Phosphinate-containing heterocycles: A mini-review

Berger, Olivier; Montchamp, Jean‐Luc

doi:10.3762/bjoc.10.67

Cited by 21 publications

(5 citation statements)

References 32 publications

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“…The same phosphinate was also obtained by an intramolecular alkylation [54]. A recent review summarizes the possible syntheses of heterocycles with phosphinate function including phosphole, phosphindole-, oxaphosphole-, phosphorine-and other derivatives, mainly from acyclic phosphinate precursors [67].…”

Section: Scheme 13mentioning

confidence: 99%

Synthesis of Phosphinic Acid Derivatives; Traditional Versus up-to-Date Synthetic Procedures

Keglevich

Kiss²,

Mucsi³

2014

Chem Sci J

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Synthetic methods for the preparation of phosphinic derivatives (esters and amides) are summarized. The basic method is, when phosphinic chlorides are reacted with alcohols or amines. These reactions take place under mild conditions, but utilize expensive chlorides, need a solvent, and a base has to be added to remove the HCl formed. On conventional heating, the phosphinic acids resist undergoing derivatizations by nucleophiles. However, on microwave (MW) irradiation, the phosphinic acids could be esterified by alcohols. The direct esterification does not require an extra solvent, it is atomic efficient, but needs a relatively higher temperature. The similar amidations were reluctant. Phosphinic acids may also be esterified by alkylation that may be promoted by combined phase transfer catalysis and MW irradiation. It is also possible to convert the phosphinic acids by different reagents (e.g. by the T3P  reactant) to a more reactive intermediate that is ready to react with alcohols or amines. Other methods, such as preparation by the Arbuzov reaction or by fragmentation-related phosphorylation are also discussed.

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Section: Scheme 13mentioning

confidence: 99%

Synthesis of Phosphinic Acid Derivatives; Traditional Versus up-to-Date Synthetic Procedures

Keglevich

Kiss²,

Mucsi³

2014

Chem Sci J

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“…Among them, phosphoramide compounds P(O)–N display a broad range of bioactivities and are used as prodrugs of antiviral drugs . In connection with our interest in phosphorus heterocycles, we decided to focus on benzophostam derivatives 1 and 2 (Figure ). Herein, we detail our results, including the first synthesis of the parent 6-membered benzophostam 2b (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of P-Substituted 5- and 6-Membered Benzo-Phostams: 2,3-Dihydro-1H-1,2-benzazaphosphole 2-Oxides and 2,3-Tetrahydro-1H-1,2-benzazaphosphinine 2-Oxides

et al. 2021

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Several approaches were developed for the preparation of phosphorus-substituted 5-and 6-membered benzophostams. Carbodiimide-promoted cyclization of zwitterionic aminophosphinates derived from a nitrobenzene precursor accomplished the cyclization in good yields. Alternatively, a novel copper-catalyzed cross-coupling between a phosphonamide and a bromobenzene precursor produced the heterocycles in moderate to good yields. Three different methods are compared for the synthesis of the P-ethoxy-substituted 5-membered benzophostam.

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“…Nevertheless, the large number of investigations devotet to the chemistry of oxaphosphole derivatives, data of their biological activity is scarce (Berger and Montchamp, 2014;Virieux et al, 2012). Compounds with structural similarity to oxaphospholes are used as antiviral drugs (Tam et al, 2000;Kamiya, 2003;Pescovitz, 2008;Okano, 2009) and anticancer agents (Kanno et al, 2009;Sharabi and Haran-Ghera, 2011).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytostatic Activity of 4-bromo-5-ethyl-2-(ethylamino)- 5-methyl-5H-1,2-oxaphosphole 2-oxide

2018

J App Pharm Sci

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Synthesis of phosphorus heterocycles has gained increasing interest in recent years. Here we wish to report our results on synthesis and on studying of biological activity of 4-bromo-5-ethyl-2-(ethylamino)-5-methyl-5H-1,2-oxaphosphole 2-oxide (Br-oxph-1) using in vivo and in vitro approaches. Br-oxph-1 represents a structural analogue of 4-bromo-2-(diethylamino)-5-ethyl-5-methyl-5H-1,2-oxaphosphole 2-oxide (Br-oxph). Root growth inhibition test using Triticum aestivum L. seeds was provided in order to determine general toxicity of Br-oxph-1. The effective concentration that cause 50% of root length as compared to control was determined -8.23 × 10 3 μM. Cytotoxic potential of Br-oxph-1 (8.23 × 10 3 μM) was evaluated using Allium cepa L.-test. Significant decline in mitotic activity and disturbances of cell cycle kinetics were observed. Further, effects of Br-oxph-1 on human hepatoma cell line SK-HEP-1 in vitro were evaluated by means of cell proliferation assay. The results revealed concentration-dependent and statistically significant inhibitory effect. Concentration of Br-oxph-1 showing 50% reduction in cell proliferation/ viability was 0.642 × 10 3 µM. In conclusion, plant test-systems used in this study revealed growth inhibitory and cytostatic effects of Br-oxph-1. Data in vitro was in accordance with these results. Results of present study revealed stronger cytostatic effect of Br-oxph-1 in comparison with Br-oxph. Obviously, modifications in chemical structure of Br-oxph influence its biological effects.

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Phosphinate-containing heterocycles: A mini-review

Cited by 21 publications

References 32 publications

Synthesis of Phosphinic Acid Derivatives; Traditional Versus up-to-Date Synthetic Procedures

Synthesis of Phosphinic Acid Derivatives; Traditional Versus up-to-Date Synthetic Procedures

Synthesis of P-Substituted 5- and 6-Membered Benzo-Phostams: 2,3-Dihydro-1H-1,2-benzazaphosphole 2-Oxides and 2,3-Tetrahydro-1H-1,2-benzazaphosphinine 2-Oxides

Synthesis and Cytostatic Activity of 4-bromo-5-ethyl-2-(ethylamino)- 5-methyl-5H-1,2-oxaphosphole 2-oxide

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