Unusual cytotoxicities of 5-(acylethynyl)-1-(2-hydroxyethoxy)methyluracils

被引:26
作者
Kundu, NG [1 ]
Mahanty, JS [1 ]
Spears, CP [1 ]
机构
[1] UNIV SO CALIF,KENNETH NORRIS JR COMPREHENS CANC CTR,CANC RES LAB,LOS ANGELES,CA 90033
关键词
D O I
10.1016/S0960-894X(96)00256-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
5-(Acylethynyl)-1-(2-hydroxyethoxy)methyl uracils (2)-(6) were synthesised in excellent yields from 1-(2-acetoxyethoxy)methyl-5-iodouracil (7) utilising palladium-copper catalysed reactions. Compounds (2)-(5) were shown to be highly active against CCRF-CEM (IC50 0.6-1.6 mu M) and L1210/0 cells (IC50 0.7-2.2 mu M) in culture, and thus exhibit greater activity than their parent bases. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1497 / 1502
页数:6
相关论文
共 22 条
[1]   POTENT AND SELECTIVE-INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 (HIV-1) BY 5-ETHYL-6-PHENYLTHIOURACIL DERIVATIVES THROUGH THEIR INTERACTION WITH THE HIV-1 REVERSE-TRANSCRIPTASE [J].
BABA, M ;
DECLERCQ, E ;
TANAKA, H ;
UBASAWA, M ;
TAKASHIMA, H ;
SEKIYA, K ;
NITTA, I ;
UMEZU, K ;
NAKASHIMA, H ;
MORI, S ;
SHIGETA, S ;
WALKER, RT ;
MIYASAKA, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (06) :2356-2360
[2]   The preparation of acetylenic carbinols [J].
Campbell, KN ;
Campbell, BK ;
Eby, LT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :2882-2884
[3]   HIV-1-SPECIFIC RT INHIBITORS - HIGHLY SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 THAT ARE SPECIFICALLY TARGETED AT THE VIRAL REVERSE-TRANSCRIPTASE [J].
DECLERCQ, E .
MEDICINAL RESEARCH REVIEWS, 1993, 13 (03) :229-258
[4]   ANTIVIRAL CHEMOTHERAPY AND CHEMOPROPHYLAXIS [J].
DOLIN, R .
SCIENCE, 1985, 227 (4692) :1296-1303
[5]   REACTIVITY AND REACTIONS OF AROMATIC ACETYLENIC ACIDS AND KETONES [J].
DREWES, SE ;
DOUGLASS, D ;
MALISSAR, DGS ;
ROOS, GHP ;
KAYE, PT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06) :1507-1511
[6]   SELECTIVITY OF ACTION OF AN ANTI-HERPETIC AGENT, 9-(2-HYDROXYETHOXYMETHYL)GUANINE [J].
ELION, GB ;
FURMAN, PA ;
FYFE, JA ;
DEMIRANDA, P ;
BEAUCHAMP, L ;
SCHAEFFER, HJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1977, 74 (12) :5716-5720
[7]  
Heidelberger C., 1984, PYRIMIDINE PYRIMIDIN, P801, Patent No. 731752
[8]   158 studies in the polyene series - Part VI The preparation of ethinylcarbinols from alpha beta-unsaturated aldehydes [J].
Jones, ERH ;
McCombie, JT .
JOURNAL OF THE CHEMICAL SOCIETY, 1942, :733-735
[9]  
KANG SI, 1987, J MED CHEM, V30, P597
[10]   PYRIMIDINE ACYCLIC NUCLEOSIDES - 1-[(2-HYDROXYETHOXY)METHYL]PYRIMIDINES AS CANDIDATE ANTIVIRALS [J].
KELLEY, JL ;
KELSEY, JE ;
HALL, WR ;
KROCHMAL, MP ;
SCHAEFFER, HJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (06) :753-756