3β-acetoxy-2α-hydroxyurs-12-en-28-oic acid

• 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: 3β-acetoxy-2α-hydroxyurs-12-en-28-oic acid
• 英文别名: 3-acetyl-2α-hydroxyursolic acid；3-O-acetylcorosolic acid；(1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-acetyloxy-11-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• 化学式: C₃₂H₅₀O₅
• 分子量: 514.746
• InChiKey: PCEBPJUHBOJBAJ-FXZBVTQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-2α-hydroxyurs-12-en-28-oic acid 、 乙酸酐 在 吡啶 作用下， 反应 10.0h， 以0.6 mg的产率得到2,3-二乙酰氧基科罗索酸; (2alpha,3beta)-2,3-二乙酰氧基乌苏-12-烯-28-酸
  参考文献：
  名称：

  A New Ursane Triterpene from Monochaetum vulcanicum that Inhibits DNA Polymerase β Lyase

  摘要：

  Bioassay-directed fractionation of a butanone extract of Monochaetum vulcanicum resulted in the isolation of a new triterpene (1) and four known compounds, ursolic acid (2), 2alpha-hydroxyursolic acid (3), 34-(p-coumaroyl)ursolic acid (4), and beta-sitosteryl-beta-D-galactoside (5). The structure of the new compound 1 was established as 3beta-acetoxy-2alpha-hydroxyurs-12-en-28-oic acid on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. Compounds 1-3 and 5 exhibited polymerase lyase activity.

  DOI：

  10.1021/np030531b
• 作为产物：
  描述：

  科罗索酸 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 生成 3β-acetoxy-2α-hydroxyurs-12-en-28-oic acid 、 2α,3α-diacetoxyurs-12-en-28-oic acid
  参考文献：
  名称：

  [EN] NOVEL STRUCTURAL ANALOGS OF COROSOLIC ACID HAVING ANTI-DIABETIC AND ANTI-INFLAMMATORY PROPERTIES
  [FR] NOUVEAUX ANALOGUES STRUCTURAUX D'ACIDE COROSOLIQUE PRESENTANT DES PROPRIETES ANTI-DIABETIQUE ET ANTI-INFLAMMATOIRES

  摘要：

  本发明涉及公式I的新型苦瓜酸类似物，其中在每个类似物中R1、R2、R3、R4和R5如下所示：1. R1 = COCH3，R2 = R3 = R4 = H，R5 = COOH或R1 = R3 = R4 = H，R2 = COCH3，R5 = COOH 2. RI = R2 = COCH3，R3 = R4 = H，R5 = COOH 3. R1 = COC5H4N，R2 = R3 = R4 = H，R5 = COOH 4. R1 = COCH2NH2.HCI，R2 = R3 = R4 = H，R5 = COOH 5. R1 = COCH2（CH3）NH2.HCI，R2 = R3 = R4 = H，R5 = COOH 6. R1 = COCH：CHC6H2（OCH3）3，R2 = R3 = R4 = H，R5 = COOCH3 7. R1和R2 = SO2，R3 = R4 = H，R5 = COOH 8. R1 = R2 = R3 = R4 = H，R5 = CONH2 9. RI = R2 = R3 = R4 = H，R5 = CONHC6H5 10. R1 = R2 = R3 = R4 = H，R5 = CONHCH2CH2NH2 11. R1 = R2 = R3 = R4 = H，R5 = CON（CH2CH2）2NH 12. R1 = R2 = R3 = R4 = H，R5 = CONHCH2CH20H 13. R1 = R2 = R3 = R4 = H，R5 = COOCH3 14. R1 = R2 = COCH3，R3 = R4 = H，R5 = COOCH3 15. R1 = R2 = H，R3和R4 = 0，R5 = COOCH3 16. R1 = R2 = COCH3，R3和R4 = 0，R5 = COOCH3 17. R1 = R2 = H，R3和R4 = 0，R5 = COOH 18. R1 = R2 = COCH3，R3和R4 = 0，R5 = COOH 19. R1和R2 = SO2，R3和R4 = 0，R5 = COOH 20. R1 = R2 = H，R3和R4 = 0，R5 = CONH2 21. R1 = R2 = R3 = H，R4 = OH，R5 = CONH2 22. R1 = R2 = R3 = H，R4 = OH，R5 = COOCH3 23. R1 = R2 = R3 = R4 = H，R5 = CH20H 24. R1 = R2 = R3 = R4 = H，R5 = CHO 25. R1 = R2 = R3 = R4 = H，R5 = COOCOC6H2（OCH3）3 26. R1 = R2 = R3 = H，R4和R5 = OCO。这些化合物表现出良好的降血糖和5-脂氧合酶抑制活性。它们也能抑制肿瘤生长。含有已知辅料和本发明的化合物的药物组合物也在本发明的范围内。

