Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, Saudi Arabia.
Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Division, National Research Center, 33 El Bohouth St. (former El Tahrir St.) Dokki, Giza, P.O. Box 12622, Egypt.
Med Chem. 2021;17(7):790-805. doi: 10.2174/1573406416666200517103435.
Morpholine and thiazole rings are two heterocycles which are wellknown with a wide spectrum of different biological activities, especially antitumor activity.
The aim of the work is to design and synthesize hybrid heterocyclic compounds of morpholine and thiazole moieties via the reaction of morpholino-thiosemicarbazone derivatives with various α-halocarbonyl compounds and screening their antitumor activity against three tumor cell lines namely, TK-10, MCF-7 and UACC-62.
An efficient synthesis of a series of N-phenylmorpholine derivatives linked with thiazole moiety was accomplished. The reaction of N-subistituted-2-(N-phenylmorpholine)ethylidene) hydrazine- 1-carbothioamide (thiosemicarbazone derivative) with acetyl and ester-hydrazonoyl chlorides, α-chloroketones, or α-bromoesters afforded the corresponding thiazole derivatives pendent to N-phenylmorpholine moiety in good to excellent yields.
Mass, H NMR, C NMR, and elemental analysis were used to confirm the structure of all the new derivatives. The antitumor activities of synthesized N-phenylmorpholine-thiazole derivatives were investigated against three tumor cells namely, TK-10, MCF-7 and UACC-62. The results of such investigation indicated that some derivatives showed good potential to inhibit the growth of the two cells of the tested tumor cells. One of the tested compounds, N-ethyl thiosemicarbazone derivative 7 revealed potent growth inhibition of all the three tumor cells.
We have succeeded to synthesize a series of N-phenylmorpholine derivatives pendant to thiazole moiety as antitumor agents.
吗啉和噻唑环是两种杂环，具有广泛的不同生物活性，特别是抗肿瘤活性。
本工作的目的是通过吗啉代硫代半卡巴腙衍生物与各种α-卤羰基化合物的反应，设计并合成吗啉和噻唑部分的杂环化合物，并筛选其对三种肿瘤细胞系（TK-10、MCF-7 和 UACC-62）的抗肿瘤活性。
高效合成了一系列连接噻唑部分的 N-苯基吗啉衍生物。N-取代-2-（N-苯基吗啉）亚乙基）腙-1-甲硫酰胺（硫代半卡巴腙衍生物）与乙酰基和酯酰肼基氯、α-氯酮或α-溴酯反应，得到相应的噻唑衍生物，收率良好至优秀。
质谱、1H NMR、13C NMR 和元素分析用于确证所有新衍生物的结构。合成的 N-苯基吗啉-噻唑衍生物对三种肿瘤细胞（即 TK-10、MCF-7 和 UACC-62）的抗肿瘤活性进行了研究。研究结果表明，一些衍生物具有抑制两种受试肿瘤细胞生长的良好潜力。其中一种测试化合物，N-乙基硫代半卡巴腙衍生物 7 对所有三种肿瘤细胞均显示出很强的生长抑制作用。
我们成功地合成了一系列作为抗肿瘤剂的连接噻唑部分的 N-苯基吗啉衍生物。
