科罗索酸甲酯 | 4518-70-1

• 物质功能分类: 生物化工 - 中草药成分
• 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: 科罗索酸甲酯
• 中文别名: (2alpha,3beta)-2,3-二羟基乌苏-12-烯-28-酸甲酯
• 英文名称: methyl corosolate
• 英文别名: methyl (2α,3β,18β)-2,3-dihydroxy-urs-12-en-28-oate；methyl 2α,3β-dihydroxyurs-12-en-28-oate；methyl 2β-hydroxyursolate；corosolic acid methyl ester；2α,3β-dihydroxy-urs-12-en-28-oic acid methyl ester；2α,3β-Dihydroxy-urs-12-en-28-saeure-methylester；methyl (1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-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-carboxylate
• CAS: 4518-70-1
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: BRZWXKGDPAZBLF-OKUTUCSLSA-N

物化性质

• 熔点：
  211-213 °C(Solv: methanol (67-56-1))
• 沸点：
  545.0±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  科罗索酸甲酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 科罗索酸
  参考文献：
  名称：

  刺槐叶中的三萜皂甙醇：刺槐内酯的结构

  摘要：

  摘要 山楂叶乙醇提取物的酸水解产物与山楂酸和 2α-羟基熊果酸一起提供了一种新的三萜内酯，命名为山楂内酯。通过各种光谱证据、化学转化以及与 ψ-蒲公英甾醇的相关性，已经确定了 careyagenolide 的结构为 2α, 3β-dihydroxytaraxastan-28, 20β-olide。

  DOI：

  10.1016/0031-9422(82)83045-8
• 作为产物：
  描述：

  3-Keto-熊果酸-28-甲酯 在 lead(IV) acetate 、 三氟化硼乙醚 作用下， 以 溶剂黄146 为溶剂， 生成 科罗索酸甲酯
  参考文献：
  名称：

  来自 Melissa officinalis L. 的其他三萜。

  摘要：

  Melissa off. L. 还含有三萜类化合物：梨树酸、三种 2-羟基- 和一种 20- 羟基萜烯酸。桦木酸、桦木脑和三个2-羟基三萜酸存在于根中。2,3-二羟基三萜酸的构型通过齐墩果酸、熊果酸和α-香树脂素的四种异构2-羟基衍生物的合成来证明。

  DOI：

  10.1002/ardp.19743070805

文献信息

• [EN] COMPOUNDS FOR REDUCING GLUCOCORTICOIDS, AND METHODS OF TREATMENT THEREOF<br/>[FR] COMPOSÉS PERMETTANT DE RÉDUIRE LES GLUCOCORTICOÏDES, ET PROCÉDÉS DE TRAITEMENT ASSOCIÉS
  申请人：BIONICHE LIFE SCIENCES INC

  公开号：WO2014071506A1

  公开（公告）日：2014-05-15

  A method for reducing glucocorticoids in an animal in need thereof comprising the use of compounds of the formula (I), wherein the definitions for R', R1-R11 and n are as disclosed in the description. The compounds of formula (I) are for the treatment or prevention of a glucocorticoid-related disorder for maintaining bone density, maintaining and improving the immune system, treating Cushing' s syndrome, treating obesity, improving reproduction efficiency, treating metabolic disorder, treating hypertension, treating hyperglycemia, treating insulin resistance, treating type 2 diabetes, and/or aiding in cancer and immune therapies

  一种用于减少需要动物体内糖皮质激素的方法，包括使用式(I)的化合物，其中R'、R1-R11和n的定义如描述中所披露。式(I)的化合物用于治疗或预防与糖皮质激素相关的疾病，以维持骨密度、维护和改善免疫系统、治疗库欣综合征、治疗肥胖、提高生殖效率、治疗代谢紊乱、治疗高血压、治疗高血糖、治疗胰岛素抵抗、治疗2型糖尿病，和/或在癌症和免疫疗法中发挥作用。
• The cytotoxic principles of Hyptis capitata and the structures of the new triterpenes hyptatic acid-A and -B
  作者：Takashi Yamagishi、De-Cheng Zhang、Jer-Jang Chang、Donald R. McPhail、Andrew T. McPhail、Kuo-Hsiung Lee

  DOI：10.1016/0031-9422(88)80028-1

  日期：1988.1

  methanolic extract of Hyptis capitata has led to the isolation and characterization of five triterpene acids which include the new hyptatic acids -A and -B in addition to the known 2α-hydroxyursolic acid, tormentic acid and maslinic acid. Spectral data in conjunction with X-ray analysis of the methanol solvate of hyptatic acid-A established the structures of these compounds. Hyptatic acid-A and 2α-hydroxyursolic

  摘要 对 Hyptis capita 甲醇提取物的生物测定定向分馏导致了五种三萜酸的分离和表征，除了已知的 2α-羟基熊果酸、tormentic 酸和山楂酸之外，还包括新的 hyptatic酸 -A 和 -B。结合庚酸-A 的甲醇溶剂化物的 X 射线分析的光谱数据确定了这些化合物的结构。Hyptatic acid-A 和 2α-羟基熊果酸在人结肠 HCT-8 肿瘤细胞中显示出显着的体外细胞毒性。
• 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 = CO ，R2 = R3 = R4 = H，R5 = COOH或R1 = R3 = R4 = H，R2 = CO ，R5 = COOH 2. RI = R2 = CO ，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（O ）3，R2 = R3 = R4 = H，R5 = COO 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 = COO 14. R1 = R2 = CO ，R3 = R4 = H，R5 = COO 15. R1 = R2 = H，R3和R4 = 0，R5 = COO 16. R1 = R2 = CO ，R3和R4 = 0，R5 = COO 17. R1 = R2 = H，R3和R4 = 0，R5 = COOH 18. R1 = R2 = CO ，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 = COO 23. R1 = R2 = R3 = R4 = H，R5 = CH20H 24. R1 = R2 = R3 = R4 = H，R5 = CHO 25. R1 = R2 = R3 = R4 = H，R5 = COOCOC6H2（O ）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。