Synthesis and Characterization of some 2-Azetidinones Derived from 3-Nitro Phthalic Anhydride and Evaluation their Biological against Bacteria and Fungi

Abstract:

Reaction of the moiety 3-nitro phthalic anhydride with p- Phenylene diamine in (40 ml) acetic acid to give compound (p-amino phenyl)-3-nitro phthalimide (A₁).Which that react with different aromatic aldehyde in ethanol absolute to give compounds hydrazone (A₂-A₅), then react this compounds (A₂-A₅) with chloro acetyl chloride in presence of TEA by using DMF as solvent to obtain 2-azetidinones (A₆-A₉).The compounds of all the newly synthesized structures were confirmed by and ,IR, ¹H NMR as well as melting point. Some of these new structures showed antimicrobial activity (A₇-A₈) and anti-bacterial activity (A₇-A₈).Antibacterial activity of some prepared compounds against two types of bacteria: Staphylococcus aureus (Gram positive) and E.coli (Gram negative). Some the compounds showed high inhibition activity against bacteria and two fungi (Candida albicans) and (Candida tropicalis.).

• Periodical: Materials Science Forum (Volume 1002)
• Pages: 360-368
• DOI: https://doi.org/10.4028/www.scientific.net/MSF.1002.360
• Online since: July 2020
• Authors: Ahmood Kh. Jebur Al-Joubory, Rabiha Hameed Saleh, Omar Abdulrahman Mohammed*
• Keywords: 2-Azetidinones, 3-Nitro Phthalic Anhydride, Heterocyclic Compounds, Schiff Bases

References

[1] N. Kushwaha, D.Kaushik, Recent advances and future prospects of phthalimide derivatives. J App Pharma Sci. 6 (2016) 71-159.

DOI: 10.7324/japs.2016.60330

[2] F. Hassanzadeh, M. Rabbani, A.Fasihi, G. H. Hakimelahi, M. Mohajeri, Synthesis of phthalimide derivatives and evaluation of their anxiolytic activity. Research in Pharmaceutical Sciences. 2(1) (2008) 35-41.

[3] S.Sharma, , A. D. K Jain, A. Aggarwal, N. S. Gill, A review: synthesis and biological activity of imides. the Global Journal of Pharmaceutical Research. 1(3) (2012) 411-421.

[4] D. C. Rosario, D. S. Joe, Antibacterial activity of N-substituted 3 and 4-nitrophthalimides. Proceedings: Plant Sciences. 80 (2) (1974) 68-75.

DOI: 10.1007/bf03050660

[5] A. R Kittleson, To Standard Oil Development Co.",U. S. Patent  2 (1950) 553-770 ;Chem. Abstr. (1951)45-6791.

[6] D. M Badgujar, M. B. Talawar, S. N. Asthana, P. P. Mahulikar, Novel synthesis of biologically active nitro heterocyclic compounds (2008).

[7] R. B. Patel, P. S. Desai, K. R. Desai, K. H. Chikhalia, Synthesis of pyrimidine based thiazolidinones and azetidinones: antimicrobial and antitubercular agents (2006).

DOI: 10.1002/chin.200628143

[8] H.Freddy Havaldar , J. Sushil Kumar Mishra., Synthesis of some azetidi-2-ones and thiazolidin-4- ones as potential antimicrobial Agents. Indian J. Heterocycl., Chem. 13 (2004) 197-200.

[9] M. Omar Abdulrahman, preparation of some heterocyclic derivatives from 2- mercapto benzothiazole and study their effect of bacteria. Journal Biochem. Cell. Arch. Vol. 19, No. 1 (2019) 1717-1721.

[10] J.M. Vanderveen, S. Bari,I. Krishnan M.S. Manhas, A.K. Bose,. J.Org.Chem. (1989) 54- 5758.

[11] A. Bagherwal, A. Baldi, R. K. Nagar, D. K. Patidar, Synthesis and antimicrobial studies of azetidinone derivatives from naphthylamine moiety. Intern. J. Chem. Tech. Res, 3(1) (2011) 274-279.

[12] CLSI . Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically Approved Standard, CLSI Document M7-A7. 7th Ed. ISBN 1-56238, (2006).

[13] N. H. Bansod, G. N Chaudhari, P. Bodade, Indo American, Journal of Pharmaceutical Sciences, 4 (2017) 965-970.