Synthesis and antimicrobial testing of some new S-substituted-thiopyridines, thienopyridines, pyridothienopyrimidines and pyridothienotriazines.
The reaction of 5-acetyl-4-aryl-3-cyano-6-methylpyridine-2(1H)-thiones (1a, b) with 4-methylphenacyl bromide, chloro-N-arylacetamides or chloroacetonitrile gave the corresponding S-substituted thiopyridines 2a-c, 4a-f and 6a-c, respectively. The latter compounds underwent intramolecular Thorpe-Ziegler cyclization to give 2-substituted 5-acetyl-3-amino-4-aryl-6-methylthieno[2,3-b]pyridines 3a-c, 5a-f and 7a-c. Compounds 5a-f and 7b, c are key intermediates in the synthesis of the target compounds. Some compounds showed remarkable antimicrobial activity.
Abdel-Rahman
A E
AE
Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt.
Bakhite
E A
EA
Al-Taifi
E A
EA
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001232:Aspergillus fumigatus / Q000187:drug effects; D001409:Bacillus cereus / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D011506:Proteins / Q000187:drug effects; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects; D014227:Triazines / Q000138:chemical synthesis* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D007202:Indicators and Reagents; D011506:Proteins; D011725:Pyridines; D011743:Pyrimidines; D014227:Triazines