Synthesis and antifungal activity of some imidazo, pyrazino and v-triazoloquinoxalines.
The reaction of 6,7-diamino-1,4-diethyl-11-quinoxaline-1 H,4H-2,3-dione (1) with aliphatic and aromatic carboxylic acids in the presence and absence of an acid catalyst affords 2-alkyl- and 2-aryl-5,8-diethyl-imidazo[4,5-g]quinoxaline-5 H,8 H-6,7-diones 2a-1. Cyclization of 1 with carbon disulphide in basic medium yields 2-mercapto-5,8-diethyl-imidazo[4,5-g]-quinoxaline-5 H,8 H-6,7-dione (4) which on reactions with methyl iodide and substituted benzyl halides give the S-substituted derivatives 5a-f. Condensation of 1 with 1,2-diketones yields the corresponding pyrazinoquinoxalines 6a-e. v-Triazoloquinoxaline 7 is obtained by cyclization of 1 with nitrous acid. Compounds 2a-1, 5a-f and 6a-3 exhibit moderate to weak antifungal activity.
Abd el-Samii
Z K
ZK
Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Zagazig University, Egypt.
el-Feky
S A
SA
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001231:Aspergillus flavus / Q000187:drug effects; D001234:Aspergillus niger / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003500:Cyclization; D005658:Fungi / Q000187:drug effects*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000935:Antifungal Agents; D007093:Imidazoles; D011719:Pyrazines; D011810:Quinoxalines; D014230:Triazoles