Synthesis, Characterization, and Computational, Biological Studies of Four-membered Cyclic Amides 2- azetinones
Subject Areas : Journal of Chemical Health Risks
1 - Department of Chemistry, College of Science, University of Thi-Qar, Iraq
Keywords: β-Lactams, Azetidin-2-ones, Tetrahydro furan-3-carboxylic acid, Gaussian program,
Abstract :
Two compounds,3-benzoyl-2-(4-bromophenyl)-3-phenyl-6 – oxa-2-azaspiro[3.4]octan-1-one and 1',1'''-bis(3-bromo-4-(dimethylamino)phenyl)-4,4'''',5,5''''-tetrahydro-2H,2''''H-tetraspiro[furan-3,2'-azetidine-4',1''-acenaphthylene-2'',2'''-azetidine-3''',3''''-furan]-3',4'''-dione, were synthesized by tetrahydro furan-3-carboxylic acid and appropriate imines. Two studies were conducted on the prepared compounds, one of them is the study of their anti-biological efficacy using two types of bacteria Staphylococcus aureus and Escherichia coli, The other study that was conducted on the compounds is a computational study to calculate some of the thermodynamic parameters of synthesized derivatives by using a Gaussian program.
4. Mechergui A., Touati A., Baaboura R., Achour W., Hassen A.B., 2011. Phenotypic and molecular characterization of β-lactams resistance in commensal Neisseria strains isolated from neutropenic patients in Tunisia.AnnalMicr.61, 695–697.
6- Banik I., Becker F.F.; Banik B.K., 2003.Stereoselective Synthesis of β-Lactams with Polyaromatic Imines: Entry to New and Novel Anticancer Agents. J Med Chem. 46, 12-15.
9. Reddy R., Saravanan P., Corey J., 2004.A Simple Stereo controlled Synthesis of Salinosporamide A. J Am Chem Soc. 126, 6230- 6231.
10. Turos E., Coates C., Shim J., Wang Y. Leslie M., Long T., Kumar S., Alex O., Marci C., Sonja D., Daniel V., Eduardo A., Javier G., 2005. N-Methylthio β-lactam antibacterials: Effects of the C3/C4 ring substituents on anti-MRSA activity Bioorg. Med. Chem., 13, 6289-6308.
11. Jarrahpour A., Shekarriz M., Taslimi A., 2004. Synthesis and Antimicrobial Activity of Some New Sugar-Based Monocyclic β-Lactams. Molecules. 9, 29.
12. Ali R., 2011. Synthesis of New Schiff's Bases Derived from 4-Phthalimidyl Acetophenone. Journal of Al-Nahrain. 14(3), 1-8.
14. Enders D., Gries G., 2005.Asymmetric Synthesis of Substituted Azetidine Type α- and β-Amino Acids, Synthesis. 3508-3516.
15. Maowad E.B., 1989. Synthesis of some new heterocyclic compounds with expected potential biological activity, J Islamic AcadSci. 24, 237-240.
16. Sajda S. Afatt., Muntaha Y., Ibrahim A., 2016. Syntheses, Characterization of a New Ligand(3-Hydrazino-N-isopropylidene-5-methyl-4H-1,2,4-trizole-4-amine) and its complex with (Fe(III), Co(III) and Ni(II)), Journal of Thi-Qar Science. 5(4), 1991- 8690.
18.Saranya M., Ayyappan S., Nithya R., Sangeetha K., Gokila A., 2018. Molecular structure, NBO and HOMO-LUMO analysis of quercetin on single layer grapheme by density functional theory. Molecular Structure. 13(1), 97–105.
19. Bendjeddou A., Abbaz T., Drissi S., Gouasmia A., Villemin D., 2016.Quantum chemical studies on molecular structure and reactivity descriptors of a series of trimethyltetrathiafulvalene functionalized by conjugated substituent. J Adv Chem Scie. 318 - 322.
20. Nowotny J., Bak T., Nowotny K., Sheppard R., 2008. Defect Chemistry and Electrical Properties of Titanium Dioxide. 1. Defect Diagrams, J Phys Chem C. 112(2), 590-601.
21. Jensen F., 2017.Introduction to computational chemistry, John Wiley & sons. ISBN: 978-1-118-82599-0.3rd Edition. pp. 664.
22.Gotwals R., Sendlinger C., 2007.The North Carolina School of Science and Mathematics, Durham, NC.