Regioselective synthetic approaches towards 1,2,8,9-tetraazadispiro[4.1.4.2]trideca-2,9-dien-6-ones of potential antimicrobial properties.
Reaction of 2,5-bis(arylmethylidene)cyclopentanones 1a-d with nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2a,b) in 1:2 molar ratio proceeds in a high regioselective manner affording monocycloadducts 3 and dicycloadducts in the form of two isomers 4, 5. Single crystal X-ray diffraction studies of the isolated crystalline form of 3c support the established structure and indicate that the formed product is 7E, 4S, 5R. Antimicrobial activity screening of the synthesized compounds 3-5, utilizing a variety of gram-positive (Staphylococcus aureus, Enterococcus fecalis and Streptococcus agalactiae), gram-negative bacteria (Escherichia coli, Klebsiella pneumoniae and Proteus vulgaris) and yeast (Candida albicans), exhibited that all the prepared analogues acquire promising activities against both gram-positive and gram-negative bacteria especially compounds 3b, 4a (antimicrobial active agents against gram-positive bacteria) and 3c (antimicrobial active agent against gram-negative bacteria).
Girgis
Adel S
AS
Pesticide Chemistry Department, National Research Centre, El-Behoos Street, Dokki, 12622 Cairo, Egypt.
Barsoum
Flora F
FF
Samir
Ahmed
A
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects; D018360:Crystallography, X-Ray; D015195:Drug Design; D013293:Enterococcus faecalis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D011514:Proteus vulgaris / Q000187:drug effects; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013292:Streptococcus agalactiae / Q000187:drug effects; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D011720:Pyrazoles; D013141:Spiro Compounds