SYNTHESIS OF NOVEL 3',4'-SECO ANALOGS OF DIDEHYDRO DIDEOXY NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS

被引：7

作者：

JOKIC, M

SKARIC, V

机构：

[1] Laboratory of Stereochemistry and Natural Products, Department of Organic Chemistry, Biochemistry Ruder Bošković Institute, 41001 Zagreb

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(00)76665-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel acyclo analogues (13,14) of didehydro dideoxy adenosine (d4A) lacking C-3'-C-4' bond were synthesized as potential anti-HIV agents. The key step involves the bromination of unsaturated isomer 6 with NBS in mono protected ethylene glycol leading to 3',4'-seco-2'-bromo-3'-hydroxl compound 11a. Activation of 3'-hydroxy group and reductive elimination of vicinal bromo tosylate gave 13 which on deprotection was converted into the target molecule 14.

引用

页码：2937 / 2940

页数：4

共 17 条

[1] SYNTHESIS OF 1',2'-SECO ANALOGS OF DIDEOXY DIDEHYDRO NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS [J].

AZYMAH, M ;

CHAVIS, C ;

LUCAS, M ;

IMBACH, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1561-1563

[2] A HIGHLY STEREOSELECTIVE SYNTHESIS OF ANTI-HIV 2',3'-DIDEOXYNUCLEOSIDES AND 2',3'-DIDEHYDRO-2',3'-DIDEOXYNUCLEOSIDES [J].

BEACH, JW ;

KIM, HO ;

JEONG, LS ;

NAMPALLI, S ;

ISLAM, Q ;

AHN, SK ;

BABU, JR ;

CHU, CK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3887-3894

[3]

BLANK HU, 1970, LIEBIGS ANN CHEM, V742, P34

[4] SELENIUM NUCLEOPHILES FOR THE PREPARATION OF ANTIVIRAL NUCLEOSIDES [J].

COSFORD, NDP ;

SCHINAZI, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2161-2165

[5]

DeClercq E., 1990, DESIGN ANTIAIDS DRUG

[6] AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].

HURYN, DM ;

OKABE, M .

CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768

[7] STEREOCONTROLLED CONVERSION OF 1-(3-HYDROXYPROP-1-ENYL)URACIL ISOMERS INTO POLYFUNCTIONAL 3,9-PROPANO-AZA-9H-XANTHINES AND 3,9(9,3)-PROPENO-AZA-9H-XANTHINES [J].

JOKIC, M ;

SKARIC, V .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08) :2225-2232

[8] REGIOSPECIFIC AND HIGHLY STEREOSELECTIVE ELECTROPHILIC ADDITION TO FURANOID GLYCALS - SYNTHESIS OF PHOSPHONATE NUCLEOTIDE ANALOGS WITH POTENT ACTIVITY AGAINST HIV [J].

KIM, CU ;

LUH, BY ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2642-2647

[9] SYNTHESES OF THE ANTI-AIDS DRUG 2',3'-DIDEOXYCYTIDINE FROM CYTIDINE [J].

MANCHAND, PS ;

BELICA, PS ;

HOLMAN, MJ ;

HUANG, TN ;

MAEHR, H ;

TAM, SYK ;

YANG, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3473-3478

[10] PREPARATION OF 1-(2,3-DIDEOXY-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE (D4T)1 AND 2',3'-DIDEOXYADENOSINE (DDA) - GENERAL-METHODS FOR THE SYNTHESIS OF 2',3'-OLEFINIC AND 2',3'-DIDEOXY NUCLEOSIDE ANALOGS ACTIVE AGAINST HIV [J].

MANSURI, MM ;

STARRETT, JE ;

WOS, JA ;

TORTOLANI, DR ;

BRODFUEHRER, PR ;

HOWELL, HG ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (20) :4780-4785

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