Design and Synthesis of Oleanolic Acid Rings A and C Lactone Derivatives

被引：2

作者：

Yu, Fei ^{[1
]}

Zheng, Yongxiang ^{[2
]}

Peng, Yiyun ^{[2
]}

Zhou, Demin ^{[2
]}

Xiao, Sulong ^{[2
]}

机构：

[1] Kunming Univ Sci & Technol, Fac Med, Kunming 650500, Peoples R China

[2] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 36卷 / 03期

关键词：

oleanolic acid; Baeyer-Villiger reaction; lactone; OLEANANE-TYPE TRITERPENES; BIOLOGICAL EVALUATION;

D O I：

10.6023/cjoc204509001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oleanolic acid (OA), a naturally occurring triterpene, was found to have a variety of biological and pharmacological properties. To expand its structural diversity, a series of oleanolic acid derivatives, including ring A and/or ring C expansion, were performed via Baeyer-Villiger reaction using m-CPBA and urea-hydrogen peroxide. The structures of all products were characterized by H-1 NMR, C-13 NMR and HRMS.

引用

页码：512 / 519

页数：8

共 15 条

[1] Synthesis and Biological Evaluation of Novel Olean-28, 13β-lactams as Potential Antiprostate Cancer Agents
Ai, Yong
Hu, Yang
Kang, Fenghua
Lai, Yisheng
Jia, Yanju
Huang, Zhangjian
Peng, Sixun
Ji, Hui
Tian, Jide
Zhang, Yihua
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (11) : 4506 - 4520
[2] Design, synthesis, and antihepatocellular carcinoma activity of nitric oxide releasing derivatives of oleanolic acid
Chen, Li
Zhang, Yihua
Kong, Xiangwen
Lan, Edward
Huang, Zhangjian
Peng, Sixun
Kaufman, Daniel L.
Tian, Jide
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) : 4834 - 4838
[3] [丁晔 Ding Ye], 2011, [中国药科大学学报, Journal of China Pharmaceutical University], V42, P385
[4] DDQ-promoted dehydrogenation from natural rigid polycyclic acids or flexible alkyl acids to generate lactones by a radical ion mechanism
Ding, Ye
Huang, Zhangjian
Yin, Jian
Lai, Yisheng
Zhang, Shibo
Zhang, Zhiguo
Fang, Lei
Peng, Sixun
Zhang, Yihua
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (33) : 9495 - 9497
[5] Pharmacological activities of natural triterpenoids and their therapeutic implications
Dzubak, Petr
Hajduch, Marian
Vydra, David
Hustova, Alica
Kvasnica, Miroslav
Biedermann, David
Markova, Lenka
Urban, Milan
Sarek, Jan
[J]. NATURAL PRODUCT REPORTS, 2006, 23 (03) : 394 - 411
[6] Antibacterial activities of a few prepared derivatives of oleanolic acid and of other natural triterpenic compounds
Hichri, F
Ben Jannet, H
Cheriaa, J
Jegham, S
Mighri, Z
[J]. COMPTES RENDUS CHIMIE, 2003, 6 (04) : 473 - 483
[7] Lai Y., 2011, [No title captured], Patent No. [CN102079772A, 102079772, CN 102079772]
[8] Synthesis and Biological Evaluation of Oleanolic Acid Derivatives As Inhibitors of Protein Tyrosine Phosphatase 1B
Qian, Shan
Li, Haijiao
Chen, Yin
Zhang, Weiyu
Yang, Shengyong
Wu, Yong
[J]. JOURNAL OF NATURAL PRODUCTS, 2010, 73 (11): : 1743 - 1750
[9] A biomimetic approach for polyfunctional secocholanes: Tuning flexibility and functionality on peptidic and macrocyclic scaffolds derived from bile acids
Rivera, Daniel G.
Pando, Orlando
Bosch, Rayser
Wessjohann, Ludger A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (16): : 6229 - 6238
[10] Sasaki K., 2001, [No title captured], Patent No. [JP 2001240573, 2001240573]

← 1 2 →