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

Sobhi M. Gomha 1,* email and Khaled D. Khalil 1,2 email
1 Department of Chemistry, Faculty of Science, University of Cairo, Giza 12613, Egypt 2 Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat13060, Kuwait
* Author to whom correspondence should be addressed.
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 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.
Keywords: thiosemicarbazides; thiazoles; hydrazonoyl halides; ultra-sound irradiation; cytotoxic activity

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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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