PHOSPHORYLATION OF NOVEL ORGANOMETALLIC DIHYDRO COUMARIN DERIVATIVES: EVALUATION AS ANTIBACTERIAL AND ANTICANCER

E.A. EL-SAWI¹, M.A. HOSNY², T.M. SAYED^3
1Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, Egypt.
²Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, Egypt.
³Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University, Heliopolis, Cairo, Egypt.

Received : 01-06-2014     Accepted : 24-07-2014     Published : 31-07-2014
Volume : 2     Issue : 1       Pages : 35 - 39
World Res J Org Chem 2.1 (2014):35-39

Keywords : Coumarin, metallation, palladation, phosphorylation, antibacterial, anticancer activity.
Academic Editor : Dr Ali Gharib, S. Srinivas Rao, Ma DL, Mehdi Shahraki, Leung CH, Awatef Mohamed El-Maghraby,
Conflict of Interest : None declared

Coumarin reacted with o-aminothiophenol in ethanol and afforded the tautomeric form of 4(2-mercaptophenylamino) 3, 4-dihydrochromen-2-one, H2L (1). Metallation of compound (1) with Hg(II) and Ni(II) acetate in toluene and drops of acetic acid gave monometallated products [(H2L)Hg(OAc)] (2) and [(H2L)Ni (H2O)2] (3), respectively. However, its reaction with Pd(II) in methanol gave the dimetallated product [Cl(HOMe)Pd(H2L) Pd(HOMe)] (4). Diphosphorylated product C45H36NO2P2 (5) was obtained from the reaction of compound (2) with triphenylphosphine via demercuration. Compound (6) C33H26NO2SPNi with 8-membered ring and compound (7) C51H39NO2SP2PdCl with the loss of palladium atom afforded via phosphorylation of compounds (3) and (4) respectively. The structures of the synthesized products were confirmed by using spectral data: IR, 1H-NMR, MS, thermal analyses and elemental analyses. The new products have exhibited antibacterial activity and compound (7) exhibited excellent anticancer activity.