title: Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide.
abstract: 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. Structural assignment, stereochemistry and biological assays are discussed.
authors.affiliation: Department of Chemistry, Aligarh Muslim University, Aligarh-202002, India.
authors.forename: V P Mujeebur
authors.initials: VP
authors.lastname: Rahman
authors.forename: Sayeed
authors.initials: S
authors.lastname: Mukhtar
authors.forename: Wajid Husain
authors.initials: WH
authors.lastname: Ansari
authors.forename: Guy
authors.initials: G
authors.lastname: Lemiere
mesh_terms: D000085:Acetates / Q000138:chemical synthesis* / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001681:Biological Assay; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D006835:Hydrazones / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013457:Sulfur Compounds; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: C502285:((11-(2-(3-nitrobenzylidene)hydrazino)-11-oxoundecyl)sulfanyl)acetic acid; C502283:10-undecenoic acid hydrazide; C502284:3-nitrobenzaldehyde-10-undecenohydrazone; D000085:Acetates; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D006834:Hydrazines; D006835:Hydrazones; D009578:Nitrobenzenes; D013457:Sulfur Compounds; D013844:Thiazoles