title: A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity.
abstract: Successful implementation of ultrasound irradiation for the rapid synthesis of a novel series of 3-[1-(4-substituted-5-(aryldiazenyl)thiazol-2-yl)hydrazono)ethyl]-2H-chromen-2-ones 5a-h, via reactions of 2-(1-(2-oxo-2H-chromen-3-yl)ethylidene) thiosemicarbazide (2) and the hydrazonoyl halides 3(4), was demonstrated. Also, a new series of 5-arylidene-2-(2-(1-(2-oxo-2H-chromen-3-yl)ethylidene)hydrazinyl)thiazol-4(5H)-ones 10a-d were synthesized from reaction of 2 with chloroacetic acid and different aldehydes. Moreover, reaction of 2-cyano-N'-(1-(2-oxo-2H-chromen-3-yl)ethylidene)-acetohydrazide (12) with substituted benzaldehydes gave the respective arylidene derivatives 13a-c under the conditions employed. The structures of the synthesized compounds were assigned based on elemental analyses and spectral data. Also, the cytototoxic activities of the thiazole derivative 5a was evaluated against HaCaT cells (human keratinocytes). It was found that compound 5a possess potent cytotoxic activity.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Cairo, Giza 12613, Egypt. s.m.gomha@hotmail.com
authors.forename: Sobhi M
authors.initials: SM
authors.lastname: Gomha
authors.forename: Khaled D
authors.initials: KD
authors.lastname: Khalil
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives / Q000737:chemistry; D000098:Acetophenones / Q000737:chemistry; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003374:Coumarins / Q000138:chemical synthesis* / Q000633:toxicity; D004146:Dioxanes / Q000737:chemistry; D055772:Green Chemistry Technology; D006801:Humans; D006835:Hydrazones / Q000737:chemistry; D015603:Keratinocytes / Q000187:drug effects; D012663:Semicarbazides / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013016:Sound; D013844:Thiazoles / Q000138:chemical synthesis* / Q000633:toxicity
chemical_list: D000098:Acetophenones; D003374:Coumarins; D004146:Dioxanes; D006835:Hydrazones; D012663:Semicarbazides; D012997:Solvents; D013844:Thiazoles; D000096:Acetone; C006973:chloroacetone; C013190:phenacyl bromide; C025223:1,4-dioxane