Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone

被引:21
作者
Crosby, Ian T. [1 ]
Rose, Mark L. [1 ]
Collis, Maree P. [2 ]
de Bruyn, Paula J. [1 ]
Keep, Philip L. C. [2 ]
Robertson, Alan D. [2 ]
机构
[1] Monash Univ, Monash Inst Pharmaceut Sci, Parkville, Vic 3052, Australia
[2] AMRAD Operat Pty Ltd, Richmond, Vic 3121, Australia
关键词
D O I
10.1071/CH08177
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity.
引用
收藏
页码:768 / 784
页数:17
相关论文
共 18 条
[1]  
AKIRA I, 1958, YUKI GOSEI KAGAKU KY, V16, P607
[2]   A NEW SYNTHESIS OF THE NAPHTHOPYRAN ANTIBIOTICS [J].
CAMERON, DW ;
CROSBY, IT ;
FEUTRILL, GI .
TETRAHEDRON LETTERS, 1992, 33 (20) :2855-2856
[3]   DICHLORO QUINONES AS DIENOPHILES - SYNTHESIS OF ALIZARIN DERIVATIVES [J].
CAMERON, DW ;
FEUTRILL, GI ;
KEEP, PLC .
TETRAHEDRON LETTERS, 1989, 30 (38) :5173-5176
[4]   NUCLEOPHILIC ALKENES .9. ADDITION OF 1,1-DIMETHOXYETHENE TO AZANAPHTHOQUINONES - SYNTHESIS OF BOSTRYCOIDIN AND 8-O-METHYLBOSTRYCOIDIN [J].
CAMERON, DW ;
DEUTSCHER, KR ;
FEUTRILL, GI .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (07) :1439-1450
[5]  
CANNON J R, 1975, Tetrahedron Letters, V32, P2795
[6]   SYNTHESIS AND CRYSTAL-STRUCTURE OF 7,7A,8,9,11,11A-HEXAHYDRO-7,7,10-TRIMETHYL-1,10-EPOXY-10H-BENZ[DE]ANTHRACEN-6-OL [J].
CANNON, JR ;
MCDONALD, IA ;
SIERAKOWSKI, AF ;
WHITE, AH ;
WILLIS, AC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (01) :57-64
[7]   USEFUL DIENE FOR DIELS-ALDER REACTION [J].
DANISHEFSKY, S ;
KITAHARA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808
[8]   HIV INHIBITORY NATURAL-PRODUCTS .11. STRUCTURE, ABSOLUTE STEREOCHEMISTRY, AND SYNTHESIS OF CONOCURVONE, A POTENT, NOVEL HIV-INHIBITORY NAPHTHOQUINONE TRIMER FROM A CONOSPERMUM SP [J].
DECOSTERD, LA ;
PARSONS, IC ;
GUSTAFSON, KR ;
CARDELLINA, JH ;
MCMAHON, JB ;
CRAGG, GM ;
MURATA, Y ;
PANNELL, LK ;
STEINER, JR ;
CLARDY, J ;
BOYD, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6673-6679
[9]   Regiocontrolled synthesis of the trimeric quinone framework of conocurvone [J].
Emadi, A ;
Harwood, JS ;
Kohanim, S ;
Stagliano, KW .
ORGANIC LETTERS, 2002, 4 (04) :521-524
[10]   HALOGEN DERIVATIVES OF THE 1-4-NAPHTHOQUINONE GROUP AND THE MALEIC ACID SERIES IN THEIR ACTION ON THE MITOSIS OF CHICK FIBROBLASTS [J].
FRIEDMANN, E ;
MARRIAN, DH ;
SIMONREUSS, I .
BIOCHIMICA ET BIOPHYSICA ACTA, 1952, 8 (06) :680-686