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Synthesis and Fungicidal Activity of Novel 4,4′-Bis(2″ -aryl-5″-methyl/unsubstituted-4″-oxo-thiazolidin-3″-yl) Bibenzyl
Siddiqui, Ibadur R.,Singh, Pravin K.,Singh, Jaya,Singh, Jagdamba
, p. 7062 - 7065 (2007/10/03)
Reduction followed by nitration of benzil I yielded 4,4′- dinitrobibenzyl (III) which by reduction furnished quantitatively and analytically pure 4,4′-diaminobibenzyl (IV) which on condensation with different carbonyl compounds gave 4,4′-bis (benzylideneamino) bibenzyls (Va-f). Compounds (Va-f) on cycloaddition with mercaptoacetic acid/2-mercaptopropionic acid yielded the corresponding 4-oxothiazolidin-3-yl bibenzyls (Vla-I). The compounds VIg-I have two chiral centers in each thiazolidinone moiety so two diastereomers are possible, but on crystallization and repeated chromatography, one diastereomer was obtained. The absolute configuration of the diastereomer was tentatively assigned on the basis of 1H NMR spectra. 1H NMR spectra of the product showed a distinct doublet at δ 1.22 for C5-CH3 of thiazolidinone ring (22, 23) and a distinct quartet at δ4.20 for the C5-H proton. Similarly, the C2 proton showed an independent singlet at δ 5.95, so the diastereomers obtained were assigned trans configuration. Compounds Va-f and Vla-I were evaluated in vitro for their fungitoxicities against Fusarium oxysporium and Penicillium citrinum. All the compounds were found to be antifungal active. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.
