Synthesis, spectral and biological evaluation of some new thiazolidinones and thiazoles based on t-3-alkyl-r-2,c-6-diarylpiperidin-4-ones.
A stereospecific synthesis of some thiazolidinones and thiazoles was achieved conveniently through certain alpha-halo keto agents and reactivity of chloroacetyl chloride was successfully enhanced by CsF-Celite+CH(3)COONa. NMR studies revealed that the configuration of N-N bond is found to be anti with respect to C-3 alkyl group while C=N bond in thiazolidinone is trans with respect to N-N bond. Antimycobacterial activity tested against Mycobacterium tuberculosis indicated that compounds 19, 20, 24, 29, 30 and 32 exhibited twofold enhanced potency than Rifampicin. Similarly, antimicrobial screening studies pointed out that compounds 21 and 28 exceptionally noticed promising activities and particularly, 21 against Staphylococcus aureus and, 24 and 32 against Rhizopus sp. exhibited onefold elevated inhibition potency whereas 21 against Klebsiella pneumoniae showed twofold improved potency than Ciprofloxacin and Amphotericin B.
Aridoss
G
G
Division of Image Science and Information Engineering, Pukyong National University, Nam-Gu, Busan 608 739, South Korea.
Amirthaganesan
S
S
Kim
M S
MS
Kim
J T
JT
Jeong
Yeon Tae
YT
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D013844:Thiazoles; D053778:Thiazolidines