A novel esterification procedure applied to synthesis of biologically active esters of Foscarnet

Gorin, B. I.; Ferguson, Colin G.; Thatcher, Gregory R. J.

doi:10.1016/s0040-4039(97)00491-7

Cited by 20 publications

(15 citation statements)

References 10 publications

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“…This later disease can be diagnosed analyzing carefully from a biopsy the crystal solid deposited in the sample by using different spectroscopic techniques, as reported in the literature [5][6][7][8][9][10][11][12][13]. Hence, the preparations of other derivatives of foscarnet are useful and important to design new drugs with the same biological activities but with fewer side effects [14][15][16][17][18]. Temperini et al [19] have found that foscarnet also can acts as an activator/inhibitor of the metallo enzyme carbonic anhydrase and they have resolved the structure of this adduct by using X-ray diffraction, including the structure of foscarnet.…”

Section: Introductionmentioning

confidence: 99%

Structural and Vibrational Study On the Acid, Hexa-Hydrated and Anhydrous Trisodic Salts of Antiviral Drug Foscarnet

Iramain

Brandán

2018

DDIPIJ

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The structural and vibrational properties of acid species, hexa-hydrated and anhydrous trisodic salts of antiviral drug foscarnet in gas phase and in aqueous solution have been studied in this work by using the hybrid B3LYP method with the 6-31G* and 6-311++G** basis sets. The properties in solution were carried out with the self consistent reaction force (SCRF) method by using the integral equation formalism variant polarised continuum (IEFPCM) and SD models while the complete vibrational assignments for those three species were performed in both media by using the experimental available infrared spectrum of hexa-hydrated trisodic salt and the scaled quantum mechanical force field (SQMFF) methodology. The natural bond orbital (NBO) studies suggest that the hexa-hydrated salt in solution is most stable than the anhydrous one in the same medium but in gas phases the anhydrous salt shows a higher stability in solution. The atoms in molecules (AIM) analyses have revealed the ionic characteristics of the O---Na bonds in both salts supporting the higher stability of the hexa-hydrated salt in solution. The evaluation of the frontier orbitals show that the anhydrous salt is the most reactive species in solution, as supported by its higher solvation energy and volume variation. Apparently, the presences of phosphate group in foscarnet probably increase its activity when it is used as drug. The experimental infrared bands observed in the hexa-hydrated species at 1059 and 983 cm -1 are clearly attributed to the stretching modes of phosphate group while the strong bands at 1445 and 1333 cm -1 are associated to the stretching modes of carboxylate group. In addition, the force constants for the carboxylate and phosphate groups are reported.

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Section: Introductionmentioning

confidence: 99%

Structural and Vibrational Study On the Acid, Hexa-Hydrated and Anhydrous Trisodic Salts of Antiviral Drug Foscarnet

Iramain

Brandán

2018

DDIPIJ

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“…Organophosphorus compounds are ubiquitous in nature, and they have broad applications in the fields of agriculture and medicine [1][2][3][4]. It has been found that 4-H-1,3,2-oxazaphosphoridines derived from 2-amino acids possess fairly high insecticidal activity [5,6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel chiral 2‐oxo‐ and 2‐thio‐1,3,2‐oxazaphospholidines via asymmetric cyclization of L‐methionol with (thio)phosphoryl dichlorides

Liu¹,

Chen²,

Huang³

2005

Heteroatom Chemistry

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“…During the past two decades, ␣-ketophosphonates and their derivatives have attracted considerable attention because these compounds are endowed with special physical, chemical, and pharmacological properties due to the proximity of the carbonyl and the phosphoryl groups [1][2][3][4][5][6][7][8][9][10][11][12]. For example, it is well known that phosphonoformic acid (PFA) is effective in AIDS chemotherapy as an antiviral agent with activity against HIV, HSV, and human cytomegalovirus (HCMV) [13,14]. However, its clinical applications are restricted because of its poor penetration across mucosal or cellular membranes and its by-effect on bones [15,16].…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis and crystal structure of 2‐propyl‐5‐(substituted)phenyl‐1,4‐dioxo‐1,2,3,4,5,6,7,8‐octahydro‐[1,4,2]diazaphosphorino[1,2‐a] [1,3,2]benzodiazaphosphorine 3‐oxides

Huang

Chen

2002

Heteroatom Chemistry

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In order to search for novel antitumor and antiviral agents with high activity and low toxicity, some 2‐propyl‐5‐(substituted)phenyl‐1,4‐dioxo‐1,2,3,4,5,6,7,8‐octahydro‐[1,4,2]diazaphosphorino[1,2‐a][1,3,2]benzodiazaphosphorine 3‐oxides (2a–e) have been designed incorporating the proximate carbonyl and phosphoryl groups into the benzoannulated phosphadiamide heterocycle and synthesized in acceptable yields. These compounds contain the proximate carbonyl and phosphoryl groups in the fused heterocycle. Their structures were confirmed by spectroscopic methods and microanalyses. The results from X‐ray crystallography analysis of 2a showed that the proximate carbonyl and phosphoryl groups are not coplanar because of their being jointly located in the fused heterocycle, having ring tension, and this then destroys the conjugation between the CO and the PO moieties. As a result, the length of the PC bonds measured as 1.851(3)–1.852(3) Å are just the same as that of a PC bond not involved in conjugation (1.80–1.85 Å). Also,the C(1), C(2), C(3), N(2), N(3), and P(1) atoms of the [1,4,2]diazaphosphorino moiety exist preferably in the boat conformation. The coplanar C(1), C(3), N(2), and N(3) atoms, within an average deviation of 0.0102 Å, form the ground floor of the boat conformation, whereas the P(1) and C(2) atoms are on the same side of the coplanar structure with the distance of 0.7067 and 0.6315 Å, respectively. © 2002 John Wiley & Sons, Inc. Heteroatom Chem 13:63–71, 2002; DOI 10.1002/hc.1107

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A novel esterification procedure applied to synthesis of biologically active esters of Foscarnet

Cited by 20 publications

References 10 publications

Structural and Vibrational Study On the Acid, Hexa-Hydrated and Anhydrous Trisodic Salts of Antiviral Drug Foscarnet

Structural and Vibrational Study On the Acid, Hexa-Hydrated and Anhydrous Trisodic Salts of Antiviral Drug Foscarnet

Synthesis of novel chiral 2‐oxo‐ and 2‐thio‐1,3,2‐oxazaphospholidines via asymmetric cyclization of L‐methionol with (thio)phosphoryl dichlorides

Efficient synthesis and crystal structure of 2‐propyl‐5‐(substituted)phenyl‐1,4‐dioxo‐1,2,3,4,5,6,7,8‐octahydro‐[1,4,2]diazaphosphorino[1,2‐a] [1,3,2]benzodiazaphosphorine 3‐oxides

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