Phosphono- and Phosphinolactones in the Life Sciences

Volle, J.‐N.; Guillon, Rémi; Bancel, Frédéric; Békro, Yves-Alain; Pirat, Jean‐Luc; Virieux, David

doi:10.1016/bs.aihch.2015.10.004

Cited by 10 publications

(1 citation statement)

References 136 publications

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“…Organophosphorus compounds have been investigated for applications in agricultural, veterinary, and medicinal applications for decades, and a considerable number of phosphorus-containing drugs have achieved commercial success. , The majority of these approved phosphorus-containing pharmaceuticals contain a phosphate, a phosphoramide, or a phosphonate group, while phosphines, phosphinates, and phosphine oxides are rare. Among the successful examples of organophosphorus drug research are the phosphordiamidate based anticancer drugs cyclophosphamide ( 1 ) and ifosfamide ( 2 ), as well as the phosphonamidate and phosphonate containing reverse transcriptase inhibitors tenofovir alafenamide ( 3 ) and adefovir dipivoxil ( 4 ) to fight infectious diseases like HIV and hepatitis B, respectively (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

2020

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Phosphine oxides and related phosphorus-containing functional groups such as phosphonates and phosphinates are established structural motifs that are still underrepresented in today’s drug discovery projects, and only few examples can be found among approved drugs. In this account, the physicochemical and in vitro properties of phosphine oxides and related phosphorus-containing functional groups are reported and compared to more commonly used structural motifs in drug discovery. Furthermore, the impact on the physicochemical properties of a real drug scaffold is exemplified by a series of phosphorus-containing analogs of imatinib. We demonstrate that phosphine oxides are highly polar functional groups leading to high solubility and metabolic stability but occasionally at the cost of reduced permeability. We conclude that phosphine oxides and related phosphorus-containing functional groups are valuable polar structural elements and that they deserve to be considered as a routine part of every medicinal chemist’s toolbox.

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Section: Introductionmentioning

confidence: 99%

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

2020

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Copper‐Catalyzed α,β‐Regioselective (2+4) Cycloaddition of Propargylic Esters

Zhang,

Wu,

Zhong

et al. 2023

Eur J Org Chem

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A copper‐catalyzed α,β‐regioselective (2+4) cycloaddition of propargylic esters with o‐hydroxyphenyl substituted secondary phosphine oxides (SPOs) was established, which afforded a series of phosphorus‐containing six‐membered heterocycles in high yields (up to 99 % yield). This reaction represents the first α,β‐regioselective (2+n) cycloaddition of propargylic esters via the intermediates of copper−allenylidenes, which will enrich the chemistry of propargylic esters and copper−allenylidenes. Moreover, this work also represents the first application of o‐hydroxyphenyl substituted SPOs as 1,4‐dinucleophiles in (2+4) cycloadditions, which provides a useful protocol for the synthesis of phosphorus‐containing six‐membered heterocycles with potential bioactivity.

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New methods for the synthesis of phosphono-δ-lactones (microreview)

Ceradini

Shubin

2021

Chem Heterocycl Comp

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Phosphono- and Phosphinolactones in the Life Sciences

Cited by 10 publications

References 136 publications

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

Phosphine Oxides from a Medicinal Chemist’s Perspective: Physicochemical and in Vitro Parameters Relevant for Drug Discovery

Copper‐Catalyzed α,β‐Regioselective (2+4) Cycloaddition of Propargylic Esters

New methods for the synthesis of phosphono-δ-lactones (microreview)

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