Synthesis, Antifungal and Antitumor Activity of Novel (Z)-5-Hetarylmethylidene-1,3-thiazol-4-ones and (Z)-5-Ethylidene-1,3-thiazol-4-ones

Molecules

Alberto Insuasty³  Juan Ramírez³  Marcela Raimondi²  Carlos Echeverry³  Jairo Quiroga³  Rodrigo Abonia³  Manuel Nogueras¹  Justo Cobo¹  Mar໚ Victoria Rodríguez²  Susana A. Zacchino² 

[1] Department of Inorganic and Organic Chemistry, Universidad de Jaén, 23071, Jaén, Spain;Pharmacognosy, Faculty of Biochemical and Pharmaceutical Sciences, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, Argentina;Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, A.A. 25360, Cali, Colombia

关键词: antifungal activity;    antitumor activity;    hetarylmethylidenerhodanine derivatives;    piperidine;    morpholine;   

DOI  :  10.3390/molecules18055482

来源: mdpi

【 摘 要 】

New hetaryl- and alkylidenerhodanine derivatives 3a–d, 3e, and 4a–d were prepared from heterocyclic aldehydes 1a–d or acetaldehyde 1e. The treatment of several rhodanine derivatives 3a–d and 3e with piperidine or morpholine in THF under reflux, afforded (Z)-5-(hetarylmethylidene)-2-(piperidin-1-yl)thiazol-4(5H)-ones and 2-morpholinothiazol-4(5H)-ones 5a–d, 6a–d, and (Z)-5-ethylidene-2-morpholinothiazol-4(5H)-one (5e), respectively, in good yields. Structures of all compounds were determined by IR, 1D and 2D NMR and mass spectrometry. Several of these compounds were screened by the U.S. National Cancer Institute (NCI) to assess their antitumor activity against 60 different human tumor cell lines. Compound 3c showed high activity against HOP-92 (Non-Small Cell Lung Cancer), which was the most sensitive cell line, with GI₅₀ = 0.62 μM and LC₅₀ > 100 μM from the in vitro assays. In vitro antifungal activity of these compounds was also determined against 10 fungal strains. Compound 3e showed activity against all fungal strains tested, but showed high activity against Saccharomyces cerevisiae (MIC 3.9 μg/mL).

【 授权许可】

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© 2013 by the authors; licensee MDPI, Basel, Switzerland.