The Synthesis of Chromone-3-Methanephosphonic Acid and Chromone-2-Methanephosphonic Acid

Kostka, Krzysztof; Modranka, Roman

doi:10.1080/10426509108038860

Cited by 19 publications

(5 citation statements)

References 8 publications

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“…The phosphonate 78 has been obtained by refluxing an equimolar mixture of 1, P(OPh) 3 and H 2 NCO 2 CH 2 Ph in glacial AcOH [70]. Reaction of 76 (R = Me) with HBr in AcOH gives 79 that can be reduced by red P -HI in hot HOAc to 80 [67]. 3-Formylchromone 1 can be crystallised from methanol; on prolonged (22-25 hr) heating in dry methanol under reflux, however, undergoes complete acetalisation.…”

Section: Nov-dec 2008mentioning

confidence: 99%

Chemistry and application of 4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

Ghosh

Patra

2008

Journal of Heterocyclic Chem

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Section: Nov-dec 2008mentioning

confidence: 99%

Chemistry and application of 4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

Ghosh

Patra

2008

Journal of Heterocyclic Chem

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“…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] .…”

Section: Introductionmentioning

confidence: 99%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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

Budzisz

Nawrot

Małecka

2001

Arch. Pharm. Pharm. Med. Chem.

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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).

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“…Thus, many chromone derivatives substituted with phosphonic acid residue have been synthesized. 3 Phosphorobenzopyrane and phosphorocoumarine derivatives are of interest by their high-level alkylation properties in vitro in Preussmann test with 4-͑4Ј-nitrobenzyl͒ pyridine ͑NBP͒ ͑Ref. 4͒ and because of their expected strong activity in vivo.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular forces and conformational change upon crystallization: The case of phosphorobenzopyrane derivatives

Rybarczyk‐Pirek

Zgierski

2001

The Journal of Chemical Physics

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Study on the conformational equilibrium of the alanine dipeptide in water solution by using the averaged solvent electrostatic potential from molecular dynamics methodology J. Chem. Phys. 135, 194502 (2011); 10.1063/1.3658857 Vibrational absorption, vibrational circular dichroism, and theoretical studies of methyl lactate self-aggregation and methyl lactate-methanol intermolecular interactionsThe possible conformations of two phosphorobenzopyrane derivatives ͑I and II͒ are investigated with the help of ab initio and density functional theory methods. Special attention is paid to the conformation around the phosphine group. It is demonstrated that while I possesses the same conformations in the gas and crystal phases, II assumes a conformation in a crystal that is not the lowest energy conformer in the isolated molecule. The effect is explained by the difference in the crystal packing of benzopyrane rings for the two compounds. The higher energy conformer of II is favored in a crystal since it avoids creation of strong repulsive interaction between neighboring molecules due to short interatomic distances.

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The Synthesis of Chromone-3-Methanephosphonic Acid and Chromone-2-Methanephosphonic Acid

Cited by 19 publications

References 8 publications

Chemistry and application of 4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

Chemistry and application of 4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

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

Intermolecular forces and conformational change upon crystallization: The case of phosphorobenzopyrane derivatives

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