naa a22 4500 510733840 CHVBK 20180411083002.0 cr unu---uuuuu 180411e20131101xx s 000 0 eng 10.1007/s12039-013-0496-5 doi (NATIONALLICENCE)springer-10.1007/s12039-013-0496-5 Chemistry of phosphorus ylides 31: Reaction of azidocoumarin with active phosphonium ylides, synthesis and antitumour activities of chromenones [Elektronische Daten] [SOHER MAIGALI, MANSOURA ABD-EL-MAKSOUD, FOUAD SOLIMAN] 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. Graphical Abstract When the azidochromenone was allowed to react with active phosphacumulenes, it gave triazol-, triazepin-, aziridin-, and pyrrolchromenone derivatives. Furthermore, the reaction of azide towards Phosphallene ylide was, investigated. The newly synthesized compounds were screened for their in vitro cytotoxic and growth inhibitory activities against, human breast and liver carcinoma cell lines. Indian Academy of Sciences, 2013 Phosphacumulenes nationallicence phosphallene ylide nationallicence triazoles nationallicence triazepines nationallicence triazine-phosphanylidenes and antitumour activity nationallicence MAIGALI SOHER Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt aut ABD-EL-MAKSOUD MANSOURA Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt aut SOLIMAN FOUAD Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt aut Journal of Chemical Sciences Springer India 125/6(2013-11-01), 1419-1428 0974-3626 125:6<1419 2013 125 12039 https://doi.org/10.1007/s12039-013-0496-5 text/html Onlinezugriff via DOI 1 brief-communication jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s12039-013-0496-5 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- MAIGALI SOHER Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt aut NATIONALLICENCE 700 1- ABD-EL-MAKSOUD MANSOURA Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt aut NATIONALLICENCE 700 1- SOLIMAN FOUAD Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki, Cairo, Egypt aut NATIONALLICENCE 773 0- Journal of Chemical Sciences Springer India 125/6(2013-11-01), 1419-1428 0974-3626 125:6<1419 2013 125 12039 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer