Synthesis and antidiabetic/antioxidant properties of nucleobase-bearing phosphor ester motifs

Abdou, Wafaa M.; Kamel, Azza A.; Shaddy, Abeer A.

doi:10.1007/s00706-017-2034-5

Cited by 4 publications

(2 citation statements)

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“…were been underwent intramolecular group translocation of an alkyl moiety to form the phosphoramidates 5a-c, this in turn, promotes the stability of the resulting compound 5ac [21,29,[39][40][41][42][43]. Whereas the known triazinedione 6 was formed through cyclization of azide 1 due to the presence of the trialkyl phosphites 2a-c that acted as Lewis base and facilitate formation of the triazine cyclic form 6 [30] (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…The attention in coumarin derivative chemistry and the biological activities of these compounds has increased through the previous five decades. In follow up to our lab research plan that pointed to the utility of phosphorus reagents in pharmaceuticals synthesis [18][19][20][21][22][23][24][25][26][27][28][29], we expand the previous work on phosphor reagents and coumarins [30,31] to produce unprecedented coumarin derivatives of prospective biological activities, particularly as antioxidants. The methodology depends on the reaction of azidochromene carbaldehyde 1 and 4-azidocoumarin (16) with trialkyl phosphites 2a-c, dialkyl phosphites 7a-c, and hexaalkylphosphorus triamides 11a,b.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Coumarin Derivatives Bearing Phosphor Ester Motifs and Evaluation of their Antioxidant Activities

et al. 2020

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phosphoramidate, phosphoranylidenetriazene, and azaphosphole derivatives can be respectively formed when the substituted azidocoumarin 1 reacted with trialkylphosphites (TAP), dialkylphosphonates (DAP), and tris(dialkylamino)phosphines. The known triazinedione was revealed to be a side product in the reactions of carbaldehyde 1 with TAP and tris(dialkylamino)phosphines. In the same context, when the starting coumarin 16 was allowed to react with P (III) reagents, chromen phosphoramidates and chromen phosphoric triamide derivatives were obtained via Staudinger reaction. Contrary to that pathway, phosphoranylidenetriazen chromen derivative could be isolated and identified when coumarin 16 was allowed to react with tris(diethylamino)-phosphine. The antioxidant activities of 6-newly products were evaluated. The results showed that two from the six screened compounds exhibited good antioxidant activities.

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