Investigation in the Chromone Series. Part Xx. Chromone-3-Phosphonic Acids and Esters

Synthesis, antimicrobial, and alkylating properties of 3-phosphonic derivatives of chromone

“…31 Cyclo-0.1200 [1,2]oxaphosphinane 4d were prepared as described [11,16] . The IR spectra were recorded on a Pye-Unicam 200G Spectrophotometer in KBr.…”

“…In these studies we determined antibacterial activity of all the new phosphonic acid chromone derivatives, including compounds described in our previous paper [11] . Thus, compounds 1a-d, 3, 4a-d, 5a-d and 6a-d were investigated with regard to their antibacterial activity against standard Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, and against two Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa, the strains of different drug resistance recommended by National Committee for Laboratory Standards (NCCLS) [17] .…”

“…The structure of 1a and 1b was unequivocally confirmed by spectral analysis detailed in Experimental. Compounds 1a and 1b, as well as previously obtained derivatives 1c and 1d [11] , were reacted with primary aliphatic amines i.e. benzylamine, methylamine and ethanolamine, as previously described [16] .…”

“…Fosmidomycin [HCON(OH)-(CH2)3-PO3H2], one of four structurally related phosphonic acid derivatives, isolated from Streptomyces, is the most interesting agent among natural phosphonate antibiotics for use in therapy [6] . Synthesis of such benzo-γ-pyrone derivatives containing phosphonic acid residue was previously presented by us [11] and others [12] . They exhibit diverse biological properties including anticonvulsant [7] , antimicrobiological [8] , and antitumor activities [9] .…”

“…Little is known about the biological activity of new chromone derivatives containing phosphorus [10] . Synthesis of such benzo-γ-pyrone derivatives containing phosphonic acid residue was previously presented by us [11] and others [12] . This paper is a continuation of our research on the derivatives of chromone modified with phosphonic acid residue (1a and 1b), their chemical synthesis and reactions with primary amines, as well the studies on antimicrobial and alkylating properties of the obtained compounds.…”