Izvorni znanstveni članak

https://doi.org/10.5562/cca3279

Synthesis of New Azoles and Azolopyrimidines Incorporating Morpholine Moiety as Potent Anti-Tumor Agents

Sobhi M. Gomha ; Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
Zeinab A. Muhammad ; Department of Organic Chemistry, National Organization for Drug Control and Research (NODCAR), Giza 12311, Egypt
Hassan M. Abdel-aziz ; Department of Chemistry, Faculty of Science, Bani Suef University, Bani Suef, Egypt
Elham Ezz El-Arab ; Department of Organic Chemistry, National Organization for Drug Control and Research (NODCAR), Giza 12311, Egypt

Sažetak

A new series of morpholinyl-chalcones 2a–d was prepared by reaction of 2-oxo-N,4-diarylbut-3-enehydrazonoyl chlorides 1a–d with morpholine. These chalcones were used as a building block for constructing pyrazoles 3a–d and 3,4-dihydropyrimidine-2(1H)-thione 6 via their reaction with phenylhydrazine and thiourea, respectively. Moreover, a new series of azolopyrimidine derivatives 11a,b, 15, 17, 19, and 21 incorporating morpholine moiety were synthesized by reaction of 1-morpholino-4-phenyl-1-(2-phenylhydrazono)but-3-en-2-one (2a) with a number of heterocyclic amines in the presence of a catalytic amount of acetic acid. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data and the mechanisms of their formation were also discussed. All the synthesized compounds were tested for in vitro activities against two antitumor cell lines, human lung cancer (A-549) and human hepatocellular carcinoma (HepG-2) compared with the employed standard antitumor drug (cisplatin) and the results revealed that compounds 6, 8c and 17 have promising activities compared with cisplatin.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi

hydrazonoyl halides; chalcones; pyrazoles; pyrimidines; anticancer activity

Hrčak ID:

197637

URI

https://hrcak.srce.hr/197637

Datum izdavanja:

2.1.2018.

Posjeta: 1.136 *