3,3-dimethyl-5-oxo-5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-((3-(pyrrolidin-1-yl)propyl)amino)ethyl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)pentanoic acid | 1025069-83-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,3-dimethyl-5-oxo-5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-((3-(pyrrolidin-1-yl)propyl)amino)ethyl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)pentanoic acid
• 英文别名: (3β)-28-[[[3-(1-pyrrolidinyl)propyl]amino]methyl]lup-20(29)-en-3-ol; hydrogen 3,3-dimethylpetanedioate；5-[[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-3a-[2-(3-pyrrolidin-1-ylpropylamino)ethyl]-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-3,3-dimethyl-5-oxo-pentanoic acid；5-[[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-3a-[2-(3-pyrrolidin-1-ylpropylamino)ethyl]-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-3,3-dimethyl-5-oxopentanoic acid
• CAS: 1025069-83-3
• 化学式: C₄₅H₇₆N₂O₄
• 分子量: 709.109
• InChiKey: YZXLRUIHUNAQKZ-RAPNNLJQSA-N

物化性质

• 沸点：
  734.3±45.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1‐((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)‐3a‐(2‐methoxyvinyl)‐5a,5b,8,8,11a‐pentamethyl‐1‐(prop‐1‐en‐2‐yl)icosahydro‐1H‐cyclopenta[a]chrysen‐9‐yl)5‐methyl 3,3‐dimethylpentanedioate 在 氢氧化钾 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 96.16h， 生成 3,3-dimethyl-5-oxo-5-(((1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-3a-(2-((3-(pyrrolidin-1-yl)propyl)amino)ethyl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)pentanoic acid
  参考文献：
  名称：

  WO2008/57420

  摘要：

  公开号：

文献信息

• Alkyl Amine Bevirimat Derivatives Are Potent and Broadly Active HIV-1 Maturation Inhibitors
  作者：Emiko Urano、Sherimay D. Ablan、Rebecca Mandt、Gary T. Pauly、Dina M. Sigano、Joel P. Schneider、David E. Martin、Theodore J. Nitz、Carl T. Wild、Eric O. Freed

  DOI：10.1128/aac.02121-15

  日期：2016.1

  polymorphisms in SP1, we carried out an extensive medicinal chemistry campaign to develop novel maturation inhibitors. In this study, we focused on alkyl amine derivatives modified at the C-28 position of the BVM scaffold. We identified a set of derivatives that are markedly more potent than BVM against an HIV-1 clade B clone (NL4-3) and show robust antiviral activity against a variant of NL4-3 containing

  与从感染细胞中释放人类1型免疫缺陷病毒（HIV-1）颗粒相伴，病毒蛋白酶会在多个位点切割Gag多蛋白前体，从而触发病毒成熟。我们以前曾报道过，一种由桦木酸衍生的化合物bevirimat（BVM）通过破坏蛋白酶介导的Gag加工的后期步骤来阻止HIV-1成熟：衣壳-间隔物肽1（CA-SP1）中间至成熟的裂解CA。在多项临床试验中显示，BVM在减少HIV-1感染患者的病毒载量方面是安全有效的。但是，在Gag的SP1区域（例如SP1-V7A）中自然发生的多态性在某些接受BVM治疗的患者中导致可变的反应。SP1多态性HIV-1对BVM的敏感性降低导致其临床开发中断。为了克服SP1中由多态性引起的BVM活性的丧失，我们开展了广泛的药物化学研究，以开发新型的成熟抑制剂。在这项研究中，我们专注于在BVM支架的C-28位置修饰的烷基胺衍生物。我们确定了一组衍生物，对HIV-1进化枝B克隆（NL4-3）的效力
• Extended Triterpene Derivatives
  申请人：Myrexis, Inc.

  公开号：US20170096446A1

  公开（公告）日：2017-04-06

  The present invention concerns novel pharmaceutically active triterpene derivatives, pharmaceutical compositions containing the same, their use as medicaments, and the use of the compounds for the manufacture of specific medicaments. The present invention also concerns a method of treatment involving administration of the compounds. Specifically, the compounds are derivatives of betulinic acid having substitutions at one or more of the C-3, C2-8 and C-19 positions as further described herein. The novel compounds are useful as antiretroviral agents. In particular, the novel compounds are useful for the treatment of Human Immunodeficiency Virus (HIV).
• US9505800B2
  申请人：——

  公开号：US9505800B2

  公开（公告）日：2016-11-29