Preparation, Characterization and Antibacterial Activity of some New Oxazolidin-5-one Derivatives Derived from Imine Compounds
محورهای موضوعی :
Rasim Farraj Muslim
1
,
Ismaeel Majeed
2
,
Suheb Eaid Saleh
3
,
Marwan Mahmood Saleh
4
,
Mustafa Nadhim Owaid
5
,
Jalal Abdulkareem Abbas
6
1 - Department of Environmental Sciences, College of Applied Sciences-Hit, University of Anbar, Hit, Anbar, Iraq
2 - Department of chemistry, College of education for pure science-Ibn Al-Haitham University of Baghdad, Baghdad, Iraq
3 - Directorate of Education in Anbar, Ministry of Education, Ramadi, Anbar 31001, Iraq
4 - Department of Biophysics, College of Applied Sciences-Hit, University of Anbar, Hit, Anbar, Iraq
5 - Department of Heet Education, Directorate of Education in Anbar, Ministry of Education, Hit, Anbar, Iraq
6 - Department of Chemistry, Faculty of Science, Gazi University, Teknikokullar, Ankara, Turkey
تاریخ دریافت : 1400/07/03
تاریخ پذیرش : 1400/09/06
تاریخ انتشار : 1401/09/10
کلید واژه:
Biological activity,
Heterocyclic,
Oxazolidine-5-one,
MICs,
چکیده مقاله :
In this research, 5- membered heterocyclic compounds as oxazolidine-5-one J1-J5 derivatives were prepared using primary aromatic amine, aromatic carbonyl compounds and chloroacetic acid. By combining primary aromatic amines and aromatic carbonyl compounds, Schiff's bases were synthesized. Schiff bases are used with the chloroacetic acid compound to prepare oxazolidine-5-one J1-J5 derivatives. The compounds J1-J5 were described using NMR spectroscopy and FT-IR. .The biological efficacy was evaluated according to maximum inhibitory concentrations (MICs) toward Staphyloccoccus aureus and Esherichia coli. The best MIC was 210 μg ml-1 for J4 against the two pathogenic bacteria, while J1, J4, and J1 did not show any inhibitory effect against all bacteria. Finally, the best chemical created, 3'-(pyrimidin-2-yl) spiro[indoline-3,2'-oxazolidine]-2,5'-dione (J4), inhibited the development of both gram-negative and positive bacteria.
منابع و مأخذ:
Mumtaz A., Mahmud T., Elsegood M.RJ., 2016. Synthesis and Characterization of New Schiff Base Transition Metal Complexes Derived from Drug Together with Biological Potential Study. J Nucl Med Radiat Ther. 7(6), DOI: 10.4172/2155-9619.1000310.
Abid O.H., Tawfeeq H.M., Muslim R.F., 2017. Synthesis and characterization of novel 1,3-oxazepin-5(1H)-one derivatives via reaction of imine compounds with isobenzofuran-1(3H)-one. Acta Pharm. Sci. 55, 43–55.
Jiang M., Ni X.W., 2018. Effects of water and temperature on reaction mechanism and crystal properties in a reactive crystallization of paracetamol. Chem Eng Process. Process Intensif. 131, 20–26.
Muslim R.F., Tawfeeq H.M., Owaid M.N., Abid O.H., 2018. Synthesis, characterization and evaluation of antifungal activity of seven-membered heterocycles. Acta Pharm Sci. 56, 39–57.
Ebrahimi Z., Davoodnia A., Motavalizadehkakhky J.M., 2020. Synthesis, characterization, and molecular structure investigation of new tetrahydrobenzo[b]thiophene-based Schiff bases: A combined experimental and theoretical study. Eurasian Chem. Commun. 98, 170–180.
Iqbal A., Siddiqui H.L., Ashraf C.M., Ahmad M., Weaver G.W., 2007. Synthesis, characterization and antibacterial activity of azomethine derivatives derived from 2-formylphenoxyacetic acid. Molecules. 12, 245–254.
