2-((4-bromobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole | 915889-32-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-((4-bromobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole
• 英文别名: 4-{5-[(4-Bromobenzyl)sulfanyl]-1,3,4-oxadiazol-2-yl}pyridine；2-[(4-bromophenyl)methylsulfanyl]-5-pyridin-4-yl-1,3,4-oxadiazole
• CAS: 915889-32-6
• 化学式: C₁₄H₁₀BrN₃OS
• 分子量: 348.223
• InChiKey: GYJQIJVEIAFBGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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：
  77.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异烟酸乙酯 在 一水合肼 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 生成 2-((4-bromobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Bioactivities of Novel 1,3,4-oxadiazole Derivatives Containing Pyridine Moiety

  摘要：

  本文通过多步反应在微波辅助条件下合成了一系列含有4-吡啶基的新型1,3,4-噁二唑衍生物，并利用1H NMR、MS和元素分析对其结构进行了表征。对目标化合物的杀菌活性进行了评估，结果表明，部分标题化合物展现出了良好的抗真菌活性。

  DOI：

  10.2174/1570180811666140522002929

文献信息

• SMALL MOLECULE INHIBITORS OF SUPEROXIDE DISMUTASE EXPRESSION
  申请人：Northwestern University

  公开号：US20160214969A1

  公开（公告）日：2016-07-28

  Disclosed are new small molecules and the uses thereof for inhibiting superoxide dismutase (SOD) expression. Also disclosed are pharmaceutical compositions comprising the small molecule inhibitors which may be administered in methods of treating diseases or disorders associated with elevated SOD expression or activity, including neurological diseases and disorders such as amyotrophic lateral sclerosis (ALS).

  公开了新的小分子及其用途，用于抑制超氧化物歧化酶（SOD）的表达。还公开了包含所述小分子抑制剂的药物组合物，该药物组合物可以通过用于治疗与SOD表达或活性升高相关的疾病或失调的方法来给药，包括神经疾病和失调，如肌萎缩侧索硬化症（ALS）。
• Synthesis and Bioactivities of Novel 1,3,4-oxadiazole Derivatives Containing Pyridine Moiety
  作者：Guo-Xiang Sun、Yan-Xia Shi、Zhao-Hui Sun、Ming-Yan Yang、Hong-Ke Wu、Jian-Quan Weng、Cheng-Xia Tan、Xing-Hai Liu、Bao-Ju Li、Yong-Gang Zhang

  DOI：10.2174/1570180811666140522002929

  日期：2014.8.31

  In this paper, some novel 1,3,4-oxadiazole derivatives containing 4-pyridyl group were synthesized under microwave assistant condition by multi-step reactions. The structures were characterized by 1H NMR, MS and elemental analyses. The target compounds were evaluated for their fungicidal activities, and the results indicated that some of the title compounds displayed good antifungal activities.

  本文通过多步反应在微波辅助条件下合成了一系列含有4-吡啶基的新型1,3,4-噁二唑衍生物，并利用1H NMR、MS和元素分析对其结构进行了表征。对目标化合物的杀菌活性进行了评估，结果表明，部分标题化合物展现出了良好的抗真菌活性。
• US9669014B2
  申请人：——

  公开号：US9669014B2

  公开（公告）日：2017-06-06
• [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).
• Discovery of 1,3,4-oxidiazole scaffold compounds as inhibitors of superoxide dismutase expression
  作者：Thomas J. Lukas、Gary E. Schiltz、Hasan Arrat、Karl Scheidt、Teepu Siddique

  DOI：10.1016/j.bmcl.2014.01.078

  日期：2014.3

  The treatment of neurodegenerative diseases is difficult because of multiple etiologies and the interplay of genetics and environment as precipitating factors. In the case of amyotrophic lateral sclerosis (ALS), we have knowledge of a handful of genes that cause disease when mutated. However, drugs to counteract the effect of genetic mutations have not yet been found. One of the causative genes, Cu, Zn-superoxide dismutase (SOD1) is responsible for about 10-15% of the genetically linked autosomal dominant disease. Our rationale was that compounds that reduce expression of the mutant protein would be beneficial to slow onset and/or disease progression. We screened candidate compounds using a cell-based in vitro assay for those that reduce mutant SOD1 (G93A) protein expression. This led to the discovery of 2-[3-iodophenyl) methylsulfanyl]-5pyridin-4-yl-1,3,4-oxadiazole, a known protein kinase inhibitor that decreases G93A-SOD1 expression in vitro and in the brain and spinal cord in vivo. However, this compound has a biphasic dose response curve and a likely toxophore which limit its therapeutic window for chronic disease such as ALS. Therefore, we designed and tested a focused library of analogs for their ability to decrease SOD1 expression in vitro. This exercise resulted in the identification of a lead compound with improved drug-like characteristics and activity. Development of small molecules that reduce the expression of etiologically relevant toxic proteins is a strategy that may also be extended to familial ALS linked to gain of function mutations in other genes. (C) 2014 The Authors. Published by Elsevier Ltd.