Document Type : Research Paper

Authors

1 Department of Chemistry, College of Science, University of Anbar, Anbar, Iraq

2 Department of Chemistry, College of Science, Tikrit University, Tikrit, Iraq

3 Department of Chemistry, College Ibn-Al-Haitham, Baghdad, Iraq

Abstract

New 2, 3-substituted benzooxazin-4-one derivatives were prepared by means of a altered step by step proceedings in which Schiff bases were substituted with salicylic acid for a ring forming reaction. The compositions of the synthesized compounds were certain via methods spectrometry as elemental analysis, FT-IR, 13C-NMR & 1H-NMR spectral analysis. The bio-activities for the prepared compounds in-vitro as antibacterial and antifungal were estimated as opposed to two races of gram-positive & two races of gram-negative bacteria as parallel to Cefotaxime sodium as regular drug and assessed versus two types of fungi. The prepared compounds were got to have antimicrobial activities spreading from middling to perfect against of the bacteria strains with good percentage mycelial growth inhibition activity against fungi. Molecular docking displays the critical part while effect of variety of substituents on biological activity while mark the disadvantageous constitutional parameters in drawing medication: A different substitution does ensure additional efficiency in bioactivity.
 

 

Keywords

Main Subjects

[1]  Gabbas, A.U.G., Ahmad, M.B., Zainuddin, N. and Ibrahim, N.A. (2016). Synthesis and antimicrobial evaluation of new 3,4-dihydro-2H-nenzo-and naphtho- 1, 3-oxazine derivatives, Rasayan  J. Chem., Vol.9, no.1, pp.1-7.
[2]  Zilong,T., Zhonghua, Z., Zanwen, X., Hanwen, L., Jinwen, C., Wenjing, X.,  and Xiaoming, O. (2012).  Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines, Molecules, Vol. 17, no.7, pp. 8174–8185.
[3]    Akerbladh, L., Chow, S.Y., Odell, L.R. and Larhed, M. (2017).  Synthesis of 4H-Benzo [e][1,3]oxazin-4-ones by a Carbonylation–Cyclization Domino Reaction of ortho-Halophenols and Cyanamide, Chemistry Open, Vol. 6, no. 5, pp.620-628.
[4]    Aibibuli, Z., Wang, Y., Tu, H., Huang, X. and Zhang, A. (2012).  Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents, Molecules, Vol. 17, no. 3, pp.3181-3201.
[5]    Khan, Z.A., Naqvi, S.A.R., Shahzad, S.A., Mohmood, N., Yar, M. and Zahoor, A.F. (2013). Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones, Asian Journal of Chemistry, Vol. 25, no. 1, pp.152-156.
[6]    Kandale, A., Ohlyan, R. and Kumar, G.(2014).  Synthesis and in-vitro antiproliferative activity of 2,3-aryl substituted 1,3-benzoxazin-4-one derivatives, Int. J. Pharm. Sci., Vol. 6, no. 7, pp. 68-71.
[7]   Varshney, H., Ahmed, A., Rauf, A., Husain, F.M. and Ahmed, I.(2017).  Synthesis and antimicrobial evalution of fatty chain substituted 2,5-dimethylpyrrole and 1,3-benzoxazin-4-one derivative, Journal of Saudi Chemistry Society, Vol. 21, no. 1, pp. S394-S402.
[8] El-Sewy, W.S., Mohamed, N.A., Kassem, E.M.M., Mahmoud, K. and Mounier, M.M. (2016).  Synthesis, Biological evaluation and Docking analysis of some novel Quinazolin derivatives as antitumor agents, Iranian Journal of Pharmaceutical Research, Vol. 15, no.1, pp. 179-196.
[9]   El-Mekabaty, A. (2013). Chemistry of 4H-3,1-Benzoxazin-4-ones, Int. J. Modern Org. Chem., Vol. 2, no. 2, pp. 81-121.
 [10] El-Hashash, M.A., Azab, M.E., Faty, R.A. and Amr, A.E ( 2016).  Synthesis, antimicrobial and anti-inflammatory activity of some new benzoxazine and quinazoline candidates, Chem. Pharm. Bull., Vol. 64, no. 3, pp. 264-271.
[11]  Abu-Ragheef, Z.A.J., Ph.D. thesis. (2017). Design, Synthesis, Characterization and Antimicrobail studies of new [Azonenzen-p,p’-di(3-substituted 4(3H) quinazolin-4-one, 4-Thio and 4-Substituted quinazolin-2-yl] derivatives from new Azobenzen-p,p’-di(3,1-benzoxazin-4-one-2-yl) compounds, University of Baghdad.
[12]  Zhang, K., and Ishida, H. (2015). Smart Synthesis of High-Performance Thermosets Based on ortho- (amideco-imide) Functional Benzoxazines, Frontiers in Materials, Vol. 2, no. 5, pp. 1-27.
[13] Salama, M.M., Ahmed, S.G. and Hassan, S.S. (2017). Synthesis, Characterizations, Biological, and Molecular Docking studies of some amino acid Schiff bases with their Cobalt(II) complexes, Advances in Biological Chemistry, Vol. 7, pp. 182-194.
[14] Aljamali, N.M. (2014). Synthesis and Bio-chemical investigation of series of Bis-(Aldamine-sugar), Int. J. Pharm. Pharmacol., Vol. 3, no. 2, pp. 149-153.
[15] Schoenknecht, F.D. (1973). The Kirby-Bauer Technique in Clinical Medicine and Its Application to Carbenicillin, The Journal of Infectious Diseases, Vol. 127, pp. S111-S115.
[16] Hadizadch, I., Peivastegan, B. and Kolahi, M. (2009) Antifungal activity of Nettle (Urtica dioica L.), Colocynth (Citrullus colocyuthis L. Schrad), Oleander (Nerium oleander L.) and Konar (Ziziphus spina-christi L.) Extracts on Plants Pathogenic Fungi, Pak. J. Biol. Sci., Vol. 12, no. 1, pp. 58-63.
[17] Tanoli, S.A., Tanoli, N.U., Usmani, S., and Ferreira, A.G. (2014). The exploration of interaction studies of smaller size, mostly ignored yet intrinsically inestimable molecules towards BSA; An example of STD and DOSY NMR, Cent. Eur. J. Chem., Vol. 12, pp. 332–340.
[18] Mabkhot, Y., Aldawsari, F., Al-Showiman, S., Barakat, A., Hadda, T., Mubarak, Naz, S., Ul-Haq, Z., and Rauf, A. (2015).  Synthesis, Bioactivity, Molecular Docking and POM Analyses of Novel Substituted Thieno[2,3-b]thiophenes and Related Congeners, Molecules, Vol. 20, no. 2, pp. 1824–1841.
[19] Thangavelu, P., Chellappa, S. and Thangavel, S. (2018). Synthesis, Evaluation and Docking studies of Novel Formazan derivatives as an Enoyl-ACP reductase inhibitors, Int.  J.  Pharm Pharm. Sci., Vol. 10, no. 8, pp. 56-61.
[20] Mondoza-Figueroa, H. L., Serrano-Alva, M. T., Aparicio-Ozores, G., Martinez-Gudino, G., Suarez-Castillo, O.R., Perez-Rojas, N.A., and Morales-Rios, M.S., 2018 "Synthesis, antimicrobial activity, and molecular docking study of fluorine-substituted indole-based imidazolines", Medicinal Chemistry Research, Vol. 27, no., PP. 1624-1633.