Makawana J.A., Sangani C.B., Lin L., Zhu H.L., 2014. Schiff’s base derivatives bearing nitroimidazole and quinoline nuclei: New class of anticancer agents and potential EGFR tyrosine kinase inhibitors. Bioorganic Med Chem Lett. 24, 1734–1736.
Anouar E.H., Raweh S., Bayach I., Taha M., Baharudin M.S., Di Meo F., Hasan M.H., Adam A., Ismail N.H., Weber J.F.F., Trouillas P., 2013. Antioxidant properties of phenolic Schiff bases: Structure-activity relationship and mechanism of action. J. Comput Aided Mol Des. 27, 951–964.
Taha M., Ismail N.H., Jamil W., Yousuf S., Jaafar F.M., Ali M.I., Kashif S.M., Hussain E., 2013. Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones. Molecules. 18, 10912–10929.
Aslam M.A.S., Mahmood S.U., Shahid M., Saeed A., Iqbal J., 2011. Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors. Eur J Med Chem. 46, 5473–5479.
Nath M., Saini P.K., Kumar A., 2010. New di- and triorganotin(IV) complexes of tripodal Schiff base ligand containing three imidazole arms: Synthesis, structural characterization, anti-inflammatory activity and thermal studies. J Organomet Chem. 695, 1353–1362.
Rakesh K.P., Manukumar H.M., Gowda D.C., 2015. Schiff’s bases of quinazolinone derivatives: Synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants. Bioorganic Med Chem Lett. 25, 1072–1077.
Taha M., Naz H., Rasheed S., Ismail N.H., Rahman A.A., Yousuf S., Choudhary M.I., 2014. Synthesis of 4-methoxybenzoylhydrazones and evaluation of their antiglycation activity. Molecules. 19, 1286–1301.
Wang Y.Y., Xu F.Z., Zhu Y.Y., Song B., Luo D., Yu G., Chen S., Xue W., Wu J., 2018. Pyrazolo[3,4-d]pyrimidine derivatives containing a Schiff base moiety as potential antiviral agents. Bioorganic Med Chem Lett. 28, 2979–2984.
Al-Abed Y., Dubrovsky L., Ruzsicska B., Seepersaud M., Bukrinsky M., 2002. Inhibition of HIV-1 nuclear import via Schiff base formation with arylene bis(methylketone) compounds. Bioorganic Med Chem Lett. 12, 3117–3119.
Shebl M., Adly O.M.I., Abdelrhman E.M., El-Shetary B.A., 2017. Binary and ternary copper(II) complexes of a new Schiff base ligand derived from 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone: Synthesis, spectral, thermal, antimicrobial and antitumor studies. J Mol Struct. 1145, 329–338.
Zhang K., Wang P., Xuan L.N., Fu X.Y., Jing F., Li S., Liu Y.M., Chen B.Q., 2014. Synthesis and antitumor activities of novel hybrid molecules containing 1,3,4-oxadiazole and 1,3,4-thiadiazole bearing Schiff base moiety. Bioorganic Med Chem Lett. 24, 5154–5156.
Murtaza S., Akhtar M.S., Kanwal F., Abbas A., Ashiq S., Shamim S., 2017. Synthesis and biological evaluation of schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent. J Saudi Chem Soc. 21, S359–S372.
Prasanna Kumar B.N., Mohana K.N., Mallesha L., 2013. Synthesis and antiproliferative activity of some new fluorinated Schiff bases derived from 1,2,4-triazoles. J Fluor Chem. 156, 15–20.
Song W.J., Cheng J.P., Jiang D.H., Guo L., Cai M.F., Yang H.B., Lin Q.Y., 2014. Synthesis, interaction with DNA and antiproliferative activities of two novel Cu(II) complexes with Schiff base of benzimidazole. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 121, 70–76.
Da Silva C.M., Da Silva D.L., Modolo L.V., Alves R.B., De Resende M.A., Martins C.V.B., De Fátima Â., 2011. Schiff bases: A short review of their antimicrobial activities. J Adv Res. 2, 1–8.
