Synthesis and biological evaluation of simplified mycothiazole analogues

• Published in: Bioorganic & medicinal chemistry letters Vol. 16; no. 5; pp. 1309 - 1311
• Main Authors: Mahler, Graciela, Serra, Gloria, Dematteis, Sylvia, Saldaña, Jenny, Domínguez, Laura, Manta, Eduardo
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.03.2006; Elsevier
• Subjects: Animals; Anthelmintic; Anthelmintics - chemical synthesis; Anthelmintics - chemistry; Anthelmintics - pharmacology; Anthelmintics - toxicity; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antineoplastic agents; Antiparasitic agents; Biological and medical sciences; Cell Line, Tumor; Deoxo-Fluor; General aspects; HTC-15 colon cells; Larva - drug effects; Medical sciences; Molecular Structure; Mycothiazole; Nematoda; Nippostrongylus - drug effects; Nippostrongylus brasiliensis; Oxazolines; Oxazolone - analogs & derivatives; Oxazolone - chemical synthesis; Oxazolone - chemistry; Pharmacology. Drug treatments; Structure-Activity Relationship; Thiazoles - chemical synthesis; Thiazoles - chemistry; Thiazoles - pharmacology; Thiazoles - toxicity; Thiazolines; Anthelmintic; HTC-15 colon cells; Mycothiazole; Deoxo-Fluor; Thiazolines; Oxazolines; Antineoplastic agent; Five membered ring; Thiazole derivatives; Cytotoxicity; Organic carbamate; Nippostrongylus brasiliensis; Structure activity relation; Colon; Secondary alcohol; Chemical synthesis; Nematoda; Oxazole derivatives; Tumor cell; Oxygen nitrogen heterocycle; Human; Sulfur nitrogen heterocycle; Aliphatic compound; In vitro; Cell line; Larva; Helmintha; Parasiticide; Nemathelminthia; Invertebrata; Ethylenic compound
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2005.11.072

New structurally mycothiazole analogues were synthesized and evaluated against HCT-15 colon tumor cells and L 4 larvae of Nippostrongylus brasiliensis. Thiazoline and oxazoline analogues of the natural product mycothiazole were synthesized from a common intermediate and evaluated in vitro against HCT-15 colon cancer cells and L 4 larvae of nematode Nippostrongylus brasiliensis. The nature of the heterocyclic moiety seems to modulate the cytotoxic or anthelmintic activity.