SYNTHESIS AND PROPERTIES OF MESOIONIC PYRIMIDO[1,2-B]PYRIDAZINE-2,4-DIONES AND MESOIONIC PYRIDAZINO[2,3-A]-S-TRIAZINE-2,4-DIONES - MESOIONIC ANALOGS STRUCTURALLY RELATED TO FERVENULIN

被引:16
作者
COBURN, RA [1 ]
CARAPELLOTTI, RA [1 ]
机构
[1] SUNY BUFFALO, SCH PHARM, DEPT MED CHEM, BUFFALO, NY 14214 USA
关键词
D O I
10.1002/jps.2600651022
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Derivatives of 2 new and unusual classes of heterocycles, possessing structural similarities to the broad spectrum antibiotic fervenulin, were synthesized and examined for in vitro antimicrobial activity. Only 3 of 17 mesoionic pyrimido[1,2-b]pyridazine-2,4-diones exhibited evidence of antimicrobial activity while 7 of 8 mesoionic pyridazino[2,3-a]-s-triazine-2,4-diones were active against 1 or more microorganisms [Serratia marcescens, Staphylococcus aureus, S. epidermidis, Candida albicans, Plasmodium berghei]. Susceptibility toward attack by nucleophiles of both mesoionic pyridazino[2,3-a]-s-triazine-2,4-diones and fervenulin was observed.
引用
收藏
页码:1505 / 1510
页数:6
相关论文
共 11 条
[1]   MESOIONIC PURINONE ANALOGS .7. INVITRO ANTIBACTERIAL ACTIVITY OF MESOIONIC 1,3,4-THIADIAZOLO[3,2-ALPHA]PYRIMIDINE-5,7-DIONES [J].
COBURN, RA ;
GLENNON, RA .
JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (09) :1025-1027
[2]   MESOIONIC PURINONE ANALOGS .4. SYNTHESIS AND IN-VITRO ANTIBACTERIAL PROPERTIES OF MESOIONIC "THIAZOLO[3,2-A]PYRIMIDIN-5,7-DIONES AND MESOIONIC 1,3,4-THIADIAZOLO[3,2-A]PYRIMIDIN-5,7-DIONES [J].
COBURN, RA ;
GLENNON, RA .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1973, 62 (11) :1785-1789
[3]   MESOIONIC PURINONE ANALOGS .3. SYNTHESIS AND PROPERTIES OF MESOIONIC THIAZOLO[3,2-A] PYRIMIDINE-5,7-DIONES [J].
COBURN, RA ;
GLENNON, RA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1973, 10 (04) :487-494
[4]  
DEBOER C, 1959, ANTIBIOT ANNU, P220
[5]  
EBLE TE, 1959, ANTIBIOT ANNU, P227
[6]   THE TAUTOMERISM AND METHYLATION OF 3,6-DISUBSTITUTED PYRIDAZINES [J].
FUJISAKA, M ;
UENO, Y ;
SHINOHARA, H ;
IMOTO, E .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1964, 37 (08) :1107-1113
[7]   2,4,7-TRIAMINO-6-ORTHO-SUBSTITUTED ARYLPTERIDINES . A NEW SERIES OF POTENT ANTIMALARIAL AGENTS [J].
OSDENE, TS ;
RUSSELL, PB ;
RANE, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (03) :431-&
[8]  
RELYEA DI, 1963, Patent No. 636313
[9]   REACTION OF OXALYL CHLORIDE WITH AMIDES .4. SYNTHESIS OF ACYL ISOCYANATES [J].
SPEZIALE, AJ ;
SMITH, LR ;
FEDDER, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4306-&
[10]  
TANABE K, 1963, TAKEDA KENKYUSHO NEM, V22, P133