Triterpene based compounds with potent anti-maturation activity against HIV-1

被引:20
作者
Gerrish, David [1 ]
Kim, In Chul [1 ]
Kumar, Dange V. [1 ]
Austin, Harry [1 ]
Garrus, Jennifer E. [1 ]
Baichwal, Vijay [1 ]
Saunders, Michael [1 ]
McKinnon, Rena S. [1 ]
Anderson, Mark B. [1 ]
Carlson, Robert [1 ]
Arranz-Plaza, Esther [1 ]
Yager, Kraig M. [1 ]
机构
[1] Myriad Pharmaceut Inc, Salt Lake City, UT 84108 USA
关键词
Betulinic acid; Triterpene; HIV-1; Maturation inhibitor; Anti-viral;
D O I
10.1016/j.bmcl.2008.10.098
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Efforts towards developing orally bioavailable HIV-1 maturation inhibitors starting from betulinic acid 1 are described. SAR resulted in improved potency, physicochemical properties, and enhanced oral absorption in rats. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6971 / 6380
页数:4
相关论文
共 31 条
[1]   Betulinic acid derivatives as HIV-1 antivirals [J].
Aiken, C ;
Chen, CH .
TRENDS IN MOLECULAR MEDICINE, 2005, 11 (01) :31-36
[2]   A Review of Natural and Modified Betulinic, Ursolic and Echinocystic Acid Derivatives as Potential Antitumor and Anti-HIV Agents [J].
Baglin, I. ;
Mitaine-Offer, A. -C. ;
Nour, M. ;
Tan, K. ;
Cave, C. ;
Lacaille-Dubois, M. -A. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2003, 3 (06) :525-539
[3]   Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection [J].
Cichewicz, RH ;
Kouzi, SA .
MEDICINAL RESEARCH REVIEWS, 2004, 24 (01) :90-114
[4]   Betulinic acid derivatives: A new class of human immunodeficiency virus type 1 specific inhibitors with a new mode of action [J].
Evers, M ;
Poujade, C ;
Soler, F ;
Ribeill, Y ;
James, C ;
Lelievre, Y ;
Gueguen, JC ;
Reisdorf, D ;
Morize, I ;
Pauwels, R ;
DeClercq, E ;
Henin, Y ;
Bousseau, A ;
Mayaux, JF ;
LePecq, JB ;
Dereu, N .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) :1056-1068
[5]   ANTI-AIDS AGENTS .11. BETULINIC ACID AND PLATANIC ACID AS ANTI-HIV PRINCIPLES FROM SYZIGIUM-CLAVIFLORUM, AND THE ANTI-HIV ACTIVITY OF STRUCTURALLY RELATED TRITERPENOIDS [J].
FUJIOKA, T ;
KASHIWADA, Y ;
KILKUSKIE, RE ;
COSENTINO, LM ;
BALLAS, LM ;
JIANG, JB ;
JANZEN, WP ;
CHEN, IS ;
LEE, KH .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (02) :243-247
[6]   Role of human immunodeficiency virus (HIV) type 1 envelope in the anti-HIV activity of the betulinic acid derivative IC9564 [J].
Holz-Smith, SL ;
Sun, IC ;
Jin, L ;
Matthews, TJ ;
Lee, KH ;
Chen, CH .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2001, 45 (01) :60-66
[7]   Synthesis and anti-HIV activity of bi-functional betulinic acid derivatives [J].
Huang, L ;
Ho, P ;
Lee, KH ;
Chen, CH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (07) :2279-2289
[8]   Anti-AIDS agents. 48. Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis [J].
Ito, J ;
Chang, FR ;
Wang, HK ;
Park, YK ;
Ikegaki, M ;
Kilgore, N ;
Lee, KH .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (10) :1278-1281
[9]   3,28-di-O-(dimethylsuccinyl)-betulin isomers as anti-HIV agents [J].
Kashiwada, Y ;
Chiyo, J ;
Ikeshiro, Y ;
Nagao, T ;
Okabe, H ;
Cosentino, LM ;
Fowke, K ;
Lee, KH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (02) :183-185
[10]   Anti-AIDS agents 38.: Anti-HIV activity of 3-O-acyl ursolic acid derivatives [J].
Kashiwada, Y ;
Nagao, T ;
Hashimoto, A ;
Ikeshiro, Y ;
Okabe, H ;
Cosentino, LM ;
Lee, KH .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (12) :1619-1622