Department of Chemistry, Faculty of Science, University of Cairo, Giza 12613, Egypt.
Molecules. 2012 Aug 3;17(8):9335-47. doi: 10.3390/molecules17089335.
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.
通过 2-(1-(2-氧代-2H-色烯-3-基)乙基)亚氨基硫代甲脒(2)与腙酰卤 3(4)的反应，成功地实现了超声辐射快速合成一系列新型 3-[1-(4-取代-5-(芳基亚腙基)噻唑-2-基)亚肼基)乙基]-2H-色烯-2-酮 5a-h。此外，还通过 2 与氯乙酸和不同的醛反应，合成了一系列新的 5-芳基亚腙基-2-(2-(1-(2-氧代-2H-色烯-3-基)乙基)腙基)噻唑-4(5H)-酮 10a-d。此外，在所用条件下，2-氰基-N'-(1-(2-氧代-2H-色烯-3-基)乙基)乙二酰肼(12)与取代苯甲醛反应得到相应的芳基亚腙衍生物 13a-c。根据元素分析和光谱数据确定了合成化合物的结构。此外，还评估了噻唑衍生物 5a 对 HaCaT 细胞(人角质形成细胞)的细胞毒性活性。结果发现，化合物 5a 具有很强的细胞毒性活性。
