A convenient synthesis of 1-ethoxymethyl-5-nitro-6-substituted uracils

被引：11

作者：

Benhida, R

Aubertin, AM

Grierson, DS

Monneret, C

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

[2] INST CURIE,DEPT CHEM,F-75005 PARIS,FRANCE

[3] UNIV STRASBOURG 1,INST VIROL,F-67000 STRASBOURG,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 07期

关键词：

5-nitro-6-aryl uracils; HEPT analogs; HIV-1;

D O I：

10.1016/0040-4039(95)02368-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new and versatile synthetic methods for preparing 5-nitro-analogues of HEPT and MKC-442 which are HIV-1 reverse transcriptase inhibitors, are reported. In both cases the key-step is based upon the displacement of a 6-methylthio or a 6-tosyl group by nucleophiles according an addition-elimination type mechanism.

引用

页码：1031 / 1034

页数：4

共 16 条

[1] BALZARINI J, 1993, MOL PHARMACOL, V44, P694
[2] ISOLATION OF A T-LYMPHOTROPIC RETROVIRUS FROM A PATIENT AT RISK FOR ACQUIRED IMMUNE-DEFICIENCY SYNDROME (AIDS)
BARRESINOUSSI, F
CHERMANN, JC
REY, F
NUGEYRE, MT
CHAMARET, S
GRUEST, J
DAUGUET, C
AXLERBLIN, C
VEZINETBRUN, F
ROUZIOUX, C
ROZENBAUM, W
MONTAGNIER, L
[J]. SCIENCE, 1983, 220 (4599) : 868 - 871
[3] HIV INHIBITORS TARGETED AT THE REVERSE-TRANSCRIPTASE
DECLERCQ, E
[J]. AIDS RESEARCH AND HUMAN RETROVIRUSES, 1992, 8 (02) : 119 - 137
[4] A NEW SERIES OF PYRIDINONE DERIVATIVES AS POTENT NONNUCLEOSIDE HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 SPECIFIC REVERSE-TRANSCRIPTASE INHIBITORS
DOLLE, V
FAN, E
NGUYEN, CH
AUBERTIN, AM
KIRN, A
ANDREOLA, ML
JAMIESON, G
TARRAGOLITVAK, L
BISAGNI, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (23) : 4679 - 4686
[5] THE EFFICACY OF AZIDOTHYMIDINE (AZT) IN THE TREATMENT OF PATIENTS WITH AIDS AND AIDS-RELATED COMPLEX - A DOUBLE-BLIND, PLACEBO-CONTROLLED TRIAL
FISCHL, MA
RICHMAN, DD
GRIECO, MH
GOTTLIEB, MS
VOLBERDING, PA
LASKIN, OL
LEEDOM, JM
GROOPMAN, JE
MILDVAN, D
SCHOOLEY, RT
JACKSON, GG
DURACK, DT
KING, D
[J]. NEW ENGLAND JOURNAL OF MEDICINE, 1987, 317 (04) : 185 - 191
[6] FREQUENT DETECTION AND ISOLATION OF CYTOPATHIC RETROVIRUSES (HTLV-III) FROM PATIENTS WITH AIDS AND AT RISK FOR AIDS
GALLO, RC
SALAHUDDIN, SZ
POPOVIC, M
SHEARER, GM
KAPLAN, M
HAYNES, BF
PALKER, TJ
REDFIELD, R
OLESKE, J
SAFAI, B
WHITE, G
FOSTER, P
MARKHAM, PD
[J]. SCIENCE, 1984, 224 (4648) : 500 - 503
[7] PYRIDINONE DERIVATIVES - SPECIFIC HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 REVERSE-TRANSCRIPTASE INHIBITORS WITH ANTIVIRAL ACTIVITY
GOLDMAN, ME
NUNBERG, JH
OBRIEN, JA
QUINTERO, JC
SCHLEIF, WA
FREUND, KF
GAUL, SL
SAARI, WS
WAI, JS
HOFFMAN, JM
ANDERSON, PS
HUPE, DJ
EMINI, EA
STERN, AM
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (15) : 6863 - 6867
[8] 2',3'-DIDEOXYINOSINE (DDI) IN PATIENTS WITH THE ACQUIRED-IMMUNODEFICIENCY-SYNDROME OR AIDS-RELATED COMPLEX - A PHASE-I TRIAL
LAMBERT, JS
SEIDLIN, M
REICHMAN, RC
PLANK, CS
LAVERTY, M
MORSE, GD
KNUPP, C
MCLAREN, C
PETTINELLI, C
VALENTINE, FT
DOLIN, R
[J]. NEW ENGLAND JOURNAL OF MEDICINE, 1990, 322 (19) : 1333 - 1340
[9] A NOVEL LEAD FOR SPECIFIC ANTI-HIV-1 AGENTS - 1-[(2-HYDROXYETHOXY)METHYL]-6-(PHENYLTHIO)THYMINE
MIYASAKA, T
TANAKA, H
BABA, M
HAYAKAWA, H
WALKER, RT
BALZARINI, J
DECLERCQ, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (12) : 2507 - 2509
[10] SYNTHESIS OF NUCLEOSIDES .3. A GENERAL SYNTHESIS OF PYRIMIDINE NUCLEOSIDES
NIEDBALLA, U
VORBRUGGEN, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (06) : 461 - +

← 1 2 →