Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids
New quaternary 3-phthalimidopropylammonium conjugates of steroids were obtained by reaction of sterols (ergosterol, cholesterol, cholestanol) and bile acids (lithocholic, deoxycholic, cholic) with bromoacetic acid bromide to give sterol 3β-bromoacetates and bile acid 3α-bromoacetates, respectively....
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| Format: | Article |
| Language: | English |
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MDPI AG
2014-04-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/4/4212 |
| _version_ | 1818517890700148736 |
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| author | Bogumil Brycki Hanna Koenig Iwona Kowalczyk Tomasz Pospieszny |
| author_facet | Bogumil Brycki Hanna Koenig Iwona Kowalczyk Tomasz Pospieszny |
| author_sort | Bogumil Brycki |
| collection | DOAJ |
| description | New quaternary 3-phthalimidopropylammonium conjugates of steroids were obtained by reaction of sterols (ergosterol, cholesterol, cholestanol) and bile acids (lithocholic, deoxycholic, cholic) with bromoacetic acid bromide to give sterol 3β-bromoacetates and bile acid 3α-bromoacetates, respectively. These intermediates were subjected to nuclephilic substitution with N,N-dimethyl-3-phthalimidopropylamine to give the final quaternary ammonium salts. The structures of products were confirmed by spectral (1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry (ESI-MS, MALDI) as well as PM5 semiempirical methods and B3LYP ab initio methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS). |
| first_indexed | 2024-12-11T01:02:22Z |
| format | Article |
| id | doaj.art-39208d93362f49ce80993c8f4ca431c0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T01:02:22Z |
| publishDate | 2014-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-39208d93362f49ce80993c8f4ca431c02022-12-22T01:26:17ZengMDPI AGMolecules1420-30492014-04-011944212423310.3390/molecules19044212molecules19044212Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile AcidsBogumil Brycki0Hanna Koenig1Iwona Kowalczyk2Tomasz Pospieszny3Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandLaboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandLaboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandLaboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandNew quaternary 3-phthalimidopropylammonium conjugates of steroids were obtained by reaction of sterols (ergosterol, cholesterol, cholestanol) and bile acids (lithocholic, deoxycholic, cholic) with bromoacetic acid bromide to give sterol 3β-bromoacetates and bile acid 3α-bromoacetates, respectively. These intermediates were subjected to nuclephilic substitution with N,N-dimethyl-3-phthalimidopropylamine to give the final quaternary ammonium salts. The structures of products were confirmed by spectral (1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry (ESI-MS, MALDI) as well as PM5 semiempirical methods and B3LYP ab initio methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).http://www.mdpi.com/1420-3049/19/4/4212sterolsbile acidsquaternary ammonium saltconjugatesN,N-dimethyl-3-phthalimidopropylaminePASSPM5 calculationsB3LYP ab initio methods |
| spellingShingle | Bogumil Brycki Hanna Koenig Iwona Kowalczyk Tomasz Pospieszny Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids Molecules sterols bile acids quaternary ammonium salt conjugates N,N-dimethyl-3-phthalimidopropylamine PASS PM5 calculations B3LYP ab initio methods |
| title | Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids |
| title_full | Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids |
| title_fullStr | Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids |
| title_full_unstemmed | Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids |
| title_short | Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids |
| title_sort | synthesis spectroscopic and theoretical studies of new quaternary n n dimethyl 3 phthalimidopropylammonium conjugates of sterols and bile acids |
| topic | sterols bile acids quaternary ammonium salt conjugates N,N-dimethyl-3-phthalimidopropylamine PASS PM5 calculations B3LYP ab initio methods |
| url | http://www.mdpi.com/1420-3049/19/4/4212 |
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