Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase

被引:103
作者
Chen, J
Liu, J
Zhang, LY
Wu, GZ
Hua, WY
Wu, XM
Sun, HB
机构
[1] China Pharmaceut Univ, Coll Pharm, Ctr Drug Discovery, Nanjing 210009, Peoples R China
[2] China Pharmaceut Univ, Jiangsu Ctr Drug Screening, Nanjing 210038, Peoples R China
[3] China Pharmaceut Univ, Coll Pharm, Dept Pharmacol, Nanjing 210009, Peoples R China
关键词
oleanolic acid; glycogen phosphorylase; inhibitor; derivatives; diabetes;
D O I
10.1016/j.bmcl.2006.03.009
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Oleanolic acid and its synthetic derivatives have been identified as novel inhibitors of glycogen phosphorylase. Within this series of compounds, 4 (IC50 = 3.3 mu M) is the most potent GPa inhibitor. Preliminary structure-activity relationships of the oleanolic acid derivatives are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2915 / 2919
页数:5
相关论文
共 28 条
[1]  
Bradley SE, 2005, World Patent Application, Patent No. [WO2005085245, 2005085245]
[2]   Kinetic and crystallographic studies on 2-(β-D-glucopyranosyl)-5-methyl-1,3,4-oxadiazole, -benzothiazole, and -benzimidazole, inhibitors of muscle glycogen phosphorylase b.: Evidence for a new binding site [J].
Chrysina, ED ;
Kosmopoulou, MN ;
Tiraidis, C ;
Kardakaris, R ;
Bischler, N ;
Leonidas, DD ;
Hadady, Z ;
Somsak, L ;
Docsa, T ;
Gergely, P ;
Oikonomakos, NG .
PROTEIN SCIENCE, 2005, 14 (04) :873-888
[3]   KINETIC MECHANISM OF PHOSPHORYLASE-A .1. INITIAL VELOCITY STUDIES [J].
ENGERS, HD ;
SHECHOSKY, S ;
MADSEN, NB .
CANADIAN JOURNAL OF BIOCHEMISTRY, 1970, 48 (07) :746-+
[4]   FR258900, a novel glycogen phosphorylase inhibitor isolated from Fungus No 138354 Taxonomy, fermentation, isolation and biological activities [J].
Furukawa, S ;
Tsurumi, Y ;
Murakami, K ;
Nakanishi, T ;
Ohsumi, K ;
Hashimoto, M ;
Nishikawa, M ;
Takase, S ;
Nakayama, O ;
Hino, M .
JOURNAL OF ANTIBIOTICS, 2005, 58 (08) :497-502
[5]   Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase [J].
Györgydeák, Z ;
Hadady, Z ;
Felföldi, N ;
Krakomperger, A ;
Nagy, V ;
Tóth, M ;
Brunyánszki, A ;
Docsa, T ;
Gergely, P ;
Somsák, L .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4861-4870
[6]   Effects of oleanolic acid and ursolic acid on inhibiting tumor growth and enhancing the recovery of hematopoietic system postirradiation in mice [J].
Hsu, HY ;
Yang, JJ ;
Lin, CC .
CANCER LETTERS, 1997, 111 (1-2) :7-13
[7]   Inhibition of cytochrome P450 2E1 expression by oleanolic acid: hepatoprotective effects against carbon tetrachloride-induced hepatic injury [J].
Jeong, HG .
TOXICOLOGY LETTERS, 1999, 105 (03) :215-222
[8]   Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids [J].
Kashiwada, Y ;
Wang, HK ;
Nagao, T ;
Kitanaka, S ;
Yasuda, I ;
Fujioka, T ;
Yamagishi, T ;
Cosentino, LM ;
Kozuka, M ;
Okabe, K ;
Ikeshiro, Y ;
Hu, CQ ;
Yeh, E ;
Lee, KH .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (09) :1090-1095
[9]   Potential drug targets and progress towards pharmacologic inhibition of hepatic glucose production [J].
Kurukulasuriya, R ;
Link, JT ;
Madar, DJ ;
Pei, Z ;
Richards, SJ ;
Rohde, JJ ;
Souers, AJ ;
Szczepankiewicz, BG .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (02) :123-153
[10]  
LIU J, 1995, J PHARMACOL EXP THER, V275, P768