In this study, several aromatic groups were inserted to synthesize various4-oxo-1,4-dihydroquinazolin [4a-f] and 4-oxo-2H-benzo[1,3]thiazin[5a-f] linked to benzoimidazole rings. The chemical structures of the synthesized benzoimidazole derivatives were corroborated by physicochemical properties, elemental micro analysis (C,H,N) and some spectroscopic techniques such as (FTIR, 1H-NMR, 13C-NMR). In vitro antimicrobial assessmentfor newly synthesized target compounds against six types of pathogenic bacteria and one type of fungi was investigated which is comparable to azithromycin (as antibacterial), Itraconazole (antifungal) reference drugs.The results obtained showed that most of the compounds have a potential good to medium activity against these different types of microorganisms.
Cite this article:
Ayad Kareem Khan. Synthesis, Characterization and In vitro Antimicrobial Assessments of a New Series Benzoimidazoles Incorporated Quinazoline and Thiazine Analogues. Research Journal of Pharmacy and Technology. 2023; 16(8):3852-8. doi: 10.52711/0974-360X.2023.00636
Ayad Kareem Khan. Synthesis, Characterization and In vitro Antimicrobial Assessments of a New Series Benzoimidazoles Incorporated Quinazoline and Thiazine Analogues. Research Journal of Pharmacy and Technology. 2023; 16(8):3852-8. doi: 10.52711/0974-360X.2023.00636 Available on: https://rjptonline.org/AbstractView.aspx?PID=2023-16-8-56
1. M. Kavya M. Priya D. Green Chemistry approach for the synthesis of some Benzimidazole derivatives and their Biological Evaluation. Research J. Pharm. and Tech. 2019; 12(3): 1023-1030. doi: 10.5958/0974-360X.2019.00169.0
2. 2. Khalifa M. Gobouri A. Kabli F. Altalhi T. Almalki A. Mohamed M. Synthesis, antibacterial, and anti HepG2 cell line human hepatocyte carcinoma activity of some new potentially benzimidazole-5 (aryldiazenyl)thiazole derivatives. Molecules. 2018; 23(12): 1-16.
3. Vijey A. Anbhule S. Molecular Docking Q-SAR Studies of Benzimidazole as Antifungal Nucleus. Research J. Pharm. and Tech. 2021; 14(4):2191-2194. doi: 10.52711/0974-360X.2021.00388
4. Chikkula K. Sundararajan R. Analgesic, anti-inflammatory, and antimicrobial activities of novel isoxazole/pyrimidine/pyrazole substituted benzimidazole analogs. Med. Chem. Res. 2017; 26, 3026–3037.
5. Noor A. Qazi N. Nadeem H. Synthesis, characterization, anti-ulcer action and molecular docking evaluation of novel benzimidazole-pyrazole hybrids. Chem. Cent. J. 2017; 11, 85.
6. Rosalba F. Simone C. Serena V. Davide B. Teresa D. Screening of benzimidazole-based anthelmintics and their enantiomers as repurposed drug candidates in cancer therapy. Pharmaceuticals. 2021; 14(372): 1-16.
7. Prafulla Sabale, Dhiraj Bhagwat, Vidya Sabale. Synthesis and Anti-Tubercular Activity of Substituted Phenylpyrazole having Benzimidazole Ring. Research J. Pharm. and Tech. 2018; 11(8): 3599-3608. doi: 10.5958/0974-360X.2018.00662.5
8. Geetha S. Vijayakumar K. Synthesis, Characterization and the anti HIV1 behavior of some Novel Clubbed Benzimidazole derivatives approaches. Research J. Pharm. and Tech. 2020; 13(7): 3383-3388. doi: 10.5958/0974-360X.2020.00601.0
9. Veerasamy R. Roy A. Karunakaran R. Rajak H. Structure–activity relationship analysis of benzimidazoles as emerging anti-inflammatory agents: an overview. Pharmaceuticals. 2021; 14, 663.
10. Deepak K. Mrunal S. Synthesis and Evaluation of Antimicrobial, Antitubercular and Anticancer activities of Dihydrobenzimidazole thiopyranooxazinone derivatives. Research J. Pharm. and Tech. 2021; 14(3):1453-1458. doi: 10.5958/0974-360X.2021.00259.6
11. Vatsal M. Navin B. Manuel J. Gildardo R.N-Mannich bases of benzimidazole as a potent antitubercular and antiprotozoal agents: Their synthesis and computational studies. Synthetic Communications. 2020; 50 (6):858-878.
12. Umesh K. Rakesh N. Surendra K. Sachin K. Vivek G. Benzimidazole: Structure Activity Relationship and Mechanism of Action as Antimicrobial Agent. Research J. Pharm. and Tech. 2017; 10(7): 2400-2414. doi: 10.5958/0974-360X.2017.00425.5
13. Dik B. Coskun D. Bahcivan E. Uney K. Potential antidiabetic activity of benzimidazole derivative albendazole and lansoprazole drugs in different doses in experimental type 2 diabetic rats. Turk. J. Med. Sci. 2021; 51(3):1579-1586.
