Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity
Nicotinoyl- and isonicotinoylhydrazones of 2-dimethoxyphosphoryl-2-methylpentan-4-one (the active ingredient of the medicinal preparation Dimephosphone) were synthesized. It was shown that crystals of both hydrazones contained a single spatial form of the E C=N isomer. The dimephosphone pyridinoylhy...
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| Veröffentlicht in: | Pharmaceutical chemistry journal 2013-04, Vol.47 (1), p.35-39 |
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| container_title | Pharmaceutical chemistry journal |
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| creator | Buzykin, B. I. Nabiullin, V. N. Garaev, R. S. Chestnova, R. V. Kashapov, L. R. Valeev, R. Sh Mironov, V. F. |
| description | Nicotinoyl- and isonicotinoylhydrazones of 2-dimethoxyphosphoryl-2-methylpentan-4-one (the active ingredient of the medicinal preparation Dimephosphone) were synthesized. It was shown that crystals of both hydrazones contained a single spatial form of the E
C=N
isomer. The dimephosphone pyridinoylhydrazones existed in slightly polar and polar solvents as a mixture of two amide conformers of a single E
C=N
isomer. This was due to hindered rotation of the molecular fragments around the (O=)C–N amide bond. The ratio of conformers was determined by the solvent and the time of solution preparation. Both hydrazones possessed low toxicity and high antimycobacterial activity. |
| doi_str_mv | 10.1007/s11094-013-0891-8 |
| format | Article |
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C=N
isomer. The dimephosphone pyridinoylhydrazones existed in slightly polar and polar solvents as a mixture of two amide conformers of a single E
C=N
isomer. This was due to hindered rotation of the molecular fragments around the (O=)C–N amide bond. The ratio of conformers was determined by the solvent and the time of solution preparation. Both hydrazones possessed low toxicity and high antimycobacterial activity.</description><identifier>ISSN: 0091-150X</identifier><identifier>EISSN: 1573-9031</identifier><identifier>DOI: 10.1007/s11094-013-0891-8</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Antitubercular agents ; Medicine ; Nuclear magnetic resonance spectroscopy ; Organic Chemistry ; Pharmacology/Toxicology ; Pharmacy</subject><ispartof>Pharmaceutical chemistry journal, 2013-04, Vol.47 (1), p.35-39</ispartof><rights>Springer Science+Business Media New York 2013</rights><rights>COPYRIGHT 2013 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c355t-e7e107888c8928b3599efd87b6c8c5f17187a3a3281e0b673c049c771eed1db33</citedby><cites>FETCH-LOGICAL-c355t-e7e107888c8928b3599efd87b6c8c5f17187a3a3281e0b673c049c771eed1db33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11094-013-0891-8$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11094-013-0891-8$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Buzykin, B. I.</creatorcontrib><creatorcontrib>Nabiullin, V. N.</creatorcontrib><creatorcontrib>Garaev, R. S.</creatorcontrib><creatorcontrib>Chestnova, R. V.</creatorcontrib><creatorcontrib>Kashapov, L. R.</creatorcontrib><creatorcontrib>Valeev, R. Sh</creatorcontrib><creatorcontrib>Mironov, V. F.</creatorcontrib><title>Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity</title><title>Pharmaceutical chemistry journal</title><addtitle>Pharm Chem J</addtitle><description>Nicotinoyl- and isonicotinoylhydrazones of 2-dimethoxyphosphoryl-2-methylpentan-4-one (the active ingredient of the medicinal preparation Dimephosphone) were synthesized. It was shown that crystals of both hydrazones contained a single spatial form of the E
C=N
isomer. The dimephosphone pyridinoylhydrazones existed in slightly polar and polar solvents as a mixture of two amide conformers of a single E
C=N
