(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(2-iodoacetyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid | 1071159-03-9

• 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: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(2-iodoacetyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 1071159-03-9
• 化学式: C₃₂H₄₉IO₄
• 分子量: 624.643
• InChiKey: FTNVUBURKHJRNN-ZZJQNEBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氯苯甲酰乙腈 、 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(2-iodoacetyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.0h， 以120 mg的产率得到(3S)-O-(N-methoxyglycyl)betulinic acid
  参考文献：
  名称：

  Enhancing the Divergent Activities of Betulinic Acid via Neoglycosylation

  摘要：

  Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, on the basis of the appended sugar, into two distinct compound subsets.

  DOI：

  10.1021/ol8025704
• 作为产物：
  描述：

  3-O-(chloroacetyl)betulinic acid 在 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 0.67h， 生成 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(2-iodoacetyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
  参考文献：
  名称：

  Enhancing the Divergent Activities of Betulinic Acid via Neoglycosylation

  摘要：

  Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, on the basis of the appended sugar, into two distinct compound subsets.

  DOI：

  10.1021/ol8025704

文献信息

• ANTIVIRAL PHOSPHONATE ANALOGS
  申请人：Boojamra Constantine G.

  公开号：US20090275535A1

  公开（公告）日：2009-11-05

  The invention is related to phosphorus substituted compounds with antiviral activity, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及具有抗病毒活性的磷取代化合物，包含这种化合物的组合物以及包括给予这种化合物的治疗方法，还包括用于制备这种化合物的过程和中间体。
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  公开（公告）日：2015-09-22