14. Hatem A. Rabab E. Mohamed M. El-Hassane A. Yousreya A. Hanan N.Rashad A. Molecular docking and anticonvulsant activity of newly synthesized quinazoline derivatives. Molecules. 2017; 22(7):1094.
15. Tony F. Christoph R.Mohammad M. Jannis B.Corina H. Isabel Z. Hanife B.Maria L. Oliver F. Barbara K. Thomas E. Manfred M. Svetlana B. Synthesis of novel hybrids of quinazoline and artemisinin with high activities against Plasmodium falciparum, Human Cytomegalovirus, and Leukemia Cells. ACS Omega. 2017; 2(6):2422-2431.
16. Al-Mulla A. A review: Biological importance of heterocyclic compounds. Der Pharma Chemica. 9(13):141-147 (2017).
17. Amit B.Investigation of the antibacterial activity of new quinazoline derivatives against methicillin and quinolone resistant Staphylococcus aureus. J.Chem. Res. 2020; 44(5):315-321.
18. Kajal P. Poonam K. Vishal S. Synthesis of Quinazoline derivatives and its Antimicrobial Activity. Research J. Pharm. and Tech. 2017; 10(8): 2611-2613. doi: 10.5958/0974-360X.2017.00463.2
19. K. Girija K. Sathiyaraj S. Rajendiran V. Hemalatha K. 2, 3-Disubstituted Quinazolinones: Study of its Anti-microbial Activity. Research J. Pharm. and Tech. 2017; 10(4): 1020-1024. doi: 10.5958/0974-360X.2017.00184.6
20. Held F. Guryev A. Frohlich T. et al. Facile access to potent antiviral quinazoline heterocycles with fluorescence properties via merging metal-free domino reactions. Nat Commun. 2017; 8, 15071.
21. Kubacka M. Zadrozna M. Nowak B. et al. Reversal of cardiac, vascular, and renal dysfunction by non-quinazoline α1-adrenolytics in DOCA-salt hypertensive rats: a comparison with prazosin, a quinazoline-based α1-adrenoceptor antagonist. Hypertens Res. 2019; 42,1125-1141.
22. Simranpreet K. Bharti S. Pooja A. Medicinal perspective of quinazolinone derivatives: Recent developments and structure–activity relationship studies. J. Het. Chem. 2022; 59 (2): 239-257.
23. Benoit L. Yuichiro A. Atsuko O. Sandra D. Leonardo L. et al. Discovery and structure–activity relationships of quinazolinone-2-carboxamide derivatives as novel orally efficacious antimalarials. J. Med. Chem. 2021; 64(17): 12582-12602.
24. Parameshwar N.Krishnamurthy G.Jithendra K.Sunil K.Sathish N. Anti-inflammatory, antibacterial and molecular docking studies of novel spiro-piperidine quinazolinone derivatives. J. Taibah Uni. Sci. 2017; 11 (3): 497-511.
25. Rekha T. Siva S.Zyryanov G. Sravya G. Bakthavatchala R. Padmaja A. Synthesis, antimicrobial and antioxidant activities of pyrimidinyl benzothiazine carboxamides. Chemistry Select. 2019; 4 (22): 6813-6820.
26. Angie M. Chee W. Anjan D.Hye J.Kyra W.Lendl T.Melissa L.Amy J. Ruby P. Mark S.Vicky M.Nicholas P.Tomislav K. Mark A. T.and Matthew A. Design, synthesis, and biological evaluation of 2-Nitroimidazopyrazin-one/-es with antitubercular andantiparasitic activity. J.Med.Chem. 2018; 61,11349-11371.
27. Andrzej Z. Malgorzata L.Aleksander S. Anna N.Dariusz K. Synthesis and in vitro antiproliferative activity of novel phenyl ring-substituted 5-alkyl-12(h)-quino[3,4-b][1,4]benzothiazine derivatives. Molecules. 2016;21(11), 1455.
28. Sana A. Fang W. Matloob A. Ameer F. Asim M. Azhar R. Liwu F.Benzothiazine based acetohydrazides and acetamides as anticancer agents. Pak. J. Pharm. Sci. 2019; 32(6):2795-2800.
29. Siva S. Rekha T. Padmaja A. Padmavathi V. Siva K. Kondaiah P. Synthesis, cytotoxic and antioxidant activities of azolyl benzothiazine carboxamides. Res. Chem. Intermed. 2019; 45, 3053-3075.
30. Neethu R. Sreelakshmi N. Jisni R. Leena K. A Review on Synthesis of Benzothiazine Analogues. Research J. Pharm. and Tech. 2017; 10(6): 1791-1797. doi: 10.5958/0974-360X.2017.00316.X
31. Rai A. Singh A. Raj V. Saha S.1,4-benzothiazines- a biologically attractive scaffold. Mini. Rev. Med. Chem. 2018; 18(1): 42-57
32. Pooja Kumari, Umakant, Gyanendra Sharma. Synthesis and Antibacterial activity of some newer Benzimidazole derivatives. Research J. Pharm. and Tech. 2020; 13(6):2597-2600. doi: 10.5958/0974-360X.2020.00462.X
33. Endale M. Yoseph S. Synthesis of benzimidazole-sulfonyl derivatives and their biological activities. Biochem. Res. Int. 2022; Article ID 7255299, 13.