Synthesis of Ursolic Phosphonate Derivatives as Potential Anti-HIV Agents

Deng, Shenglou; Baglin, Isabelle; Nour, Mohammed; Флехтер, О. Б.; Vita, Claudio; Cavé, Christian

doi:10.1080/10426500601088838

Cited by 42 publications

(11 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several α-aminophosphonate derivatives are bioactive. They display antiviral, antimicrobial, antifungal, and antitumor activities [1][2][3][4][5][6][7]. At the same time, we noticed that phosphorus-containing heterocyclic systems also possess a wide range of biological and pharmacological activities [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Ali

Halacheva

2009

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Ali

Halacheva

2009

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

“…Aminophosphonic acid and aminophosphonates of potential medical importance. (A) AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptor antagonist [15]; (B) antimicrobial aminophosphonate [16]; (C) anti-HIV agent [17]; (D) cytotoxic agent against human cervical carcinoma [18].…”

Section: Introductionmentioning

confidence: 99%

Octahydroquinoxalin-2(1H)-One-Based Aminophosphonic Acids and Their Derivatives—Biological Activity towards Cancer Cells

et al. 2020

View full text Add to dashboard Cite

In the search for new antitumor agents, aminophosphonic acids and their derivatives based on octahydroquinoxalin-2(1H)-one scaffold were obtained and their cytotoxic properties and a mechanism of action were evaluated. Phosphonic acid and phosphonate moieties increased the antiproliferative activity in comparison to phenolic Mannich bases previously reported. Most of the obtained compounds revealed a strong antiproliferative effect against leukemia cell line (MV-4-11) with simultaneous low cytotoxicity against normal cell line (mouse fibroblasts-BALB/3T3). The most active compound was diphenyl-[(1R,6R)-3-oxo-2,5-diazabicyclo[4.4.0]dec-4-yl]phosphonate. Preliminary evaluation of the mechanism of action showed the proapoptotic effect associated with caspase 3/7 induction.

show abstract

“…α-Aminophosphonic acids are structural bioisosteres of amino acids displaying a wide range of biological properties and applications in many areas ranging from agrochemistry to medicine [ 1 , 2 , 3 , 4 ]. Some of their varied applications include antitumor agents [ 5 , 6 , 7 ], potent antibiotics [ 8 , 9 ], as antibacterial agents [ 10 , 11 ], antiviral [ 12 ], and enzyme inhibitors [ 13 , 14 , 15 ] such as renin [ 14 , 16 ], or HIV protease [ 17 , 18 ], among others. Joined with their structural similarity to natural carboxylic acids, the intriguing properties of α-aminophosphonic acids also stem from the fact that the tetrahedral geometry of phosphonic acid functionality resembles in a stable manner the high-energy transition state of peptide bond hydrolysis [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells

et al. 2020

View full text Add to dashboard Cite

This work reports a straightforward regioselective synthetic methodology to prepare α-aminophosphine oxides and phosphonates through the addition of oxygen and sulfur nucleophiles to the C–N double bond of 2H-azirine derivatives. Determined by the nature of the nucleophile, different α-aminophosphorus compounds may be obtained. For instance, aliphatic alcohols such as methanol or ethanol afford α-aminophosphine oxide and phosphonate acetals after N–C3 ring opening of the intermediate aziridine. However, addition of 2,2,2-trifluoroethanol, phenols, substituted benzenthiols or ethanethiol to 2H-azirine phosphine oxides or phosphonates yields allylic α-aminophosphine oxides and phosphonates in good to high general yields. In some cases, the intermediate aziridine attained by the nucleophilic addition of O- or S-nucleophiles to the starting 2H-azirine may be isolated and characterized before ring opening. Additionally, the cytotoxic effect on cell lines derived from human lung adenocarcinoma (A549) and non-malignant cells (MCR-5) was also screened. Some α-aminophosphorus derivatives exhibited very good activity against the A549 cell line in vitro. Furthermore, selectivity towards cancer cell (A549) over non-malignant cells (MCR-5) has been detected in almost all compounds tested.

show abstract

Synthesis of Ursolic Phosphonate Derivatives as Potential Anti-HIV Agents

Cited by 42 publications

References 26 publications

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Octahydroquinoxalin-2(1H)-One-Based Aminophosphonic Acids and Their Derivatives—Biological Activity towards Cancer Cells

Synthesis of α-Aminophosphonic Acid Derivatives Through the Addition of O- and S-Nucleophiles to 2H-Azirines and Their Antiproliferative Effect on A549 Human Lung Adenocarcinoma Cells

Contact Info

Product

Resources

About