A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity.

A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity.

Molecules (Basel, Switzerland) (2012-08-07)

Sobhi M Gomha, Khaled D Khalil

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.

MATERIALS

Product Number

Brand

Product Description

684228

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), NMR tube size 10 mm × 8 in.

296309

Sigma-Aldrich

1,4-Dioxane, anhydrous, 99.8%, contains <=25 ppm BHT as stabilizer

612073

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 3 mm × 8 in.

704814

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 10 mM in D₂O ("100%", 99.96 atom % D), NMR tube size 5 mm × 7 in.

611905

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), chromium(III) acetylacetonate 5 mg/mL, NMR tube size 5 mm × 8 in.

76887

Supelco

1,4-Dioxane, analytical standard

551368

Sigma-Aldrich

1,4-Dioxane solution, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D)

CRM48367

Supelco

1,4-Dioxane solution, certified reference material, 2000 μg/mL in methanol, ampule of 1 mL

631868

Supelco

1,4-Dioxane solution, suitable for NMR (reference standard), 5 mM in chloroform-d (99.8 atom % D), NMR tube size 3 mm × 8 in.