Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes
Herein, a new series of azo ligands HL-1 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-2 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxy-2-thioxottetrahydropyrimidin-4one), HL-3 (5-(2,4-dichloro-6-(phenylcarbonyl)phenyl) diazenyl)-6-hydroxydihydr...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-01-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S240584402203780X |
| _version_ | 1811173392466837504 |
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| author | Tariq Aziz Hafiza Ammara Nasim Khalil Ahmad Habib-ur-Rehman Shah Sajidah Parveen Muhammad Mahboob Ahmad Hammad Majeed Ahmad M. Galal Abdul Rauf Muhammad Ashfaq |
| author_facet | Tariq Aziz Hafiza Ammara Nasim Khalil Ahmad Habib-ur-Rehman Shah Sajidah Parveen Muhammad Mahboob Ahmad Hammad Majeed Ahmad M. Galal Abdul Rauf Muhammad Ashfaq |
| author_sort | Tariq Aziz |
| collection | DOAJ |
| description | Herein, a new series of azo ligands HL-1 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-2 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxy-2-thioxottetrahydropyrimidin-4one), HL-3 (5-(2,4-dichloro-6-(phenylcarbonyl)phenyl) diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-4 (5-(2,4-dichloro-6-(phenylcarbonyl) phenyl)diazenyl)-6-hydroxy-2-thioxotetrahydropyrimidin-4one) and their metal complexes with Cu(II) & Ni(II) were synthesized successfully having excellent yield, in reproducible conditions and for structure elucidation different advance spectroscopic techniques (FTIR, 1H NMR, 13C NMR and Mass Spectrometry) were applied. In FTIR analysis, the absence of peak at 3450-3550 cm-1 due to –NH2 and presence of a new peak of N=N at 1390-1520 cm−1 confirmed synthesis of the ligands. The 1H NMR spectra of azo ligands showed singlet peak at 11.5–13.5 ppm (Ar-OH) for hydroxyl group and –NH2 signals disappearance of anilines at 4–5 ppm also gives strong indication for the synthesis of azo compounds. On complexation two most important peaks (M-O, M-N) appeared in all the metal chelates in the range of 400–600 cm−1 which were not present in any of the ligands, confirmed the formation of complexes. Molecular ion peaks in mass spectra at 273, 388, 407 and 423 m/z value for ligands as well as for complexes at 803, 835, 871 and 904 m/z also give strong indication that proposed ligands and their metal complexes are produced successfully. Biological screening of the synthesized compounds were also carried out against different bacterial strains (E.coli, S.typhi, and B.subtilis), antifungal (C.albicans, A.niger, and C.glabrata) strains and antioxidant activity. From results it was observed that HL-4 and Cu complexes exhibited maximum inhibition against all bacterial and fungal strains as compared to other ligands and standard drug. |
| first_indexed | 2024-04-10T17:46:05Z |
| format | Article |
| id | doaj.art-1394fb904d8a464f9b0e807467f9f55d |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-10T17:46:05Z |
| publishDate | 2023-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-1394fb904d8a464f9b0e807467f9f55d2023-02-03T04:58:23ZengElsevierHeliyon2405-84402023-01-0191e12492Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexesTariq Aziz0Hafiza Ammara Nasim1Khalil Ahmad2Habib-ur-Rehman Shah3Sajidah Parveen4Muhammad Mahboob Ahmad5Hammad Majeed6Ahmad M. Galal7Abdul Rauf8Muhammad Ashfaq9Institute of Chemistry, Baghdad ul Jadeed Campus, The Islamia University of Bahawalpur, Bahawalpur, 63100, PakistanInstitute of Chemistry, Baghdad ul Jadeed Campus, The Islamia University of Bahawalpur, Bahawalpur, 63100, PakistanUniversity of Management and Technology (UMT) Sialkot Campus, Sialkot, Punjab, Pakistan; Cholistan University of Veterinary and Animal Sciences (CUVAS), Bahawalpur, Punjab, Pakistan; Corresponding author.Institute of Chemistry, Baghdad ul Jadeed Campus, The Islamia University of Bahawalpur, Bahawalpur, 63100, PakistanInstitute of