isomer. This was due to hindered rotation of the molecular fragments around the (O=)C–N amide bond. The ratio of conformers was determined by the solvent and the time of solution preparation. Both hydrazones possessed low toxicity and high antimycobacterial activity.</description><subject>Antitubercular agents</subject><subject>Medicine</subject><subject>Nuclear magnetic resonance spectroscopy</subject><subject>Organic Chemistry</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><issn>0091-150X</issn><issn>1573-9031</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kF9LwzAUxYMoOKcfwLeAz525Tbukj2P-hYHCFHyRkKbpmtGmI8mU-unNqC-CyOVy4XB-F85B6BLIDAhh1x6AFFlCgCaEF5DwIzSBnNGkIBSO0YSQKEJO3k7RmfdbQiJF0wl6Xw82NNobj6Wt8Dq4vQp7p3Ff4xvT6V3T-7hW4-fBmcrYfmiboXLyK2oef5rQ4IUNphtUX0oVtDOyxQsVzIcJwzk6qWXr9cXPnaLXu9uX5UOyerp_XC5WiaJ5HhLNNBDGOVe8SHlJ86LQdcVZOVdc5TUw4ExSSVMOmpRzRhXJCsUYaF1BVVI6RVfj341stTC27oOTqjNeiQWlc55laVpE1-wPV5xKd0bFPLWJ-i8ARkC53nuna7FzppNuEEDEoXYx1i5i7eJQu-CRSUfGR6_daCe2_d7ZmP4f6BskV4Yk</recordid><startdate>20130401</startdate><enddate>20130401</enddate><creator>Buzykin, B. I.</creator><creator>Nabiullin, V. N.</creator><creator>Garaev, R. S.</creator><creator>Chestnova, R. V.</creator><creator>Kashapov, L. R.</creator><creator>Valeev, R. Sh</creator><creator>Mironov, V. F.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130401</creationdate><title>Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity</title><author>Buzykin, B. I. ; Nabiullin, V. N. ; Garaev, R. S. ; Chestnova, R. V. ; Kashapov, L. R. ; Valeev, R. Sh ; Mironov, V. F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-e7e107888c8928b3599efd87b6c8c5f17187a3a3281e0b673c049c771eed1db33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Antitubercular agents</topic><topic>Medicine</topic><topic>Nuclear magnetic resonance spectroscopy</topic><topic>Organic Chemistry</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Buzykin, B. I.</creatorcontrib><creatorcontrib>Nabiullin, V. N.</creatorcontrib><creatorcontrib>Garaev, R. S.</creatorcontrib><creatorcontrib>Chestnova, R. V.</creatorcontrib><creatorcontrib>Kashapov, L. R.</creatorcontrib><creatorcontrib>Valeev, R. Sh</creatorcontrib><creatorcontrib>Mironov, V. F.</creatorcontrib><collection>CrossRef</collection><jtitle>Pharmaceutical chemistry journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Buzykin, B. I.</au><au>Nabiullin, V. N.</au><au>Garaev, R. S.</au><au>Chestnova, R. V.</au><au>Kashapov, L. R.</au><au>Valeev, R. Sh</au><au>Mironov, V. F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity</atitle><jtitle>Pharmaceutical chemistry journal</jtitle><stitle>Pharm Chem J</stitle><date>2013-04-01</date><risdate>2013</risdate><volume>47</volume><issue>1</issue><spage>35</spage><epage>39</epage><pages>35-39</pages><issn>0091-150X</issn><eissn>1573-9031</eissn><abstract>Nicotinoyl- and isonicotinoylhydrazones of 2-dimethoxyphosphoryl-2-methylpentan-4-one (the active ingredient of the medicinal preparation Dimephosphone) were synthesized. It was shown that crystals of both hydrazones contained a single spatial form of the E
C=N
isomer. The dimephosphone pyridinoylhydrazones existed in slightly polar and polar solvents as a mixture of two amide conformers of a single E
C=N
isomer. This was due to hindered rotation of the molecular fragments around the (O=)C–N amide bond. The ratio of conformers was determined by the solvent and the time of solution preparation. Both hydrazones possessed low toxicity and high antimycobacterial activity.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s11094-013-0891-8</doi><tpages>5</tpages></addata></record> |
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| subjects | Antitubercular agents Medicine Nuclear magnetic resonance spectroscopy Organic Chemistry Pharmacology/Toxicology Pharmacy |
| title | Synthesis and Structure of Dimephosphone Pyridinoylhydrazones with Antimycobacterial Activity |
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