  公开号：

  WO2006006178A1

文献信息

• INHIBITING DNA POLYMERASE BETA TO ENHANCE EFFICACY OF ANTICANCER AGENTS
  申请人：Sobol Robert W.

  公开号：US20090081119A1

  公开（公告）日：2009-03-26

  The invention provides anticancer methods. In one embodiment, the inventive method involves the co-administration to cancerous cells of (a) a chemotherapeutic agent, radiation, or a combination of a chemotherapeutic agent and radiation and (b) an inhibitor of DNA polymerase beta. In another embodiment, the invention provides anticancer methods involving the co-administration to cancerous cells of (a) a chemotherapeutic agent, radiation, or a combination of a chemotherapeutic agent and radiation and (b) an siRNA or shRNA in an amount sufficient to attenuate base excision repair within the cell. Another aspect of the invention relates to pharmaceutical compositions comprising an siRNA or shRNA that attenuates base excision repair.
• [EN] INHIBITING DNA POLYMERASE BETA TO ENHANCE EFFICACY OF ANTICANCER AGENTS<br/>[FR] INHIBITION D'ADN POLYMERASE BETA POUR AMELIORER L'EFFICACITE D'AGENTS ANTICANCEREUX
  申请人：UNIV PITTSBURGH

  公开号：WO2007001684A2

  公开（公告）日：2007-01-04

  (EN) The invention provides anticancer methods. In one embodiment, the inventive method involves the co-administration to cancerous cells of (a) a chemotherapeutic agent, radiation, or a combination of a chemotherapeutic agent and radiation and (b) an inhibitor of DNA polymerase beta. In another embodiment, the invention provides anticancer methods involving the co-administration to cancerous cells of (a) a chemotherapeutic agent, radiation, or a combination of a chemotherapeutic agent and radiation and (b) an siRNA or shRNA in an amount sufficient to attenuate base excision repair within the cell. Another aspect of the invention relates to pharmaceutical compositions comprising an siRNA or shRNA that attenuates base excision repair.(FR) La présente invention a trait à des procédés anticancéreux. Dans un mode de réalisation, le procédé de l'invention comprend l'administration conjointe à des cellules cancéreuses (a) d'un agent chimiothérapeutique, d'une radiothérapie, ou d'une combinaison d'agent chimiothérapeutique et de radiothérapie et (b) d'un inhibiteur de l'ADN polymérase bêta. Dans un autre mode de réalisation, l'invention a trait à des procédés anticancéreux comprenant l'administration conjointe aux cellules cancéreuses (a) d'un agent chimiothérapeutique, d'une radiothérapie, ou d'une combinaison d'agent chimiothérapeutique et de radiothérapie et (b) d'un ARNsi ou d'un ARNsh en une quantité suffisante pour atténuer la réparation par excision de base au sein de la cellule. Dans un autre aspect, l'invention a trait à des compositions pharmaceutiques comportant un ARNsi ou ARNsh qui atténue la réparation par excision de base.