3(R)-tert-butyl-3-methyl-5(R)-phenyl-2-morpholinone | 185537-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 3(R)-tert-butyl-3-methyl-5(R)-phenyl-2-morpholinone
• 英文别名: (3R,5R)-3-(1,1-dimethylethyl)-3-methyl-5-phenylmorpholin-2-one；(3R,5R)-3-(tert-Butyl)-3-methyl-5-phenylmorpholin-2-one；(3R,5R)-3-tert-butyl-3-methyl-5-phenylmorpholin-2-one
• CAS: 185537-77-3
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: UHBUASKHQQJZGK-WFASDCNBSA-N

物化性质

• 沸点：
  382.1±42.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3(R)-tert-butyl-3-methyl-5(R)-phenyl-2-morpholinone 在 lithium aluminium tetrahydride 、 18-冠醚-6 、 氢气 、 palladium(II) hydroxide 、 potassium 2-methylbutan-2-olate 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 benzyl (1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-8-[(1R)-1,2-dimethylpropyl]-14-methoxy-15-[[(2R)-2,3,3-trimethyl-2-[[(4-methylphenyl)sulfonyl]amino]butyl]oxy]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylate
  参考文献：
  名称：

  Ibrexafungerp. 1,3-Beta-Glucan synthase inhibitor, Triterpenoid antifungal agent

  摘要：

  Fungal pathogens are responsible for a large number of mild to severe infections worldwide resulting in 1.6 million deaths. With the rapid emergence of drug resistance, the treatment of fungal infections is rapidly becoming unmanageable. Thus, the discovery and development of novel antifungal drugs is an unmet need of the hour. In this context, ibrexafungerp (SCY-078; SCYNEXIS) is the first orally bioavailable agent that has activity against beta-glucan synthase, an essential component of the cell wall. It has broad-spectrum activity against a wide range of Candida sp, including those that are resistant to echinocandins. In addition, ibrexafungerp exhibits broad-spectrum fungicidal activity including against multidrug-resistant strains, possesses high tissue penetration and exhibits flexible dosing options including via oral and intravenous routes. The U.S. Food and Drug Administration has granted both qualified infectious disease product and fast track designations for the oral formulation of ibrexafungerp for the treatment and prevention of recurrent vulvovaginal candidiasis.

  DOI：

  10.1358/dof.2019.44.4.2962844
• 作为产物：
  描述：

  D-苯甘氨醇 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 2,2,2-三氟乙醇 为溶剂， 生成 3(R)-tert-butyl-3-methyl-5(R)-phenyl-2-morpholinone
  参考文献：
  名称：

  Ibrexafungerp. 1,3-Beta-Glucan synthase inhibitor, Triterpenoid antifungal agent

  摘要：

  Fungal pathogens are responsible for a large number of mild to severe infections worldwide resulting in 1.6 million deaths. With the rapid emergence of drug resistance, the treatment of fungal infections is rapidly becoming unmanageable. Thus, the discovery and development of novel antifungal drugs is an unmet need of the hour. In this context, ibrexafungerp (SCY-078; SCYNEXIS) is the first orally bioavailable agent that has activity against beta-glucan synthase, an essential component of the cell wall. It has broad-spectrum activity against a wide range of Candida sp, including those that are resistant to echinocandins. In addition, ibrexafungerp exhibits broad-spectrum fungicidal activity including against multidrug-resistant strains, possesses high tissue penetration and exhibits flexible dosing options including via oral and intravenous routes. The U.S. Food and Drug Administration has granted both qualified infectious disease product and fast track designations for the oral formulation of ibrexafungerp for the treatment and prevention of recurrent vulvovaginal candidiasis.

  DOI：

  10.1358/dof.2019.44.4.2962844

文献信息

• Antifungal agents
  申请人：Greenlee Mark L.

  公开号：US20100113439A1

  公开（公告）日：2010-05-06

  Novel derivatives of enfumafungin are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antifungal agents and/or inhibitors of (1,3)-β-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and/or preventing fungal infections and associated diseases and conditions.

  本文披露了恩福马富金的新型衍生物，以及它们的药用盐、水合物和前药。还公开了包含这些化合物的组合物、制备这些化合物的方法以及将这些化合物用作抗真菌剂和/或(1,3)-β-D-葡聚糖合酶抑制剂的方法。这些公开的化合物、它们的药用盐、水合物和前药，以及包含这些化合物、盐、水合物和前药的组合物，可用于治疗和/或预防真菌感染及相关疾病和病况。
• ANTIFUNGAL AGENTS
  申请人：Greenlee Mark L

  公开号：US20110224228A1

  公开（公告）日：2011-09-15

  Novel derivatives of enfumafungin are disclosed herein, along with' their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and method of using such compounds as antifungal agents and/or inhibitors of (1,3)-β-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and/or preventing fungal infections and associated diseases and conditions.

  本文披露了恩福马富金的新衍生物，以及它们的药物可接受的盐、水合物和前药。还披露了包含这些化合物的组合物，制备这些化合物的方法以及将这些化合物用作抗真菌剂和/或(1,3)-β-D-葡聚糖合酶的抑制剂的方法。所披露的化合物、它们的药物可接受的盐、水合物和前药，以及包含这些化合物、盐、水合物和前药的组合物，对于治疗和/或预防真菌感染和相关疾病和病况是有用的。
• [EN] ANTIFUNGAL AGENTS<br/>[FR] AGENTS ANTIFONGIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2010019203A8

  公开（公告）日：2011-03-17
• US8188085B2
  申请人：——

  公开号：US8188085B2

  公开（公告）日：2012-05-29
• US8722727B2
  申请人：——

  公开号：US8722727B2

  公开（公告）日：2014-05-13