3-cyano-4-(3-hydroxyphenyl)-1,2,5-oxadiazole 2-oxide | 1147335-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-cyano-4-(3-hydroxyphenyl)-1,2,5-oxadiazole 2-oxide
• 英文别名: 4-(3-hydroxyphenyl)-2-oxido-1,2,5-oxadiazol-2-ium-3-carbonitrile
• CAS: 1147335-67-8
• 化学式: C₉H₅N₃O₃
• 分子量: 203.157
• InChiKey: HXBPIIAYBMAULA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-cyano-4-(3-methoxyphenyl)-1,2,5-oxadiazole 2-oxide 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 3-cyano-4-(3-hydroxyphenyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  [EN] OXADIAZOLE-2-OXIDES AS ANTISCHISTOSOMAL AGENTS
  [FR] OXADIAZOLE-2-OXYDES EN TANT QU'AGENTS ANTISCHISTOSOMIAUX

  摘要：

  公开号：

  WO2010019772A3

文献信息

• OXADIAZOLE-2-OXIDES AS ANTISCHISTOSOMAL AGENTS
  申请人：Thomas Craig J.

  公开号：US20110207784A1

  公开（公告）日：2011-08-25

  The invention provides 1,2,5-oxadiazole-containing compounds of Formula (I), wherein R 1 , A, and R 2 are as defined herein, that are useful in treating schistosomiasis. The invention also provides a composition comprising a pharmaceutically suitable carrier and at least one compound of the invention, and a method of treating schistosomiasis in a mammal.

  该发明提供了公式（I）中含有1,2,5-噁二唑基团的化合物，其中R1、A和R2如本文所定义，可用于治疗血吸虫病。该发明还提供了一种包含药学适用载体和至少一种该发明化合物的组合物，以及一种治疗哺乳动物血吸虫病的方法。
• Structure Mechanism Insights and the Role of Nitric Oxide Donation Guide the Development of Oxadiazole-2-Oxides as Therapeutic Agents against Schistosomiasis
  作者：Ganesha Rai、Ahmed A. Sayed、Wendy A. Lea、Hans F. Luecke、Harinath Chakrapani、Stefanie Prast-Nielsen、Ajit Jadhav、William Leister、Min Shen、James Inglese、Christopher P. Austin、Larry Keefer、Elias S. J. Arnér、Anton Simeonov、David J. Maloney、David L. Williams、Craig J. Thomas

  DOI：10.1021/jm901021k

  日期：2009.10.22

  Schistosomiasis is a chronic parasitic disease affecting hundreds of millions of individuals worldwide. Current treatment depends on a single agent, praziquantel, raising concerns of emergence of resistant parasites. Here, we continue our explorations of an oxadiazole-2-oxide class of compounds we recently identified as inhibitors of thioredoxin glutathione reductase (TGR), a selenocysteine-containing flavoenzyme required by the parasite to maintain proper cellular redox balance. Through systematic evaluation of the core molecular structure of this chemotype, we define the essential pharmacophore, establish a link between the nitric oxide donation and TGR inhibition, determine the selectivity for this chemotype versus related reductase enzymes, and present evidence that these agents can be modified to possess appropriate drug metabolism and pharmacokinetic properties. The mechanistic link between exogenous NO donation and parasite injury is expanded and better defined. The results of these studies verify the utility of oxadiazole-2-oxides as novel inhibitors of TGR and as efficacious antischistosomal agents.
• [EN] OXADIAZOLE-2-OXIDES AS ANTISCHISTOSOMAL AGENTS<br/>[FR] OXADIAZOLE-2-OXYDES EN TANT QU'AGENTS ANTISCHISTOSOMIAUX
  申请人：US HEALTH

  公开号：WO2010019772A3

  公开（公告）日：2010-08-26
• Synthesis of oxadiazole-2-oxide analogues as potential antischistosomal agents
  作者：Ganesha Rai、Craig J. Thomas、William Leister、David J. Maloney

  DOI：10.1016/j.tetlet.2009.01.120

  日期：2009.4

  The synthesis of several 1,2,5-oxadiazole-2-oxide (Furoxan) analogues is described herein. These compounds were prepared in an effort to probe the SAR around the phenyl substituent and oxadiazole core for our studies toward thioredoxin-glutathione reductase (TGR) inhibition and antischistosomal activity. Published by Elsevier Ltd.