diacetylcorosolyl chloride | 873677-08-8

• 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
• 英文名称: diacetylcorosolyl chloride
• CAS: 873677-08-8
• 化学式: C₃₄H₅₁ClO₅
• 分子量: 575.229
• InChiKey: RLBMSQJSWSIBFU-JPEWKLRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.88
• 重原子数：
  40.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diacetylcorosolyl chloride 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-[2-(2α,3β-dihydroxy-urs-12-en-28-aminocarbonyl)]ethylpiperazine
  参考文献：
  名称：

  由山楂酸或椰油酸半合成C28修饰的三萜酸衍生物，作为潜在的α-葡萄糖苷酶抑制剂。

  摘要：

  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

  DOI：

  10.1016/j.bioorg.2020.103694
• 作为产物：
  描述：

  积雪草酸 在 吡啶 、 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 diacetylcorosolyl chloride
  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

• [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。
• 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.