Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide.

The synthesis of four novel compounds, (i) [(11-{[2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]amino}-11-oxoundecyl)sulfanyl]acetic acid (4), (ii) N-[5-methyl-2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]undec-10-enamide (5), (iii) 2-[(11-{[5-methyl-2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]amino}-11-oxoundecyl)sulfanyl]propanoic acid (6) and (iv) 3-[(11-{[2-(3-nitrophenyl)-4-oxo-1,3-thiazinan-3-yl]amino}-11-oxoundecenyl) sulfanyl]propanoic acid (8) from 10-undecenoic acid hydrazide (1) via m-nitrobenzaldehyde-10-undecenohydrazone (2) using mercaptoacetic acid in (i), 2-mercaptopropionic acid in (ii and iii) and 3-mercaptopropionic acid in (iv) is described. The uncyclized products, ({11-[(2E)-2-(3-nitrobenzylidene)hydrazino]-11-oxo-undecyl}sulfanyl)acetic acid (3) and 3-({11-[(2E)-2-(3-nitrobenzylidene)hydrazino]-11-oxoundecyl}sulfanyl)propanoic acid (7) are also obtained in (i) and (iv), respectively. The hydrazones (2), (3) and (7) exist in two conformers as synperiplanar and antiperiplanar.

Bifunctional derivative of p,p'-dichlorochalcone. Part III. Synthesis and study for cytotoxic activity of a new compound, 2-[2,2-bis(4-chlorophenyl)ethyl]-2-(4-chlorophenyl)-thiazolidin-4-one from p,p'-dichlorochalcone.

The synthesis of 2-(2,2-bis(4-chlorophenyl)ethyl]-2-(4-chlorophenyl)-thiazolidin-4-one (3) from p,p'-dichlorochalcone (1) via 1,3,3-tris(4-chlorophenyl)-propan-1-one (2) using thioglycollic acid in the presence of ammonium carbonate is described. Structural assignment, stereochemistry and biological assay are discussed.