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

Abstract

Dimethyl 2,6‐dimethyl‐4‐oxo‐4H‐chromen‐3‐yl‐phosphonate (1a) and dimethyl 6‐methyl‐2‐phenyl‐4‐oxo‐4H‐chromen‐3‐yl‐phosphonate (1b) were synthesized and reacted with primary aliphatic amines to yield title compounds 4—6. Their antibacterial properties against Gram‐positive and Gram‐negative bacteria strains were tested by the MIC method. Four of seventeen tested compounds (1d, 3, 4a, and 4b) exhibit detectable activity against S. aureus. Some representative examples of newly synthesized compounds were tested for their alkylating properties in vitro in the Preussmann test. Compounds 1a, 1c, 1d, 3, 5d, and 6a possess highly alkylating activity toward standard derivative 4‐(4'‐nitrobenzyl)pyridine (NBP).

DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

“…The X-ray and spectroscopy analysis, as well as biological activity studies have been carried out for this group of compounds [8][9][10][11][12][13][14][15][16]. The X-ray studies on the interactions in the crystal lattice have showed that the intramolecular hydrogen bond, producing a graph set motif of S6 [17,18], is a common feature of the studied oxaphosphinine derivatives.…”

Structural elucidation of some antimicrobial constituents from the leaf latex of Aloe trigonantha L.C. Leach

“…Aloesin (1) is a chromone while the others are anthrone glycosides. Previous studies have demonstrated that natural chromones isolated from diverse plant species such as Cassia petersiana (Fabaceae) [25], Ferula communis (Apiaceae) [26] and Aloe barbadensis (Asphodelaceae) [27] as well as synthetic phosphonic derivatives of chromones [28] have activity towards Gram-negative and Gram-positive bacteria. Similarly, anthraquinones which are structurally related to anthrones have been shown to inhibit growth of several pathogenic microorganisms [29, 30].…”

Cytotoxic effect, differentiation, inhibition of growth and theoretical calculations of an N,N-donor ligands and its platinum(II), palladium(II) and copper(II) complexes

“…In addition, the structures of 2, 3 and 4 were also confirmed using 1 H NMR spectroscopy in DMSO-d 6 . DMSO was a solvent of choice because of low solubility of ligand 2 and its complexes in other solvents.…”

“…Chromone (benzo-c-pyrone) derivatives constitute another class of biologically important compounds, which display a wide range of biologically relevant properties including anticonvulsant [4], antimicrobial [5,6] and antitumor activities [7][8][9]. The reaction with primary amines on the chromone system, leading to the opening of the c-pyrone ring, is followed by spontaneous cyclisation of the intermediary enamino ketones into coumarin derivatives.…”