Chemistry of phosphorus ylides 31: Reaction of azidocoumarin with active phosphonium ylides, synthesis and antitumour activities of chromenones

Abstract

The reaction of 4-azidochromen-2-one (1) with the nucleophilic phosphacumulene ylides 2, 8, and 12 afforded the new heterocyclic triazoles, triazepines, aziridine, pyrrolone containing a coumarin moiety. Cycloaddition reactions took place first to give triazoline 3 and 9. The triazolines rearranged to the triazepines 4, 10, and 13 accompanied by elimination of triphenylphosphine leading to the phosphorus-free triazepines 5, 11, and moreover, aziridine 6 was produced via nitrogen extrusion from the triazoline 3, followed by ring expansion to the pyrrolone 7. On the other hand, the reaction of the azidocoumarin 1 with the phosphallene yield 15 behaves differently and afforded the triazine 17 and azetone 18. The antitumour activity of compounds 3, 4, 6, and 11 was evaluated, in vitro, against (breast: MCF-7 and liver: HPEG2) human solid tumour cell lines. They showed values closed to that recorded by the reference drug doxorubicin.

Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-carbaldehyde with Phosphacumulene and Phosphaallene Ylides

“…Our continuing interest in the reactions of active phosphacumulene and phosphaallene (hexaphenylcarbodiphosphorane ylide) ylides to prepare carbocyclic and heterocyclic phosphorus compounds of biological interest, [26][27][28][29][30][31] led us to investigate and compare the behaviour of these phosphonium ylides with 4-aminoantipyrine (4-amino-1,5-dimethyl-2-phenyl-1,2dihydropyrazol-3-one-) (1), 4-amino-2-oxo-2H-chromene-3carbaldehyde (9), and 2-chloroquinoline-3-carbaldehyde (12) to synthesise new bioactive phosphorus compounds and their evaluation as antimicrobial agents.…”

Overview on Developed Synthesis Methods of Triazepane Heterocycles

“…Cycloaddition of azide 1 and thiophosphacumulene 12 gave the phosphanylidenetriazepane 11 , while elimination of triphenylphosphine resulted in triazepanone 12 (Scheme ). Moreover, the antitumor activity of these compounds was evaluated in vitro against the breast cancer cell line MCF‐7 and liver HPEG2 human solid tumor cell line (Scheme ) …”

“…Triazepanes are important seven‐membered heterocyclic ring compounds containing three nitrogen atoms. They and their derivatives possess various biological actives such as an antitumor, antimicrobial, antibacterial, and anticancer . In this review, based on the position of the nitrogen atoms in the final triazepine compounds, they are classified as TAP‐1,2,3, TAP‐1,2,4, TAP‐1,2,5, and TAP‐1,3,5, respectively.…”

Chemistry of Phosphorus Ylides. Part 40. Synthesis of Pyrazoles by the [3 + 2] Cycloaddition of Diazo Compounds with Wittig Reagents as Antimicrobial Compounds

“…It was shown that the presence of an azo functionality in many compounds is essential for the exhibition of activity . In addition, the existence of phosphanylidene group also enhanced the biological activity . The present study is focused on the possibility of developing new heterocyclic containing phosphorus moieties with antimicrobial activity.…”