Synthesis and in vitro cytotoxicity evaluation of some N-substituted α-amino acid derivatives containing a hexahydropyrimidine moiety
This work reports a one-pot synthesis of diastereomerically pure N -substituted derivatives of natural amino acids containing a hexahydropyrimidine moiety in 71–89% yields by Mannich reaction of ethyl acetoacetate or 3-oxobutanamide with formaldehyde and amino acid hydrochlorides in acetate buffer (...
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| Veröffentlicht in: | Medicinal chemistry research 2017-05, Vol.26 (5), p.900-908 |
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| container_title | Medicinal chemistry research |
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| creator | Latypova, Dilara R. Badamshin, Alexander G. Gibadullina, Natalya N. Khusnutdinova, Nailya S. Zainullina, Liana F. Vakhitova, Yulia V. Tomilov, Yury V. Dokichev, Vladimir A. |
| description | This work reports a one-pot synthesis of diastereomerically pure
N
-substituted derivatives of natural amino acids containing a hexahydropyrimidine moiety in 71–89% yields by Mannich reaction of ethyl acetoacetate or 3-oxobutanamide with formaldehyde and amino acid hydrochlorides in acetate buffer (AcONa–AcOH, pH 4) at room temperature. The in vitro cytotoxic activities of the compounds obtained were determined in cancer (Jurkat and SH-SY5Y) and conditionally normal (HEK293) human cells. |
| doi_str_mv | 10.1007/s00044-017-1802-4 |
| format | Article |
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N
-substituted derivatives of natural amino acids containing a hexahydropyrimidine moiety in 71–89% yields by Mannich reaction of ethyl acetoacetate or 3-oxobutanamide with formaldehyde and amino acid hydrochlorides in acetate buffer (AcONa–AcOH, pH 4) at room temperature. The in vitro cytotoxic activities of the compounds obtained were determined in cancer (Jurkat and SH-SY5Y) and conditionally normal (HEK293) human cells.</description><subject>Acetic acid</subject><subject>Amino acids</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Cell Biology</subject><subject>Chemical synthesis</subject><subject>Cytotoxicity</subject><subject>Hydrochlorides</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Room temperature</subject><subject>Substitutes</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kEFOLCEQhjtGE33qAdyRuEYLGprupTHqe4nRhbomCNUOxoER6Il9Ae_jRTyTmHHxNq6qFt__V-VrmiMGJwxAnWYAEIICU5T1wKnYavaYlIL2jMN23aHuXPJ2t_mT8zNAq0DIveb9bg5lgdlnYoIjPpC1LykSO5dY4pu3vswE1-ZlMsXHQOJIclwiuaF5eszFl6mgI58f1Cx9iMRY74jD5NcVX2MmNoZifPDhiRiywDezmF2Kqzn5pXc-IFlGj2U-aHZG85Lx8GfuNw-XF_fnf-n17dW_87NralvWFWoe3ei4RNW7Dh0bWtGPrZBWKjeojknXqWFUUra95dhxGLgbmBLcAhrOHLb7zfGmd5Xi64S56Oc4pVBPatb3QkrgLasU21A2xZwTjnpV_zVp1gz0t2690a2rbv2tW4ua4ZtMrmx4wvRf86-hL9fwhk0</recordid><startdate>20170501</startdate><enddate>20170501</enddate><creator>Latypova, Dilara R.</creator><creator>Badamshin, Alexander G.</creator><creator>Gibadullina, Natalya N.</creator><creator>Khusnutdinova, Nailya S.</creator><creator>Zainullina, Liana F.</creator><creator>Vakhitova, Yulia V.</creator><creator>Tomilov, Yury V.</creator><creator>Dokichev, Vladimir A.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope></search><sort><creationdate>20170501</creationdate><title>Synthesis and in vitro cytotoxicity evaluation of some N-substituted α-amino acid derivatives containing a hexahydropyrimidine moiety</title><author>Latypova, Dilara R. ; Badamshin, Alexander G. ; Gibadullina, Natalya N. ; Khusnutdinova, Nailya S. ; Zainullina, Liana F. ; Vakhitova, Yulia V. ; Tomilov, Yury V. ; Dokichev, Vladimir A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-abdfd25e78d6ed19348f345c57d97615d679f75538c2e62092d91742c0ea21de3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acetic acid</topic><topic>Amino acids</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Cell Biology</topic><topic>Chemical synthesis</topic><topic>Cytotoxicity</topic><topic>Hydrochlorides</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Room temperature</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Latypova, Dilara R.</creatorcontrib><creatorcontrib>Badamshin, Alexander G.</creatorcontrib><creatorcontrib>Gibadullina, Natalya N.</creatorcontrib><creatorcontrib>Khusnutdinova, Nailya S.</creatorcontrib><creatorcontrib>Zainullina, Liana F.</creatorcontrib><creatorcontrib>Vakhitova, Yulia V.</creatorcontrib><creatorcontrib>Tomilov, Yury V.</creatorcontrib><creatorcontrib>Dokichev, Vladimir A.</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Latypova, Dilara R.</au><au>Badamshin, Alexander G.</au><au>Gibadullina, Natalya N.</au><au>Khusnutdinova, Nailya S.</au><au>Zainullina, Liana F.</au><au>Vakhitova, Yulia V.</au><au>Tomilov, Yury V.</au><au>Dokichev, Vladimir A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and in vitro cytotoxicity evaluation of some N-substituted α-amino acid derivatives containing a hexahydropyrimidine moiety</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2017-05-01</date><risdate>2017</risdate><volume>26</volume><issue>5</issue><spage>900</spage><epage>908</epage><pages>900-908</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>This work reports a one-pot synthesis of diastereomerically pure
N
-substituted derivatives of natural amino acids containing a hexahydropyrimidine moiety in 71–89% yields by Mannich reaction of ethyl acetoacetate or 3-oxobutanamide with formaldehyde and amino acid hydrochlorides in acetate buffer (AcONa–AcOH, pH 4) at room temperature. The in vitro cytotoxic activities of the compounds obtained were determined in cancer (Jurkat and SH-SY5Y) and conditionally normal (HEK293) human cells.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s00044-017-1802-4</doi><tpages>9</tpages></addata></record> |
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| subjects | Acetic acid Amino acids Biochemistry Biomedical and Life Sciences Biomedicine Cell Biology Chemical synthesis Cytotoxicity Hydrochlorides Original Research Pharmacology/Toxicology Room temperature Substitutes |
| title | Synthesis and in vitro cytotoxicity evaluation of some N-substituted α-amino acid derivatives containing a hexahydropyrimidine moiety |
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