5-(4-(4-benzylpiperazin-1-yl)phenyl)-3-(5-nitrofuran-2-yl)-4,5-dihydroisooxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-(4-(4-benzylpiperazin-1-yl)phenyl)-3-(5-nitrofuran-2-yl)-4,5-dihydroisooxazole
• 英文别名: 5-(4-(4-benzylpiperazin-1-yl)phenyl)-3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol；5-[4-(4-Benzylpiperazin-1-yl)phenyl]-3-(5-nitro-2-furyl)-4,5-dihydroisoxazole；5-[4-(4-benzylpiperazin-1-yl)phenyl]-3-(5-nitrofuran-2-yl)-4,5-dihydro-1,2-oxazole
• 化学式: C₂₄H₂₄N₄O₄
• 分子量: 432.479
• InChiKey: AYYDKEZKHJTZMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(4-(3-(5-nitrofuran-2-yl)-4,5-dihydroisoxazol-5-yl)phenyl)piperazine-1-carboxylate 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-(4-(4-benzylpiperazin-1-yl)phenyl)-3-(5-nitrofuran-2-yl)-4,5-dihydroisooxazole
  参考文献：
  名称：

  Discovery of novel isoxazolines as anti-tuberculosis agents

  摘要：

  Nitrofuranyl isoxazolines with increased proteolytic stability over nitrofuranyl amides were designed and synthesized leading to discovery of several compounds with potent in vitro anti-tuberculosis activity. However, their in vivo activity was limited by high protein binding and poor distribution. Consequently, a series of non-nitrofuran containing isoxazolines were prepared to determine if the core had residual anti-tuberculosis activity. This led to the discovery of novel isoxazoline 12 as anti-tuberculosis agent with a MIC90 value of 1.56 mu g/mL. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.048

文献信息

• [EN] SUBSTITUTED 1,2,4-OXADIAZOLE, ITS APPLICATION AND A PHARMACEUTICAL PREPARATION COMPRISING IT<br/>[FR] 1,2,4-OXADIAZOLE SUBSTITUÉ, SON APPLICATION ET PRÉPARATION PHARMACEUTIQUE LE COMPRENANT
  申请人：SVENOX PHARMACEUTICALS LLC

  公开号：WO2020128675A1

  公开（公告）日：2020-06-25

  Substances effective against tuberculosis based on substituted 1,2,4-oxadiazoles of general formula I, where Y = S or CH2 and R = phenyl- or phenyl- substituted in positions 2, 3, 4, and 5 by one or several electron-acceptor groups or electron-donor groups. These compounds can be produced by easy syntheses and are characterized by low toxicity and high efficacy against mycobacteria, including multiresistant strains thereof. The invention also discloses a pharmaceutical preparation containing substituted 1,2,4-oxadiazole of formula I as active substance as well as the use of this substituted 1,2,4-oxadiazole as an antituberculosis drug.

  基于通式I的取代1,2,4-噁二唑，其中Y = S或CH2，R = 苯基或在2,3,4和5位上被一个或多个电子受体基团或电子给体基团取代的苯基。这些化合物可以通过简单的合成方法制备，并具有低毒性和高效抗结核分枝杆菌的特性，包括多重耐药菌株。本发明还揭示了一种含有通式I的取代1,2,4-噁二唑作为活性物质的药物制剂，以及将这种取代1,2,4-噁二唑用作抗结核药物的用途。
• SUBSTITUTED 1,2,4-OXADIAZOLE, ITS APPLICATION AND A PHARMACEUTICAL PREPARATION COMPRISING IT
  申请人：SVENOX PHARMACEUTICALS LLC

  公开号：US20210403443A1

  公开（公告）日：2021-12-30

  Disclosed are compounds effective against tuberculosis based on substituted 1,2,4-oxadiazoles of general formula I, where Y═S or CH 2 and R=phenyl- or phenyl-substituted in positions 2, 3, 4, and 5 by one or several electron-acceptor groups or electron-donor groups. These compounds can be produced by easy syntheses and are characterized by low toxicity and high efficacy against mycobacteria, including multiresistant strains thereof. Also disclosed are a pharmaceutical preparation containing substituted 1,2,4-oxadiazole of formula I as an active substance as well as the use of this substituted 1,2,4-oxadiazole as an antituberculosis drug.
• Discovery of novel isoxazolines as anti-tuberculosis agents
  作者：Rajendra P. Tangallapally、Dianqing Sun、Rakesh、Nageshwar Budha、Robin E.B. Lee、Anne J.M. Lenaerts、Bernd Meibohm、Richard E. Lee

  DOI：10.1016/j.bmcl.2007.09.048

  日期：2007.12

  Nitrofuranyl isoxazolines with increased proteolytic stability over nitrofuranyl amides were designed and synthesized leading to discovery of several compounds with potent in vitro anti-tuberculosis activity. However, their in vivo activity was limited by high protein binding and poor distribution. Consequently, a series of non-nitrofuran containing isoxazolines were prepared to determine if the core had residual anti-tuberculosis activity. This led to the discovery of novel isoxazoline 12 as anti-tuberculosis agent with a MIC90 value of 1.56 mu g/mL. (c) 2007 Elsevier Ltd. All rights reserved.