Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues
Ferrocenyl amides (FB1-FB13) and their organic analogues (BZ1-BZ13) were prepared by a low-temperature condensation method. Ferrocenyl amides were synthesised using 4-ferrocenylbenzoyl chloride and ether-based amines and diamines. Benzoyl chloride was used to synthesise organic analogues by reacting...
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MDPI AG
2020-06-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/10/6/480 |
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| author | Sana Waseem Abbasi Naveed Zafar Ali Martin Etter Muhammad Shabbir Zareen Akhter Stacey J. Smith Hammad Ismail Bushra Mirza |
| author_facet | Sana Waseem Abbasi Naveed Zafar Ali Martin Etter Muhammad Shabbir Zareen Akhter Stacey J. Smith Hammad Ismail Bushra Mirza |
| author_sort | Sana Waseem Abbasi |
| collection | DOAJ |
| description | Ferrocenyl amides (FB1-FB13) and their organic analogues (BZ1-BZ13) were prepared by a low-temperature condensation method. Ferrocenyl amides were synthesised using 4-ferrocenylbenzoyl chloride and ether-based amines and diamines. Benzoyl chloride was used to synthesise organic analogues by reacting with various amines. The synthesised compounds were characterised by elemental, spectroscopic (FT-IR and NMR) and single crystal X-ray diffraction methods. Crystal structures of the representative organic analogues (BZ2 and BZ6) were solved by single crystal X-ray diffraction. BZ2 crystallises in the triclinic space group <i>P</i><inline-formula> <math display="inline"> <semantics> <mrow> <mover accent="true"> <mn>1</mn> <mo>¯</mo> </mover> </mrow> </semantics> </math> </inline-formula> with a unit cell volume of V = 1056.6(3) Å<sup>3</sup> and with two formula units per unit cell. Whereas BZ6 assembles in the orthorhombic space group <i>Pbca</i> with four formula units per unit cell and a unit cell volume of V = 1354.7(2) Å<sup>3</sup>. Spectral studies confirmed the presence of amide linkages in the synthesised compound with a strong N—H·····O=C hydrogen bonding network established between amide groups of neighbouring molecular scaffolds further stabilising the molecular stacking in accordance with the archetypal crystal structures. The bioactive nature of each compound was assessed by DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging activity, hydrogen peroxide scavenging activity and total antioxidant activity. Antidiabetic, anticholinesterase enzyme inhibition tests, as well as antibacterial activities, were performed showing significant biological activity for ferrocenyl amides as compared to their organic analogues. |
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| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T19:21:30Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
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| series | Crystals |
| spelling | doaj.art-11fd806d13c64905b8b590c4d39daeb62023-11-20T02:53:37ZengMDPI AGCrystals2073-43522020-06-0110648010.3390/cryst10060480Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic AnaloguesSana Waseem Abbasi0Naveed Zafar Ali1Martin Etter2Muhammad Shabbir3Zareen Akhter4Stacey J. Smith5Hammad Ismail6Bushra Mirza7Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanNational Centre for Physics, Quaid-i-Azam University, Islamabad 44000, PakistanDeutsches Elektronen-Synchrotron (DESY), 22607 Hamburg, GermanyDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry & Biochemistry, Brigham Young University, Provo, UT 84604, USADepartment of Biochemistry & Molecular Biology, University of Gujrat, Gujrat 50700, PakistanDepartment of Biochemistry, Quaid-i-Azam University, Islamabad 45320, PakistanFerrocenyl amides (FB1-FB13) and their organic analogues (BZ1-BZ13) were prepared by a low-temperature condensation method. Ferrocenyl amides were synthesised using 4-ferrocenylbenzoyl chloride and ether-based amines and diamines. Benzoyl chloride was used to synthesise organic analogues by reacting with various amines. The synthesised compounds were characterised by elemental, spectroscopic (FT-IR and NMR) and single crystal X-ray diffraction methods. Crystal structures of the representative organic analogues (BZ2 and BZ6) were solved by single crystal X-ray diffraction. BZ2 crystallises in the triclinic space group <i>P</i><inline-formula> <math display="inline"> <semantics> <mrow> <mover accent="true"> <mn>1</mn> <mo>¯</mo> </mover> </mrow> </semantics> </math> </inline-formula> with a unit cell volume of V = 1056.6(3) Å<sup>3</sup> and with two formula units per unit cell. Whereas BZ6 assembles in the orthorhombic space group <i>Pbca</i> with four formula units per unit cell and a unit cell volume of V = 1354.7(2) Å<sup>3</sup>. Spectral studies confirmed the presence of amide linkages in the synthesised compound with a strong N—H·····O=C hydrogen bonding network established between amide groups of neighbouring molecular scaffolds further stabilising the molecular stacking in accordance with the archetypal crystal structures. The bioactive nature of each compound was assessed by DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging activity, hydrogen peroxide scavenging activity and total antioxidant activity. Antidiabetic, anticholinesterase enzyme inhibition tests, as well as antibacterial activities, were performed showing significant biological activity for ferrocenyl amides as compared to their organic analogues.https://www.mdpi.com/2073-4352/10/6/480ferrocenyl amidesorganic amidesbiological activities |
| spellingShingle | Sana Waseem Abbasi Naveed Zafar Ali Martin Etter Muhammad Shabbir Zareen Akhter Stacey J. Smith Hammad Ismail Bushra Mirza Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues Crystals ferrocenyl amides organic amides biological activities |
| title | Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues |
| title_full | Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues |
| title_fullStr | Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues |
| title_full_unstemmed | Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues |
| title_short | Synthesis, Characterization and Biological Studies of Ether–Based Ferrocenyl Amides and their Organic Analogues |
| title_sort | synthesis characterization and biological studies of ether based ferrocenyl amides and their organic analogues |
| topic | ferrocenyl amides organic amides biological activities |
| url | https://www.mdpi.com/2073-4352/10/6/480 |
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