propyl (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-carboxylate | 1400262-26-1

• 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: propyl (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-carboxylate
• CAS: 1400262-26-1
• 化学式: C₃₃H₅₄O₃
• 分子量: 498.79
• InChiKey: HXSOBSAJOZEHED-ODLWIBRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-二甲基琥珀酸酐 、 propyl (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-carboxylate 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以46%的产率得到4-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-3a-propoxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid
  参考文献：
  名称：

  Anti-AIDS Agents 90. Novel C-28 Modified Bevirimat Analogues as Potent HIV Maturation Inhibitors

  摘要：

  In a continuing study of bevirimat (2), the anti-HIV-maturation clinical trials agent, 28 new betulinic acid (BA, 1) derivatives were designed and synthesized. Among these compounds, 17, with a C-28 MEM ester moiety, and 22, with a C-28 ethyl hexanoate, increased the anti-HIV replication activity compared with 2 by 2-fold while compounds 40, 41, 48, and 49, with C-28 piperazine or piperidine amide substitutions, increased the activity by 3- to 15-fold. The best new compound, 41, exhibited an anti-HIV IC50 of 0.0059 mu M compared with 0.087 mu M antimaturation effects, as confirmed by TZM-bl assay, in blocking the HIV replication. The results suggest that proper C-28 substitutions can further enhance the antimaturation activity of 2 without any antientry effects. Thus, 41 may serve as a promising new lead for development of anti-AIDS clinical trial candidates.

  DOI：

  10.1021/jm301040s
• 作为产物：
  描述：

  白桦脂酸 、 溴丙烷 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以86%的产率得到propyl (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-carboxylate
  参考文献：
  名称：

  Anti-AIDS Agents 90. Novel C-28 Modified Bevirimat Analogues as Potent HIV Maturation Inhibitors

  摘要：

  In a continuing study of bevirimat (2), the anti-HIV-maturation clinical trials agent, 28 new betulinic acid (BA, 1) derivatives were designed and synthesized. Among these compounds, 17, with a C-28 MEM ester moiety, and 22, with a C-28 ethyl hexanoate, increased the anti-HIV replication activity compared with 2 by 2-fold while compounds 40, 41, 48, and 49, with C-28 piperazine or piperidine amide substitutions, increased the activity by 3- to 15-fold. The best new compound, 41, exhibited an anti-HIV IC50 of 0.0059 mu M compared with 0.087 mu M antimaturation effects, as confirmed by TZM-bl assay, in blocking the HIV replication. The results suggest that proper C-28 substitutions can further enhance the antimaturation activity of 2 without any antientry effects. Thus, 41 may serve as a promising new lead for development of anti-AIDS clinical trial candidates.

  DOI：

  10.1021/jm301040s

文献信息

• Antitumor agent
  申请人：The Nisshin OilliO, Ltd.

  公开号：US20030153538A1

  公开（公告）日：2003-08-14

  The present invention relates to an antitumor agent, which comprises, as an effective component, a compound selected from the group consisting of maslinic acid, erythrodiol, uvaol, betulinic acid, betulin and physiologically acceptable salts thereof or derivatives thereof.

  本发明涉及一种抗肿瘤剂，其包括作为有效成分的化合物，所述化合物选自橄榄酸、赤藓醇、尤瓦醇、白桦酸、白桦醇及其生理接受的盐或衍生物的组。
• Feeds and fertilizers containing pentacyclic triterpenes
  申请人：The Nisshin OilliO, Ltd.

  公开号：US20040175447A1

  公开（公告）日：2004-09-09

  The present invention relates to a feed, a fertilizer, a melanogenesis-inhibitory agent for animals and plants and a blackening/browning-inhibitory composition for animals and plants, each comprising, as an effective component, at least one member selected from the group consisting of pentacyclic triterpenes, physiologically acceptable salts thereof and derivatives thereof, which have an excellent melanogenesis-inhibitory effect.

  本发明涉及一种饲料、一种肥料、一种动植物黑色素生成抑制剂和一种动植物黑化/褐化抑制组合物，每种均包括至少一种选自五环三萜、其生理上可接受的盐和衍生物组成的群体中的有效成分，具有出色的黑色素生成抑制效果。
• ANTITUMOR AGENTS
  申请人：The Nisshin Oillio, Ltd.

  公开号：EP1321145A1

  公开（公告）日：2003-06-25

  The present invention relates to an antitumor agent, which comprises, as an effective component, a compound selected from the group consisting of maslinic acid, erythrodiol, uvaol, betulinic acid, betulin and physiologically acceptable salts thereof or derivatives thereof.

  本发明涉及一种抗肿瘤剂，其有效成分包括选自马斯林酸、红景天二醇、莼菜醇、白桦脂酸、白桦脂素及其生理上可接受的盐或其衍生物的化合物。
• BEAUTIFYING FOODS AND DRINKS AND PERORAL BEAUTIFYING PREPARATIONS
  申请人：The Nisshin Oillio, Ltd.

  公开号：EP1340501A1

  公开（公告）日：2003-09-03

  The present invention relates to a food or beverage comprising at least one member selected from the group consisting of 5-membered ring-containing triterpenes and physiologically acceptable salts or derivatives thereof. The present invention also relates to an orally administered whitening agent comprising, as an effective component, at least one member selected from the group consisting of 5-membered ring-containing triterpenes and physiologically acceptable salts or derivatives thereof.

  本发明涉及一种食品或饮料，其中含有至少一种选自含五元环的三萜类化合物及其生理上可接受的盐或衍生物组成的组的成员。本发明还涉及一种口服美白剂，其有效成分包括至少一种选自含五元环的三萜类化合物及其生理上可接受的盐或衍生物组成的组。
• FEEDS AND FERTILIZERS CONTAINING PENTACYCLIC TRITERPENES
  申请人：The Nisshin OilliO, Ltd.

  公开号：EP1430787A1

  公开（公告）日：2004-06-23

  The present invention relates to a feed, a fertilizer, a melanogenesis- inhibitory agent for animals and plants and a blackening/browning-inhibitory composition for animals and plants, each comprising, as an effective component, at least one member selected from the group consisting of pentacyclic triterpenes, physiologically acceptable salts thereof and derivatives thereof, which have an excellent melanogenesis-inhibitory effect.

  本发明涉及一种饲料、一种肥料、一种动植物黑色素生成抑制剂和一种动植物变黑/褐变抑制组合物，其中每一种都包含至少一种选自五环三萜类化合物、其生理上可接受的盐类及其衍生物组成的组的有效成分，它们具有极佳的黑色素生成抑制效果。