3-O-[N-(phenylsulfonyl)-carbamoyl-17β-N-(phenylsulfonyl)amide]oleanolic acid | 1520096-25-6

• 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: 3-O-[N-(phenylsulfonyl)-carbamoyl-17β-N-(phenylsulfonyl)amide]oleanolic acid
• 英文别名: [(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(benzenesulfonylcarbamoyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] N-(benzenesulfonyl)carbamate
• CAS: 1520096-25-6
• 化学式: C₄₃H₅₈N₂O₇S₂
• 分子量: 779.075
• InChiKey: QTSPASFAYNABHF-ZVAGFZNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  54
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  齐墩果酸 、 异氰酸苯磺酰酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到3-O-[N-(phenylsulfonyl)-carbamoyl-17β-N-(phenylsulfonyl)amide]oleanolic acid
  参考文献：
  名称：

  Rational design and synthesis of topoisomerase I and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs

  摘要：

  Semisynthetic reactions were conducted on oleanolic acid, a common plant-derived oleanane-type triterpene. Ten rationally designed derivatives of oleanolic acid were synthesized based on docking studies and tested for their topoisomerase I and IIa inhibitory activity. Semisynthetic reactions targeted C-3, C-12, C-13, and C-17. Nine of the synthesized compounds were identified as new compounds. The structures of these compounds were confirmed by spectroscopic methods (1D, 2D NMR and MS). Five oleanolic acid analogues (S2, S3, S5, S7 and S9) showed higher activity than camptothecin (CPT) in the topoisomerase I DNA relaxation assay. Four oleanolic acid analogues (S2, S3, S5 and S6) showed higher activity than etoposide in a topoisomerase II assay. The results indicated that the C12-C13 double bond of the oleanolic acid skeleton is important for the inhibitory activity against both types of topoisomerases, while insertion of a longer chain at either position 3 or 17 increases the activity against topoisomerases by various degrees. Some of the synthesized compounds act as dual inhibitors for both topoisomerase I and IIa. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.034

文献信息

• Rational design and synthesis of topoisomerase I and II inhibitors based on oleanolic acid moiety for new anti-cancer drugs
  作者：Ahmed Ashour、Saleh El-Sharkawy、Mohamed Amer、Fatma Abdel Bar、Yoshinori Katakura、Tomofumi Miyamoto、Nozomi Toyota、Tran Hai Bang、Ryuichiro Kondo、Kuniyoshi Shimizu

  DOI：10.1016/j.bmc.2013.11.034

  日期：2014.1

  Semisynthetic reactions were conducted on oleanolic acid, a common plant-derived oleanane-type triterpene. Ten rationally designed derivatives of oleanolic acid were synthesized based on docking studies and tested for their topoisomerase I and IIa inhibitory activity. Semisynthetic reactions targeted C-3, C-12, C-13, and C-17. Nine of the synthesized compounds were identified as new compounds. The structures of these compounds were confirmed by spectroscopic methods (1D, 2D NMR and MS). Five oleanolic acid analogues (S2, S3, S5, S7 and S9) showed higher activity than camptothecin (CPT) in the topoisomerase I DNA relaxation assay. Four oleanolic acid analogues (S2, S3, S5 and S6) showed higher activity than etoposide in a topoisomerase II assay. The results indicated that the C12-C13 double bond of the oleanolic acid skeleton is important for the inhibitory activity against both types of topoisomerases, while insertion of a longer chain at either position 3 or 17 increases the activity against topoisomerases by various degrees. Some of the synthesized compounds act as dual inhibitors for both topoisomerase I and IIa. (C) 2013 Elsevier Ltd. All rights reserved.