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Molecules 2012, 17(8), 9335-9347; doi:10.3390/molecules17089335
Article

A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity

1,*  and 1,2
Received: 25 June 2012; in revised form: 18 July 2012 / Accepted: 24 July 2012 / Published: 3 August 2012
(This article belongs to the Section Organic Synthesis)
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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 5ah, 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 10ad 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 13ac 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.
Keywords: thiosemicarbazides; thiazoles; hydrazonoyl halides; ultra-sound irradiation; cytotoxic activity thiosemicarbazides; thiazoles; hydrazonoyl halides; ultra-sound irradiation; cytotoxic activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Gomha, S.M.; Khalil, K.D. A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity. Molecules 2012, 17, 9335-9347.

AMA Style

Gomha SM, Khalil KD. A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity. Molecules. 2012; 17(8):9335-9347.

Chicago/Turabian Style

Gomha, Sobhi M.; Khalil, Khaled D. 2012. "A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity." Molecules 17, no. 8: 9335-9347.



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