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 | 57498-76-7

• 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: 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
• 中文别名: 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；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
• 英文名称: 2α,3β-diacetoxyurs-12-en-28-oic acid
• 英文别名: (1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-diacetyloxy-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
• CAS: 57498-76-7
• 化学式: C₃₄H₅₂O₆
• 分子量: 556.783
• InChiKey: LHSSNRACHZBMIY-JPEWKLRBSA-N

物化性质

• 沸点：
  607.2±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 在 甲醇 、 氢氧化钾 作用下， 反应 2.0h， 生成 科罗索酸
  参考文献：
  名称：

  Insulin secretion potentiator

  摘要：

  该发明提供了一种早期胰岛素分泌刺激剂，包括苹果酸等。该发明的早期胰岛素分泌刺激剂能够在餐后立即快速诱导胰岛素分泌，而不会在没有血糖增加的情况下诱导胰岛素分泌。

  公开号：

  US20050137259A1
• 作为产物：
  描述：

  科罗索酸 、 乙酸酐 在 吡啶 作用下， 生成 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：

  五环三萜羧酸衍生物整合哌嗪-氨基酸复合物在体外抑制α-葡萄糖苷酶

  摘要：

  通过在母体化合物的 C-28 位点偶联l-氨基酸的哌嗪复合物，已经制备了 18 种五环三萜羧酸衍生物（山楂酸、科罗索酸和亚洲酸）。在体外评估了原始衍生物的 α-葡萄糖苷酶抑制活性。结果表明，部分化合物（15e IC 50  = 591 μM，16e IC 50  = 423  μM）在乙醇-水体系中的抑制活性与参比阿卡波糖（IC 50 = 347 μM）接近。此外，化合物16e (IC 50  = 380 μM) 显示出比阿卡波糖 (IC50  = 493 μM) 在以 DMSO 作为溶剂的测量系统中。两种不同溶剂体系的比较表明，该衍生物在DMSO体系中比在乙醇-水体系中具有更好的α-葡萄糖苷酶抑制活性。遗憾的是，所有合成的衍生物在两种测试溶剂系统中都表现出比母体化合物更差的 α-葡萄糖苷酶抑制活性。此外，酶动力学结果表明化合物16e的抑制机制为非竞争性抑制，抑制常数K i  = 552 μM。

  DOI：

  10.1016/j.bioorg.2021.105212

文献信息

• Semi-synthesis of C28-modified triterpene acid derivatives from maslinic acid or corosolic acid as potential α-glucosidase inhibitors
  作者：Xiaoqin Liu、Xufeng Zang、Xiaoli Yin、Wuying Yang、Jinxiang Huang、Jianping Huang、Chunxian Yu、Chunshan Ke、Yanping Hong

  DOI：10.1016/j.bioorg.2020.103694

  日期：2020.4

  Combining two bioactive moieties by covalent bond into a novel single hybrid biological entity in view of the principle of active splicing, twenty-two C28-modified derivatives of pentacyclic dihydroxytriterpene carboxylic acids with saturated nitrogen heterocycle segments (i.e. 1-deoxynojirimycin or piperazines) have been synthesized. The inhibitory activities of all final target compounds on α-glucosidase

  鉴于活性剪接的原理，通过共价键将两个生物活性部分结合成一个新的单一杂种生物实体，已经有二十二个具有饱和氮杂环链段的五环二羟基三萜羧酸的C28修饰衍生物（即1-脱氧野oji霉素或哌嗪）。合成的。在体外评估了所有最终靶标化合物对α-葡萄糖苷酶的抑制活性。α-葡萄糖苷酶抑制试验的结果表明，某些衍生物（例如4b：IC50 = 1468.4 µM； 12b：IC50 = 499.6 µM 12c：IC50 = 768.5 µM，13c：IC50 = 819.2 µM）显示出比α-葡萄糖苷酶更好的抑制活性。化合物12b（IC50 = 499）的前体山梨酸（IC50 = 2540.6 µM）或椰油酸（IC50 = 1363.7 µM）6 µM）具有比阿卡波糖（IC50 = 606 µM）更强的抑制活性。另外，酶动力学研究的结果表明，化合物12b的抑制机理是非竞争性抑制，并且抑制常数Ki为570μM。通过
• Pentacyclic triterpenes. Part 5: Synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases
  作者：Xiaoan Wen、Jun Xia、Keguang Cheng、Liying Zhang、Pu Zhang、Jun Liu、Luyong Zhang、Peizhou Ni、Hongbin Sun

  DOI：10.1016/j.bmcl.2007.08.057

  日期：2007.11

  The synthesis and biological evaluation of corosolic acid derivatives and related compounds as inhibitors of rabbit muscle glycogen phosphorylase a is described. Within this series of compounds, 8 (IC(50)=7.31 microM), 12d (IC(50)=3.26 microM), and 12e (IC(50)=5.1 microM) exhibited more potent activities than the parent compound 1 (IC(50)=20 microM). SAR of these compounds is also discussed.

  描述了作为兔肌肉糖原磷酸化酶α抑制剂的钴酸衍生物和相关化合物的合成和生物学评估。在这一系列化合物中，8（IC（50）= 7.31 microM），12d（IC（50）= 3.26 microM）和12e（IC（50）= 5.1 microM）表现出比母体化合物1（IC （50）= 20 microM）。还讨论了这些化合物的SAR。
• [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。
• Synthesis of water soluble pentacyclic dihydroxyterpene carboxylic acid derivatives coupled amino acids and their inhibition activities on α-glucosidase
  作者：Zhen Zeng、Xiaoli Yin、Xueyuan Wang、Wuying Yang、Xiaoqin Liu、Yanping Hong

  DOI：10.1016/j.bioorg.2019.02.001

  日期：2019.5

  Twenty maslinic acid and corosolic acid derivatives were obtained by coupling with L-amino acids at C-28 position. The alpha-glucosidase inhibitory activities of the present compounds were evaluated in vitro. Results reveal that some of the derivatives exhibit a better a-glucosidase inhibitory activity than that of acarbose in the test conditions of ethanol-water solution and DMSO. It is worth noting that maslinic acid and corosolic acid derivatives coupled aspartic acid (9f: IC50 = 382 mu m and 10f: IC50 = 364 mu m, respectively) have the best water solubility and thus presented higher inhibitory activity than that of acarbose (IC50 = 484 mu m). Unfortunately, all of the derivatives possess lower inhibitory properties of a-glucosidase than those of the parent compounds in the measurement system of DMSO solution, even if the derivatives exhibit better water solubility than that of the parent compounds.
• Dinda, Biswanath; De Shiho Arima, Utpal Chandra; Sato, Nariko, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 8, p. 1735 - 1739
  作者：Dinda, Biswanath、De Shiho Arima, Utpal Chandra、Sato, Nariko、Harigaya, Yoshihiro

  DOI：——

  日期：——