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Synthesis of thiazolyl-N-phenylmorpholine Derivatives and their Biological Activities

[ Vol. 17 , Issue. 7 ]

Author(s):

Amerah M. Al-Soliemy, Thoraya A. Farghaly*, Eman M. H. Abbas, Mohamed R. Shaaban*, Mohie E. M. Zayed and Tarek B. A. El-Naggar   Pages 790 - 805 ( 16 )

Abstract:


Background: Morpholine and thiazole rings are two heterocycles which are wellknown with a wide spectrum of different biological activities, especially antitumor activity.

Objective: 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.

Methods: 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.

Results: Mass, 1H NMR, 13C 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.

Conclusion: We have succeeded to synthesize a series of N-phenylmorpholine derivatives pendant to thiazole moiety as antitumor agents.

Keywords:

Thiosemicarbazones, morpholine, hydrazonoyl chlorides, thiazoles, α-halocarbonyls, anticancer.

Affiliation:

Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah Almukkarramah, 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, Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah B.O.208203, 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



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