled for efficacy and toxicity in the wild-type (wt) zebrafish embryo assay to evaluate simultaneously permeability and safety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.006

文献信息

• Exploring 2-(benzylthio)-5-(4-nitrophenyl)-1,3,4-oxadiazole as antiproliferative agent: Synthesis, single crystal XRD, DFT, Hirshfeld surface analysis, in vitro antiproliferative activity and molecular docking analysis
  作者：Riya Kumari、Shivendra K. Pandey、A.K. Patel、D. Kushwaha、A. Acharya、M.K. Bharty

  DOI：10.1016/j.molstruc.2024.138422

  日期：2024.9

  and NH···N hydrogen bonding weak interactions, which are quantitively examined through Hirshfeld surface analysis. The DFT calculations are also performed to verify physiochemical properties of and the results obtained are in good agreement with the experimental results. The HOMO and LUMO energy gap of 3.402 eV for indicates good NLO properties. The cytotoxic activity of against Dalton's lymphoma cells

  在本研究中，合成了恶二唑衍生物，即2-(苄硫基)-5-(4-硝基苯基)-1,3,4-恶二唑()。该研究深入探讨了其对从小鼠 T 细胞淋巴瘤中获得的道尔顿淋巴瘤 (DL) 肿瘤细胞的抗癌功效。该化合物已通过元素分析、红外、紫外-可见、核磁共振和单晶 X 射线衍射数据进行了表征。该化合物在空间群 P 21/n 的单斜晶系中结晶。晶体结构通过弱CH·O和NH·N氢键弱相互作用而稳定，通过赫什菲尔德表面分析定量检测。还进行了DFT计算来验证其理化性质，所得结果与实验结果吻合良好。 3.402 eV 的 HOMO 和 LUMO 能隙表明良好的 NLO 性能。通过MTT测定评估针对道尔顿淋巴瘤细胞的细胞毒活性。结果显示显着的抗癌功效，IC值为80 μg/mL。通过各种测定检查了化合物的作用模式，结果表明化合物通过下调线粒体膜电位和上调活性氧（ROS）产生来发挥作用。进行分子对接研究，以确定该化合物的细胞毒性与其在重要抗癌和抗凋亡靶蛋白
• ANWAR, M.;ABDEL-MEGEED, M. F.;ISLAM, I.;SOROUR, N., EGYPT. J. CHEM., 1981, 24, N 1-3, 117-126
  作者：ANWAR, M.、ABDEL-MEGEED, M. F.、ISLAM, I.、SOROUR, N.

  DOI：——

  日期：——
• [DE] DERIVATE VON 2-BENZYLSULFANYL[1,3,4]-OXADIAZOL UND DEREN MEDIZINISCHE VERWENDUNG<br/>[EN] 2-BENZYLSULFANYL[1,3,4]-OXADIAZOLE DERIVATIVES, AND MEDICAL USE THEREOF<br/>[FR] DÉRIVÉS DE 2-BENZYLSULFANYL[1,3,4]OXADIAZOLE ET UTILISATION DESDITS DÉRIVÉS EN MÉDECINE
  申请人：UNIV DARMSTADT TECH

  公开号：WO2013007663A1

  公开（公告）日：2013-01-17

  Die vorliegende Erfindung betrifft Verbindungen, die als selektive Liganden der Glykogen Synthase Kinase 3 (GSK-3) wirken und für die Behandlung von GSK-3-vermittelten Erkrankungen verwendet werden können. Die erfindungsgemäßen Verbindungen wirken als Inhibitoren der Glykogen Synthase Kinase 3 (GSK-3).
• Structure-based optimization of oxadiazole-based GSK-3 inhibitors
  作者：Fabio Lo Monte、Thomas Kramer、Jiamin Gu、Martin Brodrecht、Johannes Pilakowski、Ana Fuertes、Juan Manuel Dominguez、Batya Plotkin、Hagit Eldar-Finkelman、Boris Schmidt

  DOI：10.1016/j.ejmech.2012.06.006

  日期：2013.3

  Inhibition of glycogen synthase kinase-3 (GSK-3) induces neuroprotective effects, e.g. decreases beta-amyloid production and reduces tau hyperphosphorylation, which are both associated with Alzheimer's disease (AD). The two isoforms of GSK-3 in mammalians are GSK-3 alpha and beta, which share 98% homology in their catalytic domains. We investigated GSK-3 inhibitors based on 2 different scaffolds in order to elucidate the demands of the ATP-binding pocket [1]. Particularly, the oxadiazole scaffold provided potent and selective GSK-3 inhibitors. For example, the most potent inhibitor of the present series, the acetamide 26d, is characterized by an IC50 of 2 nM for GSK-3 alpha and 17 nM for GSK-3 beta. In addition, the benzodioxane 8g showed up to 27-fold selectivity for GSK-3 alpha over GSK-3 beta, with an IC50 of 35 nM for GSK-3 alpha. Two GSK-3 inhibitors were further profiled for efficacy and toxicity in the wild-type (wt) zebrafish embryo assay to evaluate simultaneously permeability and safety. (C) 2012 Elsevier Masson SAS. All rights reserved.
• GIRI S.; SINGH H.; YADAV L. D. S., AGR. AND BIOL. CHEM. <ABCH-A6>, 1976, 40, NO 1, 17-21
  作者：GIRI S.、 SINGH H.、 YADAV L. D. S.

  DOI：——

  日期：——