2-(4-Methylpiperazin-1-yl)-1,3-benzoxazole-6-carboxylic acid | 1393746-55-8

• 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: 2-(4-Methylpiperazin-1-yl)-1,3-benzoxazole-6-carboxylic acid
• 英文别名: 2-(4-methylpiperazin-1-yl)-1,3-benzoxazole-6-carboxylic acid
• CAS: 1393746-55-8
• 化学式: C₁₃H₁₅N₃O₃
• mdl: MFCD27420483
• 分子量: 261.28
• InChiKey: ZTVWLCIORVDYIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-Methylpiperazin-1-yl)-1,3-benzoxazole-6-carboxylic acid 在 三甲基氯硅烷 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-2-(4-methylpiperazin-1-yl)benzo[d]oxazole-6-carboxamide
  参考文献：
  名称：

  Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors

  摘要：

  A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl) amino)-N-isobutylbenzo[d]oxazole-6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent 'boosting' properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.022
• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸甲酯 在 吡啶 、 水 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 2-(4-Methylpiperazin-1-yl)-1,3-benzoxazole-6-carboxylic acid
  参考文献：
  名称：

  Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors

  摘要：

  A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl) amino)-N-isobutylbenzo[d]oxazole-6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent 'boosting' properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.022

文献信息

• Benzoxazole and benzothiazole amides as novel pharmacokinetic enhancers of HIV protease inhibitors
  作者：Tim H.M. Jonckers、Marie-Claude Rouan、Geerwin Haché、Wim Schepens、Sabine Hallenberger、Judith Baumeister、Jennifer C. Sasaki

  DOI：10.1016/j.bmcl.2012.06.022

  日期：2012.8

  A new class of benzoxazole and benzothiazole amide derivatives exhibiting potent CYP3A4 inhibiting properties was identified. Extensive lead optimization was aimed at improving the CYP3A4 inhibitory properties as well as overall ADME profile of these amide derivatives. This led to the identification of thiazol-5-ylmethyl (2S,3R)-4-(2-(ethyl(methyl) amino)-N-isobutylbenzo[d]oxazole-6-carboxamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate (C1) as a lead candidate for this class. This compound together with structurally similar analogues demonstrated excellent 'boosting' properties when tested in dogs. These findings warrant further evaluation of their properties in an effort to identify valuable alternatives to Ritonavir as pharmacokinetic enhancers. (c) 2012 Elsevier Ltd. All rights reserved.