Synthesis, partition coefficients and antibacterial activity of 3'-phenyl (substituted)-6'-aryl-2' (1H)-cis-3',3'a-dihydrospiro [3-H-indole-3,5'-pyrazolo (3',4'-d)-thiazolo-2-(1H)-ones].
Condensation of isatin with primary aryl amines gave a series of Schiff bases (1) which on reaction with thioglycolic acid in 1,4-dioxane afforded the formation of the corresponding 4- thiazolidinones (2). Compound 2 on condensation with substituted benzaldehydes in anhydrous sodium acetate furnished 3-aryl -5'-phenyl (substituted) spiro [3H-indole-3,2'-thiazolidines]-2-(1H), 4'(5'H)-diones (3). The latter (3) on reaction with hydrazine hydrochloride in anhydrous sodium acetate gave 3'-phenyl (substituted) -6'-aryl-2'(1H)-cis-3',3'a-dihydrospiro [3H-indole-3,5'-pyrazolo (3',4'-d)-thiazolo-2-(1H)-ones] (4). The structure has been established on the basis of spectral data. The partition coefficient for n-octanol/water solvent system and in vitro antibacterial activity of the 2'(1H)-cis-3',3'a-dihydrospiro [3H-indole-3,5'-pyrazolo (3',4'-d)-thiazolo-2-(1H)-one] derivatives have been evaluated.
Sahu
Susant K
SK
University Department of Pharmaceutical Sciences, Utkal University, Vani Vihar. Bhubaneswar-751 004, India. tutu_kh@yahoo.com
Banerjee
Mrityunja
M
Mishra
Sagar K
SK
Mohanta
Raj K
RK
Panda
Prasanna K
PK
Misro
Prafulla K
PK
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021902:Enterobacter aerogenes / Q000187:drug effects / Q000254:growth & development; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007510:Isatin / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D012995:Solubility; D013055:Spectrophotometry, Infrared / Q000379:methods; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013297:Streptococcus pyogenes / Q000187:drug effects / Q000254:growth & development; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D007211:Indoles; D013141:Spiro Compounds; D013844:Thiazoles; D007510:Isatin