Chemistry, Baghdad ul Jadeed Campus, The Islamia University of Bahawalpur, Bahawalpur, 63100, PakistanInstitute of Chemical Sciences, Bahauddin Zakariya University Multan, PakistanUniversity of Management and Technology (UMT) Sialkot Campus, Sialkot, Punjab, PakistanDepartment of Mechanical Engineering, College of Engineering in Wadi Alddawasir, Prince Sattam Bin Abdul-Aziz University, Al-Kharj, 16278, Saudi Arabia; Production Engineering and Mechanical Design Department, Faculty of Engineering, Mansoura University, Mansoura P.O. 35516, EgyptInstitute of Chemistry, Baghdad ul Jadeed Campus, The Islamia University of Bahawalpur, Bahawalpur, 63100, PakistanInstitute of Chemistry, Baghdad ul Jadeed Campus, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan; Corresponding author.Herein, a new series of azo ligands HL-1 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-2 (5-(2-chloro-6-(phenylcarbonyl)phenyl)diazenyl)-6-hydroxy-2-thioxottetrahydropyrimidin-4one), HL-3 (5-(2,4-dichloro-6-(phenylcarbonyl)phenyl) diazenyl)-6-hydroxydihydropyrimidines-2,4dione), HL-4 (5-(2,4-dichloro-6-(phenylcarbonyl) phenyl)diazenyl)-6-hydroxy-2-thioxotetrahydropyrimidin-4one) and their metal complexes with Cu(II) & Ni(II) were synthesized successfully having excellent yield, in reproducible conditions and for structure elucidation different advance spectroscopic techniques (FTIR, 1H NMR, 13C NMR and Mass Spectrometry) were applied. In FTIR analysis, the absence of peak at 3450-3550 cm-1 due to –NH2 and presence of a new peak of N=N at 1390-1520 cm−1 confirmed synthesis of the ligands. The 1H NMR spectra of azo ligands showed singlet peak at 11.5–13.5 ppm (Ar-OH) for hydroxyl group and –NH2 signals disappearance of anilines at 4–5 ppm also gives strong indication for the synthesis of azo compounds. On complexation two most important peaks (M-O, M-N) appeared in all the metal chelates in the range of 400–600 cm−1 which were not present in any of the ligands, confirmed the formation of complexes. Molecular ion peaks in mass spectra at 273, 388, 407 and 423 m/z value for ligands as well as for complexes at 803, 835, 871 and 904 m/z also give strong indication that proposed ligands and their metal complexes are produced successfully. Biological screening of the synthesized compounds were also carried out against different bacterial strains (E.coli, S.typhi, and B.subtilis), antifungal (C.albicans, A.niger, and C.glabrata) strains and antioxidant activity. From results it was observed that HL-4 and Cu complexes exhibited maximum inhibition against all bacterial and fungal strains as compared to other ligands and standard drug.http://www.sciencedirect.com/science/article/pii/S240584402203780XAzo compoundsAntimicrobial agentsAntioxidantMetal complexes |
| spellingShingle | Tariq Aziz Hafiza Ammara Nasim Khalil Ahmad Habib-ur-Rehman Shah Sajidah Parveen Muhammad Mahboob Ahmad Hammad Majeed Ahmad M. Galal Abdul Rauf Muhammad Ashfaq Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes Heliyon Azo compounds Antimicrobial agents Antioxidant Metal complexes |
| title | Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes |
| title_full | Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes |
| title_fullStr | Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes |
| title_full_unstemmed | Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes |
| title_short | Rational synthesis, biological screening of azo derivatives of chloro-phenylcarbonyl diazenyl hydroxy dipyrimidines/thioxotetrahydropyrimidines and their metal complexes |
| title_sort | rational synthesis biological screening of azo derivatives of chloro phenylcarbonyl diazenyl hydroxy dipyrimidines thioxotetrahydropyrimidines and their metal complexes |
| topic | Azo compounds Antimicrobial agents Antioxidant Metal complexes |
| url | http://www.sciencedirect.com/science/article/pii/S240584402203780X |
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