N'-[N-[3β-hydroxylup-20(29)-en-28-oyl]-6-aminohexanoyl]-L-proline | 1169880-08-3

• 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: N'-[N-[3β-hydroxylup-20(29)-en-28-oyl]-6-aminohexanoyl]-L-proline
• 英文别名: (2S)-1-[6-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-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-carbonyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
• CAS: 1169880-08-3
• 化学式: C₄₁H₆₆N₂O₅
• 分子量: 666.985
• InChiKey: KUEXKNFMYJLYLO-VZVRPCTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以38 mg的产率得到N'-[N-[3β-hydroxylup-20(29)-en-28-oyl]-6-aminohexanoyl]-L-proline
  参考文献：
  名称：

  Betulinic Acid Derivatives as Human Immunodeficiency Virus Type 2 (HIV-2) Inhibitors

  摘要：

  We previously reported that [[N-[3 beta-hydroxyllup-20(29)-en-28-oyl]-7-aminoheptyl]carbamoyl]methane (A43D, 4) was a potent HIV-1 entry inhibitor. However, 4 was inactive against HIV-2 virus, suggesting the structural requirements for targeting these two retroviruses are different. In this study, a series of new betulinic acid derivatives were synthesized, and some of them displayed selective anti-HIV-2 activity at nanomolar concentrations. In comparison to compounds with anti-HIV-1 activity, a shorter C-28 side chain is required for optimal anti-HIV-2 activity.

  DOI：

  10.1021/jm9004253