Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities
The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a–2i, 4a–4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) wit...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI - Open Access Publishing
2017
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| Online Access: | http://umpir.ump.edu.my/id/eprint/19768/1/fist-2017-nadeem-Efficient%20Synthesis%20of%20Novel%20Pyridine-Based.pdf |
| _version_ | 1825811851037900800 |
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| author | Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen |
| author_facet | Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen |
| author_sort | Gulraiz, Ahmad |
| collection | UMP |
| description | The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a–2i, 4a–4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) with several arylboronic acids produced these novel pyridine derivatives in moderate to good yield. Density functional theory (DFT) studies were carried out for the pyridine derivatives 2a–2i and 4a–4i by using B3LYP/6-31G(d,p) basis with the help of GAUSSIAN 09 suite programme. The frontier molecular orbitals analysis, reactivity indices, molecular electrostatic potential and dipole measurements with the help of DFT methods, described the possible reaction pathways and potential candidates as chiral dopants for liquid crystals. The anti-thrombolytic, biofilm inhibition and haemolytic activities of pyridine derivatives were also investigated. In particular, the compound 4b exhibited the highest percentage lysis value (41.32%) against clot formation in human blood among all newly synthesized compounds. In addition, the compound 4f was found to be the most potent against Escherichia coli with an inhibition value of 91.95%. The rest of the pyridine derivatives displayed moderate biological activities. |
| first_indexed | 2024-03-06T12:20:28Z |
| format | Article |
| id | UMPir19768 |
| institution | Universiti Malaysia Pahang |
| language | English |
| last_indexed | 2024-03-06T12:20:28Z |
| publishDate | 2017 |
| publisher | MDPI - Open Access Publishing |
| record_format | dspace |
| spelling | UMPir197682017-12-29T05:23:12Z http://umpir.ump.edu.my/id/eprint/19768/ Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen Q Science (General) The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a–2i, 4a–4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) with several arylboronic acids produced these novel pyridine derivatives in moderate to good yield. Density functional theory (DFT) studies were carried out for the pyridine derivatives 2a–2i and 4a–4i by using B3LYP/6-31G(d,p) basis with the help of GAUSSIAN 09 suite programme. The frontier molecular orbitals analysis, reactivity indices, molecular electrostatic potential and dipole measurements with the help of DFT methods, described the possible reaction pathways and potential candidates as chiral dopants for liquid crystals. The anti-thrombolytic, biofilm inhibition and haemolytic activities of pyridine derivatives were also investigated. In particular, the compound 4b exhibited the highest percentage lysis value (41.32%) against clot formation in human blood among all newly synthesized compounds. In addition, the compound 4f was found to be the most potent against Escherichia coli with an inhibition value of 91.95%. The rest of the pyridine derivatives displayed moderate biological activities. MDPI - Open Access Publishing 2017 Article PeerReviewed application/pdf en cc_by http://umpir.ump.edu.my/id/eprint/19768/1/fist-2017-nadeem-Efficient%20Synthesis%20of%20Novel%20Pyridine-Based.pdf Gulraiz, Ahmad and Rasool, Nasir and Ikram, Hafiz Mansoor and Khan, Samreen Gul and Mahmood, Tariq and Ayub, Khurshid and Zubair, Muhammad and Al-Zahrani, Eman and Rana, Usman Ali and Akhtar, Muhammad Nadeem and Noorjahan Banu, Alitheen (2017) Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities. Molecules, 22 (2). pp. 1-19. ISSN 1420-3049 (print); 1420-3049 (online). (Published) http://dx.doi.org/10.3390/molecules22020190 doi: 10.3390/molecules22020190 |
| spellingShingle | Q Science (General) Gulraiz, Ahmad Rasool, Nasir Ikram, Hafiz Mansoor Khan, Samreen Gul Mahmood, Tariq Ayub, Khurshid Zubair, Muhammad Al-Zahrani, Eman Rana, Usman Ali Akhtar, Muhammad Nadeem Noorjahan Banu, Alitheen Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities |
| title | Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities |
| title_full | Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities |
| title_fullStr | Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities |
| title_full_unstemmed | Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities |
| title_short | Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities |
| title_sort | efficient synthesis of novel pyridine based derivatives via suzuki cross coupling reaction of commercially available 5 bromo 2 methylpyridin 3 amine quantum mechanical investigations and biological activities |
| topic | Q Science (General) |
| url | http://umpir.ump.edu.my/id/eprint/19768/1/fist-2017-nadeem-Efficient%20Synthesis%20of%20Novel%20Pyridine-Based.pdf |
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