Methyl 2-(dimethylamino)benzo[d]oxazole-6-carboxylate | 1426528-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: Methyl 2-(dimethylamino)benzo[d]oxazole-6-carboxylate
• 英文别名: methyl 2-(dimethylamino)-1,3-benzoxazole-6-carboxylate
• CAS: 1426528-49-5
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: QYKREGWWUVWBLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-(dimethylamino)benzo[d]oxazole-6-carboxylate 在 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  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 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 Methyl 2-(dimethylamino)benzo[d]oxazole-6-carboxylate
  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

• [EN] ANTIBACTERIAL COMPOUNDS AND METHODS FOR USE<br/>[FR] COMPOSÉS ANTIBACTÉRIENS ET LEURS MÉTHODES D'UTILISATION
  申请人：PTC THERAPEUTICS INC

  公开号：WO2013033258A1

  公开（公告）日：2013-03-07

  The present description relates to compounds and forms and pharmaceutical compositions thereof and methods for use thereof to treat or ameliorate bacterial infections caused by wild-type and multi-drug resistant Gram-negative and Gram-positive pathogens.

  本文描述了化合物、形式及其制药组合物以及使用方法，用于治疗或缓解由野生型和多重耐药革兰氏阴性和革兰氏阳性病原体引起的细菌感染。
• ANTIBACTERIAL COMPOUNDS AND METHODS FOR USE
  申请人：PTC THERAPEUTICS, INC.

  公开号：US20150038437A1

  公开（公告）日：2015-02-05

  The present description relates to compounds and forms and pharmaceutical compositions thereof and methods for use thereof to treat or ameliorate bacterial infections caused by wild-type and multi-drug resistant Gram-negative and Gram-positive pathogens.

  本说明涉及化合物和形式以及其制药组合物，以及使用它们治疗或改善由野生型和多重耐药革兰氏阴性和革兰氏阳性病原体引起的细菌感染的方法。
• Antibacterial compounds and methods for use
  申请人：Branstrom Arthur

  公开号：US09409905B2

  公开（公告）日：2016-08-09

  The present description relates to compounds and forms and pharmaceutical compositions thereof and methods for use thereof to treat or ameliorate bacterial infections caused by wild-type and multi-drug resistant Gram-negative and Gram-positive pathogens.

  本说明涉及化合物及其形式和制药组合物，以及使用它们的方法，以治疗或改善由野生型和多重耐药革兰氏阴性和革兰氏阳性病原体引起的细菌感染。
• Cobalt-Catalyzed Hypervalent Iodine(III) Promoted Cascade Annulation Reaction of Anilines with Formamides for 2-Aminobenzoxazoles Synthesis
  作者：Lipeng Long、Xin Li、Yu Wang、Xing Su、Liang Qiao、Wenjun Luo、Zhengwang Chen

  DOI：10.1021/acs.joc.3c00547

  日期：2023.6.2

  were used as substrates. The C–H bond ortho to the amino group in the anilines was directly functionalized under cobalt-catalyzed conditions with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a Lewis acid for this reaction. The mechanism study showed that this transformation may involve a radical process.

  在此，我们公开了一种实用且简单的合成 2-氨基苯并恶唑的方法。简单的苯胺和甲酰胺用作底物。苯胺中氨基邻位的 C-H 键在钴催化条件下直接功能化，具有高水平的官能团耐受性。高价碘 (III) 既是氧化剂又是该反应的路易斯酸。机制研究表明，这种转变可能涉及一个激进的过程。
• US9409905B2
  申请人：——

  公开号：US9409905B2

  公开（公告）日：2016-08-09