Microwave synthesis, anti-oxidant and anti-tumor activity of some nucleosides derived 2-oxonicotinonitrile. Issue 24 (17th December 2019)

• Record Type: Journal Article
• Authors: El-Sayed, Hassan A.; Moustafa, Ahmed H.; Hassan, Allam A.; El-Seadawy, Nermin A. M.; Pasha, Sherin H.; Shmiess, Nadia A. M.; Awad, Hanem M.; Hassan, Nasser A.
• Is Part Of: Synthetic communications. Volume 49:Issue 24(2019)
• Page Start: 3465
• Page End: 3474
• Publication Date: 2019-12-17
• Subjects: Acyclic sugars -- anti-cancer activity -- anti-oxidant -- halosugars -- nucleosides -- pyridin-2-(1H)-one-3-carbonitriles; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2019.1672747
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: A facile and convenient synthesis of novel cyclic and acyclic nucleoside derivatives incorporating 2-oxo-1, 2-dihydropyridine-3-carbonitrile moiety has been described. The aglycons 3a, b were coupled with different activated halosugars such as glucosyl, galactosyl, lactosyl bromides and peracetylated ribose, in addition to, acyclic sugar as 4-bromobutylacetate and 2-acetoxyethoxymethyl bromide in basic medium under conventional and microwave irradiation. Deprotection of the synthesized nucleosides was obtained in presence of Et3 N/MeOH and few drops of water. The structures of the synthesized compounds have been deduced from their elemental analyses and spectral data (IR, 1 H NMR, and 13 C NMR). Some of the synthesized compounds were screened as antioxidant and anticancer agents. Good and moderate anticancer activities against HepG-2, PC-3 and HCT116 were observed in vitro for some compounds. GRAPHICAL ABSTRACT: