Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents
A convenient one-pot, three-component synthesis of 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives (3a–k) by Chichibabin reaction has been reported. These compounds were synthesized by the reaction of 3-acetyl coumarin (1a) or 5-bromo 3-acetyl coumarin (1b) with substituted...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2017-02-01
|
| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535213000890 |
| _version_ | 1811213872609099776 |
|---|---|
| author | R. Kenchappa Yadav D. Bodke A. Chandrashekar Sandeep Telkar K.S. Manjunatha M. Aruna Sindhe |
| author_facet | R. Kenchappa Yadav D. Bodke A. Chandrashekar Sandeep Telkar K.S. Manjunatha M. Aruna Sindhe |
| author_sort | R. Kenchappa |
| collection | DOAJ |
| description | A convenient one-pot, three-component synthesis of 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives (3a–k) by Chichibabin reaction has been reported. These compounds were synthesized by the reaction of 3-acetyl coumarin (1a) or 5-bromo 3-acetyl coumarin (1b) with substituted aromatic aldehydes (2a–k) and ammonium acetate under acidic conditions and the structure was confirmed by FT-IR, 1H NMR, 13C NMR and Mass spectroscopic methods. The newly synthesized compounds (3a–k) were evaluated for antimicrobial activity, DPPH free radical scavenging activity and ferrous ion-chelating ability. The mode of action of these active compounds was carried out by docking receptor GlcN6P synthase. Compounds 3a, 3b, 3c, and 3d have displayed potential antimicrobial activity and some of the compounds have shown promising antioxidant properties. |
| first_indexed | 2024-04-12T05:53:35Z |
| format | Article |
| id | doaj.art-12cafd26298f49399b94a449dd1f2560 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-12T05:53:35Z |
| publishDate | 2017-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-12cafd26298f49399b94a449dd1f25602022-12-22T03:45:12ZengElsevierArabian Journal of Chemistry1878-53522017-02-0110S1S1336S134410.1016/j.arabjc.2013.03.020Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agentsR. Kenchappa0Yadav D. Bodke1A. Chandrashekar2Sandeep Telkar3K.S. Manjunatha4M. Aruna Sindhe5Department of P.G. Studies and Research in Industrial Chemistry, School of Chemical Science, JnanaSahyadri, Kuvempu University, Shankaraghatta, 577 451 Shivamogga, Karnataka, IndiaDepartment of P.G. Studies and Research in Industrial Chemistry, School of Chemical Science, JnanaSahyadri, Kuvempu University, Shankaraghatta, 577 451 Shivamogga, Karnataka, IndiaDepartment of P.G. Studies and Research in Industrial Chemistry, School of Chemical Science, JnanaSahyadri, Kuvempu University, Shankaraghatta, 577 451 Shivamogga, Karnataka, IndiaDepartment of P.G. Studies and Research in Biotechnology and Bioinformatics, Jnanasahyadri, Kuvempu University, Shankaraghatta 577 451, Karnataka, IndiaDepartment of P.G. Studies and Research in Pharmaceutical Chemistry, Kuvempu University, P.G. Centre, Kadur, 577 548 Chikkamagaluru Dt., Karnataka, IndiaDepartment of P.G. Studies and Research in Industrial Chemistry, School of Chemical Science, JnanaSahyadri, Kuvempu University, Shankaraghatta, 577 451 Shivamogga, Karnataka, IndiaA convenient one-pot, three-component synthesis of 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives (3a–k) by Chichibabin reaction has been reported. These compounds were synthesized by the reaction of 3-acetyl coumarin (1a) or 5-bromo 3-acetyl coumarin (1b) with substituted aromatic aldehydes (2a–k) and ammonium acetate under acidic conditions and the structure was confirmed by FT-IR, 1H NMR, 13C NMR and Mass spectroscopic methods. The newly synthesized compounds (3a–k) were evaluated for antimicrobial activity, DPPH free radical scavenging activity and ferrous ion-chelating ability. The mode of action of these active compounds was carried out by docking receptor GlcN6P synthase. Compounds 3a, 3b, 3c, and 3d have displayed potential antimicrobial activity and some of the compounds have shown promising antioxidant properties.http://www.sciencedirect.com/science/article/pii/S1878535213000890CoumarinDicoumarinyl pyridinesChichibabinAntimicrobialGlucosamine-6-phosphate synthaseAntioxidant |
| spellingShingle | R. Kenchappa Yadav D. Bodke A. Chandrashekar Sandeep Telkar K.S. Manjunatha M. Aruna Sindhe Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents Arabian Journal of Chemistry Coumarin Dicoumarinyl pyridines Chichibabin Antimicrobial Glucosamine-6-phosphate synthase Antioxidant |
| title | Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents |
| title_full | Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents |
| title_fullStr | Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents |
| title_full_unstemmed | Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents |
| title_short | Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents |
| title_sort | synthesis of some 2 6 bis 1 coumarin 2 yl 4 4 substituted phenyl pyridine derivatives as potent biological agents |
| topic | Coumarin Dicoumarinyl pyridines Chichibabin Antimicrobial Glucosamine-6-phosphate synthase Antioxidant |
| url | http://www.sciencedirect.com/science/article/pii/S1878535213000890 |
| work_keys_str_mv | AT rkenchappa synthesisofsome26bis1coumarin2yl44substitutedphenylpyridinederivativesaspotentbiologicalagents AT yadavdbodke synthesisofsome26bis1coumarin2yl44substitutedphenylpyridinederivativesaspotentbiologicalagents AT achandrashekar synthesisofsome26bis1coumarin2yl44substitutedphenylpyridinederivativesaspotentbiologicalagents AT sandeeptelkar synthesisofsome26bis1coumarin2yl44substitutedphenylpyridinederivativesaspotentbiologicalagents AT ksmanjunatha synthesisofsome26bis1coumarin2yl44substitutedphenylpyridinederivativesaspotentbiologicalagents AT marunasindhe synthesisofsome26bis1coumarin2yl44substitutedphenylpyridinederivativesaspotentbiologicalagents |