(2alpha,3beta)-乌苏-12-烯-2,3,28-三醇 | 4547-28-8

• 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
• 中文名称: (2alpha,3beta)-乌苏-12-烯-2,3,28-三醇
• 英文名称: 2α,3β,28-trihydroxyurs-12-ene
• 英文别名: urs-12-ene-2α,3β,28-triol；corosolinol；Urs-12-en-2α,3β,28-triol；(2R,3R,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-2,3-diol
• CAS: 4547-28-8
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: SDEFNGUXVNFYCG-SYXQBTMUSA-N

物化性质

• 熔点：
  235-240 °C
• 沸点：
  539.9±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2alpha,3beta)-乌苏-12-烯-2,3,28-三醇 在 戴斯-马丁氧化剂 、 碳酸氢钠 、 sodium thiosulfate 作用下， 以 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 2.0h， 生成 corosolinal
  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
• 作为产物：
  描述：

  科罗索酸 在 lithium aluminium tetrahydride 作用下， 生成 (2alpha,3beta)-乌苏-12-烯-2,3,28-三醇
  参考文献：
  名称：

  玫瑰湾柳草的三萜成分

  摘要：

  玫瑰湾柳草（Chamaenerion angustifolium）的叶子显示含有熊果酸，齐墩果酸，山梨酸和迄今未知的酸2α-羟基熊果酸。描述了新酸的部分合成，并将其一些衍生物与异构山梨酸的相应衍生物进行了比较。

  DOI：

  10.1039/j39670000510

文献信息

• ACCELERATOR FOR INITIAL INSULIN SECRETION
  申请人：Use-Techno Corporation

  公开号：EP1674089A1

  公开（公告）日：2006-06-28

  The present invention provides an early insulin secretion stimulator consisting of a triterpene represented by the following general formula (1) and/or a triterpene represented by the following general formula (2). [where R1 represents COOH, etc., R11 and R12 represent CH2OH, etc., X1 represents hydrogen or OH and X11, X12, X21 and X22 represent OH, etc.]

  本发明提供了一种早期胰岛素分泌刺激剂，由以下通式（1）代表的三萜和/或以下通式（2）代表的三萜组成。 [其中 R1 代表 COOH 等，R11 和 R12 代表 CH2OH 等，X1 代表氢或 OH，X11、X12、X21 和 X22 代表 OH 等。］
• Insulin secretion potentiator
  申请人：Matsuyama Futoshi

  公开号：US20050143464A1

  公开（公告）日：2005-06-30

  The present invention provides early insulin secretion stimulators consisting of triterpenes represented by the following general formula (1) and/or triterpenes represented by the following general formula (2). [where R 1 represents COOH, etc., R 11 and R 12 represent CH 2 OH, etc., X 1 represents hydrogen or OH and X 11 , X 12 , X 21 and X 22 represent OH, etc.]
• [EN] GLUCONEOGENESIS INHIBITING AGENT<br/>[FR] AGENTS D'INHIBITION DE LA GLUCONEOGENESE
  申请人：USE TECHNO CORP

  公开号：WO2006054370A1

  公开（公告）日：2006-05-26

  [EN] The present invention provides a gluconeogenesis inhibiting agent containing as an active ingredient corosolic acid, an analogous compound of corosolic acid, or a pharmaceutically acceptable salt thereof.
  [FR] La présente invention concerne un agent d'inhibition de la gluconéogenèse, contenant en tant qu'ingrédient actif de l'acide corosolique, un analogue de l'acide corosolique ou l'un de leurs sels pharmaceutiquement acceptables.
• [EN] NOVEL STRUCTURAL ANALOGS OF COROSOLIC ACID HAVING ANTI-DIABETIC AND ANTI-INFLAMMATORY PROPERTIES<br/>[FR] NOUVEAUX ANALOGUES STRUCTURAUX D'ACIDE COROSOLIQUE PRESENTANT DES PROPRIETES ANTI-DIABETIQUE ET ANTI-INFLAMMATOIRES
  申请人：GOKARAJU GANGA RAJU

  公开号：WO2006006178A1

  公开（公告）日：2006-01-19

  This invention relates to novel corosolic acid analogs of the formula I, wherein R1, R2, R3, R4 and R5 are as indicated below in each of said analogs: 1. R1 = COCH3, R2= R3=R4= H, R5= COOH or 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 & R2 = S02, 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 & R4 = 0, R5= COOCH3 16. R1= R2= COCH3, R3 & R4 = 0, R5= COOCH3 17. R1= R2= H, R3 & R4 = 0, R5= COOH 18. R1= R2= COCH3, R3 & R4 = 0, R5= COOH 19. R1 & R2 = S02, R3 & R4 = 0, R5= COOH 20. R1= R2= H, R3 & 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 & R5= OCO. These compounds exhibit good hypoglycemic and 5-lipoxygenase inhibitory activities. They also inhibit tumour growth. Pharmaceutical compositions containing known adjutants and the title compound are also within the scope of this invention.

  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。
• Triterpenoid constituents of rose-bay willow-herb
  作者：A. T. Glen、W. Lawrie、J. McLean、M. El-Garby Younes

  DOI：10.1039/j39670000510

  日期：——

  The leaves of rose-bay willow-herb (Chamaenerion angustifolium) are shown to contain ursolic acid, oleanolic acid, maslinic acid, and a hitherto unknown acid, 2α-hydroxyursolic acid. A partial synthesis of the new acid is described and some of its derivatives are compared with the corresponding derivatives of the isomeric maslinic acid.

  玫瑰湾柳草（Chamaenerion angustifolium）的叶子显示含有熊果酸，齐墩果酸，山梨酸和迄今未知的酸2α-羟基熊果酸。描述了新酸的部分合成，并将其一些衍生物与异构山梨酸的相应衍生物进行了比较。