SYNTHESIS OF 3'-DEOXY-3'-(2-PROPYNYL)THYMIDINE AND 3'-CYANOMETHYL-3'-DEOXYTHYMIDINE, ANALOGS OF AZT

被引：60

作者：

FIANDOR, J ^{[1
]}

TAM, SY ^{[1
]}

机构：

[1] HOFFMANN LA ROCHE INC,ROCHE RES CTR,NUTLEY,NJ 07110

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(00)94577-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient procedure using free radical chemistry for introducing a carbon substituent to the 3′-position of 3′-deoxythymidine is described. An application of this procedure to the synthesis of 3′-deoxy-3′-(2-propynyl)thymidine and 3′-cyanomethyl-3′-deoxythymidine, two close analogs of AZT, is presented. © 1990.

引用

页码：597 / 600

页数：4

共 10 条

[1] AZIDOTHYMIDINE - CRYSTAL-STRUCTURE AND POSSIBLE FUNCTIONAL-ROLE OF THE AZIDO GROUP
CAMERMAN, A
MASTROPAOLO, D
CAMERMAN, N
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (23) : 8239 - 8242
[2] STRUCTURE ACTIVITY RELATIONSHIPS OF PYRIMIDINE NUCLEOSIDES AS ANTIVIRAL AGENTS FOR HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 IN PERIPHERAL-BLOOD MONONUCLEAR-CELLS
CHU, CK
SCHINAZI, RF
AHN, MK
ULLAS, GV
GU, ZP
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) : 612 - 617
[3] SYNTHESIS OF PYRIMIDINE 3'-ALLYL-2',3'-DIDEOXYRIBONUCLEOSIDES BY FREE-RADICAL COUPLING
CHU, CK
DOBOSZEWSKI, B
SCHMIDT, W
ULLAS, GV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2767 - 2769
[4] 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
[5] SYNTHESIS AND ANTI-HIV ACTIVITY OF DIFFERENT SUGAR-MODIFIED PYRIMIDINE AND PURINE NUCLEOSIDES
HERDEWIJN, P
BALZARINI, J
BABA, M
PAUWELS, R
VANAERSCHOT, A
JANSSEN, G
DECLERCQ, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (10) : 2040 - 2048
[6] CARBON CARBON BOND FORMATION VIA THE REACTION OF TRIALKYLALLYLSTANNANES WITH ORGANIC HALIDES
KECK, GE
YATES, JB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) : 5829 - 5831
[7] CIRCULATING P24 ANTIGEN LEVELS AND RESPONSES TO DIDEOXYCYTIDINE IN HUMAN IMMUNODEFICIENCY VIRUS (HIV) INFECTIONS - A PHASE-I AND PHASE-II STUDY
MERIGAN, TC
SKOWRON, G
BOZZETTE, SA
RICHMAN, D
UTTAMCHANDANI, R
FISCHL, M
SCHOOLEY, R
HIRSCH, M
SOO, W
PETTINELLI, C
SCHAUMBURG, H
[J]. ANNALS OF INTERNAL MEDICINE, 1989, 110 (03) : 189 - 194
[8] 3'-AZIDO-3'-DEOXYTHYMIDINE (BW A509U) - AN ANTIVIRAL AGENT THAT INHIBITS THE INFECTIVITY AND CYTOPATHIC EFFECT OF HUMAN LYMPHOTROPIC-T VIRUS TYPE-III LYMPHADENOPATHY-ASSOCIATED VIRUS INVITRO
MITSUYA, H
WEINHOLD, KJ
FURMAN, PA
STCLAIR, MH
LEHRMAN, SN
GALLO, RC
BOLOGNESI, D
BARRY, DW
BRODER, S
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1985, 82 (20) : 7096 - 7100
[9] INVIVO ACTIVITY AGAINST HIV AND FAVORABLE TOXICITY PROFILE OF 2',3'-DIDEOXYINOSINE
YARCHOAN, R
MITSUYA, H
THOMAS, RV
PLUDA, JM
HARTMAN, NR
PERNO, CF
MARCZYK, KS
ALLAIN, JP
JOHNS, DG
BRODER, S
[J]. SCIENCE, 1989, 245 (4916) : 412 - 415
[10] YARCHOAN R, 1988, LANCET, V1, P76

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