A Mechanistic Study on the Formation of Dronic Acids
Dronic acid derivatives, important drugs against bone diseases, may be synthesized from the corresponding substituted acetic acid either by reaction with phosphorus trichloride in methanesulfonic acid as the solvent or by using also phosphorous acid as the P-reactant if sulfolane is applied as the m...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2021-12, Vol.26 (24), p.7587 |
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| creator | Ábrányi-Balogh, Péter Greiner, István Keglevich, György |
| description | Dronic acid derivatives, important drugs against bone diseases, may be synthesized from the corresponding substituted acetic acid either by reaction with phosphorus trichloride in methanesulfonic acid as the solvent or by using also phosphorous acid as the P-reactant if sulfolane is applied as the medium. The energetics of the two protocols were evaluated by high-level quantum chemical calculations on the formation of fenidronic acid and benzidronic acid. The second option, involving (HO)
P-O-PCl
as the nucleophile, was found to be more favorable over the first variation, comprising Cl
P-O-SO
Me as the real reagent, especially for the case of benzidronate. |
| doi_str_mv | 10.3390/molecules26247587 |
| format | Article |
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P-O-PCl
as the nucleophile, was found to be more favorable over the first variation, comprising Cl
P-O-SO
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P-O-PCl
as the nucleophile, was found to be more favorable over the first variation, comprising Cl
P-O-SO
Me as the real reagent, especially for the case of benzidronate.</description><subject>Acetic acid</subject><subject>Acids</subject><subject>Bone diseases</subject><subject>carboxylic acid</subject><subject>Chloride</subject><subject>Chlorides</subject><subject>dronic acid</subject><subject>Energy</subject><subject>mechanism</subject><subject>Methanesulfonic acid</subject><subject>Phosphorous acid</subject><subject>Phosphorus</subject><subject>phosphorus trichloride</subject><subject>Reagents</subject><subject>Solvents</subject><subject>Sulfolane</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>DOA</sourceid><recordid>eNplkclOwzAQhi0EgrI8ABcUiQuXgrd4uSBVhQJSEQe4W7bjtKmSuNgJUt8elwJqwQev_3wz_geAcwSvCZHwpvG1s33tImaY8lzwPTBAFMMhgVTub-2PwHGMCwgxoig_BEeESsoYkwNAR9mzs3PdVrGrbPba9cUq823WzV028aHRXZVOvszugm-TYGSrIp6Cg1LX0Z19ryfgbXL_Nn4cTl8ensaj6dBSSbqh4ZgyiRlJaWWpGSewEAXT1ApkSmdkYZ3NpeRWYoQpMZRyZ5gphIQQcXICnjbYwuuFWoaq0WGlvK7U14UPM6VDqrp2yhisMccGFkhTCY2AOcupcXma0kCJdbthLXvTuJS47YKud6C7L201VzP_oQSHIpmbAFffgODfexc71VTRurrWrfN9VJgltwniYp3r8o904fvQJqfWKiwwRGwNRBuVDT7G4MrfYhBU6_aqf-1NMRfbv_iN-Okn-QSCraEN</recordid><startdate>20211214</startdate><enddate>20211214</enddate><creator>Ábrányi-Balogh, Péter</creator><creator>Greiner, István</creator><creator>Keglevich, György</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-9284-5160</orcidid><orcidid>https://orcid.org/0000-0002-5336-2828</orcidid><orcidid>https://orcid.org/0000-0002-5366-472X</orcidid></search><sort><creationdate>20211214</creationdate><title>A Mechanistic Study on the Formation of Dronic Acids</title><author>Ábrányi-Balogh, Péter ; 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The energetics of the two protocols were evaluated by high-level quantum chemical calculations on the formation of fenidronic acid and benzidronic acid. The second option, involving (HO)
P-O-PCl
as the nucleophile, was found to be more favorable over the first variation, comprising Cl
P-O-SO
Me as the real reagent, especially for the case of benzidronate.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>34946669</pmid><doi>10.3390/molecules26247587</doi><orcidid>https://orcid.org/0000-0002-9284-5160</orcidid><orcidid>https://orcid.org/0000-0002-5336-2828</orcidid><orcidid>https://orcid.org/0000-0002-5366-472X</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acetic acid Acids Bone diseases carboxylic acid Chloride Chlorides dronic acid Energy mechanism Methanesulfonic acid Phosphorous acid Phosphorus phosphorus trichloride Reagents Solvents Sulfolane |
| title | A Mechanistic Study on the Formation of Dronic Acids |
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