Jesmin M., Ali M.M., Khanam J.A., 2010. Antitumour activities of some schiff bases derived from benzoin, salicylaldehyde, amino phenol and 2,4 dinitrophenyl hydrazine. Thai J Pharm Sci. 34, 20–31.
Sunil D., Isloor A.M., Shetty P., Nayak P.G., Pai K.S.R., 2013. In vivo anticancer and histopathology studies of Schiff bases on Ehrlich ascitic carcinoma cells. 1st Cancer Update. Arab J Chem. 6, 25–33.
Hussain M.R.A.T.S., 2017. Synthesis and Characterization of Five Member Ring Heterocyclic Derivatives Compounds. Int J Sci Res. 6, 1060–1066.
Anupama B., Lakshmi K.C., Sindhura J.N., 2015. Microwave assisted synthesis of 4-substituted polyhydroxidene-2-phenyl oxazolidine-5-ones. 4, 1478–1487.
Hagel D., Paneth A., Plech T., 2014. Synthesis, Characterization and Antimicrobial Activity of 4-Benzoyl-1-(pyrazin-2-ylcarbonyl)-thiosemicarbazide. J Single Mol Res. 3, 541–549.
Dey T., Jacob J., Sahu S., Baidya M., 2011. Synthesis and oral hypoglycemic activity of pyrazoloxazolidinediones. Pharmacologyonline. 1, 908–916.
28-. Satyanarayana V.S.V., Sreevani P., Sivakumar A., Vijayakumar V., 2008. Synthesis and antimicrobial activity of new Schiff bases containing coumarin moiety and their spectral characterization. Arkivoc. 221–233.
Shankarananth V., Ranganayakulu D., C.Sridhar D.K.K.R., 2012. Synthesis and Antiinflammatory activity of some oxazolidinedione derivativ. J Pharm Res. 5, 1633–1635.
Ayfan A.K.H., Muslim R.F., Noori N.S., 2019. Preparation and characterization of novel disubstituted 1,3- oxazepine-tetra-one from schiff bases reaction with 3-methylfuran-2,5-dione and 3-phenyldihydrofuran-2,5-dione. Res J Pharm Technol. 12, 1008–1016.
Tawfeeq H.M., Muslim R.F., Abid O.H., Owaid M.N., 2019b. Synthesis and characterization of novel tetrazole derivatives and evaluation of their anti-candidal activity. Acta Pharm Sci. 57, 45–63.
Tawfeeq H.M., Muslim R.F., Abid O.H., Owaid M.N., 2019a. Synthesis and characterization of novel five-membered heterocycles and their activity against Candida yeasts. Acta Chim Slov. 66, 552–559.
Wade L.G., Simek J.W., 2013. Solutions Manual for Organic Chemistry: Pearson New International Edition. Pearson Higher Ed.
Mcdonnell G., Russell A.D., 1999. Antiseptics and disinfectants: Activity, action, and resistance. Clin Microbiol Rev. 12, 147–179.
El-Shehry M.F., El Telbani E.M., Hegab M.I., 2018. Synthesis of cyclic and acyclic pyrimidine nucleosides analogues with anticipated antiviral activity. Acta Chim. Slov. 65, 1–6.
Elshehry M.F., Balzarini J., Meier C., 2009. Synthesis of new cyclic and acyclic 5-halouridine derivatives as potential antiviral agents. Synthesis (Stuttg). 841–847.
El Shehry M.F., Abu-Hashem A.A., El-Telbani E.M., 2010. Synthesis of 3-((2,4-dichlorophenoxy)methyl)-1,2,4-triazolo(thiadiazoles and thiadiazines) as anti-inflammatory and molluscicidal agents. Eur J Med Chem. 45, 1906–1911.
Ahmed R., Majeed I., Ahmed,A., Yousif E., Al-Jeboori M., 2016. Formation of new metal complexes with benzene triazole and thiadiazole-based Schiff-bases. ChemXpress. 9, 61–68.
Ibtisam K., 2009. Synthesis of some new ,3-oxazepine derivatives and evaluation of antibacterial activitv. Tikrit lournal Pltarmuceutical Sci. 5, 147–155.
