A CONVENIENT SYNTHESIS OF 5-DEAZA NONCLASSICAL ANTIFOLATES - REACTION OF CYANOTHIOACETAMIDE WITH SODIUM-SALTS OF 2-(HYDROXYMETHYLENE)-1-CYCLOALKANONES

被引:51
作者
ELGEMEIE, GEH
HUSSAIN, BAW
机构
[1] Chemistry Department, Faculty of Science, Qatar university, Doha
关键词
D O I
10.1016/S0040-4020(01)80745-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Condensation of cyanothioacetamide with sodium salts of 2-(Hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediates for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.
引用
收藏
页码:199 / 204
页数:6
相关论文
共 14 条
[1]   SYNTHESIS AND ANTIFOLATE PROPERTIES OF 10-ALKYL-5,10-DIDEAZA ANALOGS OF METHOTREXATE AND TETRAHYDROFOLIC ACID [J].
DEGRAW, JI ;
CHRISTIE, PH ;
KISLIUK, RL ;
GAUMONT, Y ;
SIROTNAK, FM .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :673-677
[2]   NOVEL SYNTHESIS OF INDANS, TETRALONES, CONDENSED BENZOCARBOCYCLIC NITRILES AND CONDENSED PYRIDINE-2(1H)-THIONES FROM THE REACTIONS OF CYCLOALKYLIDENE-MALONONITRILES WITH ARYLMETHYLENE(CYANO)-ACETAMIDE AND ARYLMETHYLENE(CYANO)-THIOACETAMIDE [J].
ELGEMEIE, GEH ;
ELZANATE, AM ;
MANSOUR, AK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (08) :1073-1074
[3]   UNEXPECTED PRODUCTS OF THE REACTION OF CYCLOALKYLIDENE(CYANO)THIOACETAMIDES WITH ARYLMETHYLENEMALONONITRILES - A DIFFERENT NOVEL SYNTHETIC ROUTE TO CONDENSED PYRIDINE-2(1H)-THIONES AND CONDENSED CARBOCYCLIC NITRILES [J].
ELGEMEIE, GEH ;
REGAILA, HA ;
SHEHATA, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05) :1267-1270
[4]   REACTIONS WITH 3,5-DIAMINOPYRAZOLES - NEW ROUTES TO PYRAZOLO[1,5-A]PYRIMIDINES [J].
ELGEMEIE, GEH ;
FATHY, NM ;
FADDAH, LM ;
EBEID, MY ;
ELSAID, MK .
ARCHIV DER PHARMAZIE, 1991, 324 (03) :149-152
[5]  
ELGEMEIE GEH, 1992, B CHEM SOC JPN, V65, P2241
[6]  
ELGEMEIE GEH, 1993, IN PRESS SYNTHESIS
[7]   STUDIES ON AMINOAZOLES - SYNTHESIS OF PYRAZOLO[1,5-A]PYRIMIDINES AND THEIR AZA DERIVATIVES [J].
ELGEMEIE, GH ;
ELGHANDOUR, AH ;
ELSHIMY, HM .
JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (03) :466-474
[8]   FOLATE ANTAGONISTS .20. SYNTHESIS AND ANTI-TUMOR AND ANTI-MALARIAL PROPERTIES OF TRIMETREXATE AND RELATED 6-[(PHENYLAMINO)METHYL]-2,4-QUINAZOLINEDIAMINES [J].
ELSLAGER, EF ;
JOHNSON, JL ;
WERBEL, LM .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (12) :1753-1760
[9]  
ENSMINGER WD, 1979, ADV CANCER CHEMOTHER, V1, P61
[10]   SYNTHESIS AND ANTI-TUMOR ACTIVITY OF 2,4-DIAMINO-6-(2,5-DIMETHOXYBENZYL)-5-METHYLPYRIDO[2,3-D]PYRIMIDINE [J].
GRIVSKY, EM ;
LEE, S ;
SIGEL, CW ;
DUCH, DS ;
NICHOL, CA .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (03) :327-329