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

摘要

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.

材料

产品编号

品牌

产品描述

360481

Sigma-Aldrich

1,4-二氧六环, ACS reagent, ≥99.0%, contains ≤25 ppm BHT as stabilizer

296309

Sigma-Aldrich

1,4-二氧六环, anhydrous, 99.8%, contains <=25 ppm BHT as stabilizer

34857

Sigma-Aldrich

1,4-二氧六环, suitable for HPLC, ≥99.5%

676934

Sigma-Aldrich

1,4-二氧六环, ACS reagent, ≥99.0%, contains <=25 ppm BHT as stabilizer

33147

Sigma-Aldrich

1,4-二氧六环, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5% (GC)

115835

Sigma-Aldrich

2-溴苯乙酮, 98%

D201863

Sigma-Aldrich

1,4-二氧六环, ReagentPlus^®, ≥99%, contains ≤25 ppm BHT as stabilizer

76887

Supelco

1,4-二氧六环, analytical standard

CRM48367

Supelco

1,4-二氧六环溶液, certified reference material, 2000 μg/mL in methanol, ampule of 1 mL

551368

Sigma-Aldrich

1,4-二氧六环溶液, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D)

10905

Sigma-Aldrich

氯丙酮, Wacker Chemie AG, ≥96.0% (GC)

736171

Supelco

1,4-二氧六环溶液, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), NMR tube size 5 mm × 8 in.

77450

Supelco

2-溴苯乙酮, derivatization grade (GC derivatization), LiChropur^™, ≥99.0%

704814

Sigma-Aldrich

1,4-二氧六环溶液, suitable for NMR (reference standard), 10 mM in D₂O ("100%", 99.96 atom % D), NMR tube size 5 mm × 7 in.

684228

Sigma-Aldrich

1,4-二氧六环溶液, suitable for NMR (reference standard), 40% in benzene-d₆ (99.6 atom % D), NMR tube size 10 mm × 8 in.

612073

Sigma-Aldrich

1,4-二氧六环溶液, 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.

611905

Sigma-Aldrich

1,4-二氧六环溶液, 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.

631868

Supelco

1,4-二氧六环溶液, suitable for NMR (reference standard), 5 mM in chloroform-d (99.8 atom % D), NMR tube size 3 mm × 8 in.

631833

Supelco

1,4-二氧六环溶液, suitable for NMR (reference standard), 5 mM in benzene-d₆ (99.6 atom % D), NMR tube size 3 mm × 8 in.