8-AZA-ANALOGS OF PMEA AND PMEG - SYNTHESIS AND IN-VITRO ANTI-HIV ACTIVITY

被引：14

作者：

FRANCHETTI, P ^{[1
]}

SHEIKHA, GA ^{[1
]}

CAPPELLACCI, L ^{[1
]}

MESSINI, L ^{[1
]}

GRIFANTINI, M ^{[1
]}

LOI, AG ^{[1
]}

DEMONTIS, A ^{[1
]}

SPIGA, MG ^{[1
]}

LACOLLA, P ^{[1
]}

机构：

[1] UNIV CAGLIARI,DIPARTIMENTO BIOL SPERIMENTALE,I-09124 CAGLIARI,ITALY

来源：

NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 08期

关键词：

D O I：

10.1080/15257779408009475

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

8-Aza-analogues of the potent antiviral nucleotide analogues 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) and 9-[2-(phosphonomethoxy)ethyl]guanine (PMEG) were prepared and evaluated for activity against human immunodeficiency viruses. When compared to the parent compounds, 8-aza-PMEA (1) and -PMEG (2) were less cytotoxic for MT-4 cells, but also less potent against HIV-1 and HIV-2. A new synthesis of PMEG starting from guanine is also reported.

引用

页码：1707 / 1719

页数：13

共 15 条

[1] MARKED INVIVO ANTIRETROVIRUS ACTIVITY OF 9-(2-PHOSPHONYLMETHOXY-ETHYL)ADENINE, A SELECTIVE ANTI-HUMAN IMMUNODEFICIENCY VIRUS AGENT [J].

BALZARINI, J ;

NAESENS, L ;

HERDEWIJN, P ;

ROSENBERG, I ;

HOLY, A ;

PAUWELS, R ;

BABA, M ;

JOHNS, DG ;

DECLERCQ, E .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (01) :332-336

[2]

DEA P, 1978, CHEM BIOL NUCLEOSIDE, P301

[3] A NOVEL SELECTIVE BROAD-SPECTRUM ANTI-DNA VIRUS AGENT [J].

DECLERCQ, E ;

HOLY, A ;

ROSENBERG, I ;

SAKUMA, T ;

BALZARINI, J ;

MAUDGAL, PC .

NATURE, 1986, 323 (6087) :464-467

[4] ANALOGS OF 8-AZAGUANOSINE/E [J].

ELLIOTT, RD ;

MONTGOMERY, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (10) :1186-1191

[5] ACYCLIC NUCLEOTIDE ANALOGS .3. SYNTHESIS OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE AND RELATED-COMPOUNDS [J].

HOLY, A ;

ROSENBERG, I .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1987, 52 (11) :2801-2809

[6] ACYCLIC NUCLEOTIDE ANALOGS - SYNTHESIS, ANTIVIRAL ACTIVITY AND INHIBITORY EFFECTS ON SOME CELLULAR AND VIRUS-ENCODED ENZYMES INVITRO [J].

HOLY, A ;

VOTRUBA, I ;

MERTA, A ;

CERNY, J ;

VESELY, J ;

VLACH, J ;

SEDIVA, K ;

ROSENBERG, I ;

OTMAR, M ;

HREBABECKY, H ;

TRAVNICEK, M ;

VONKA, V ;

SNOECK, R ;

DECLERCQ, E .

ANTIVIRAL RESEARCH, 1990, 13 (06) :295-311

[7]

HOLY A, 1989, ACS S SERIES, V401

[8] SYNTHESIS OF 8-AZA-2'-DEOXYADENOSINE AND RELATED 7-AMINO-3H-1,2,3-TRIAZOLO[4,5-D]PYRIMIDINE 2'-DEOXYRIBOFURANOSIDES - STEREOSELECTIVE GLYCOSYLATION VIA THE NUCLEOBASE ANION [J].

KAZIMIERCZUK, Z ;

BINDING, U ;

SEELA, F .

HELVETICA CHIMICA ACTA, 1989, 72 (07) :1527-1536

[9] ACYCLIC PURINE PHOSPHONATE ANALOGS AS ANTIVIRAL AGENTS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

KIM, CU ;

LUH, BY ;

MISCO, PF ;

BRONSON, JJ ;

HITCHCOCK, MJM ;

GHAZZOULI, I ;

MARTIN, JC .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (04) :1207-1213

[10] CHARACTERIZATION OF N7 AND N9 ALKYLATED PURINE ANALOGS BY H-1 AND C-13 NMR [J].

KJELLBERG, J ;

JOHANSSON, NG .

TETRAHEDRON, 1986, 42 (23) :6541-6544

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