Microwave Assisted Synthesis of Pyromellitdiimide Bis Schiff Bases and Evaluation of Their Antimicrobial Activity
Keywords:
Pyromellitdiimide, Bis Schiff base, Fusion process, Microwave, AntimicrobialAbstract
The present work involved synthesis a series of new pyromellitdiimide bearing two Schiff base components through performing several steps. Compound (1) was synthesized in first step, N, N`-bis[(4- acetophenyl)pyromellitamic acid] through reaction two moles of 4-amino acetophenone with pyromellitic anhydride in acetone solvent with stirring for two hours. Compound (1) was dehydrated in the second step by fusion process in sand bath for two hours affording compound (2), N, N-bis[(4- acetophenyl)pyromellitdiimide]. Third step involved adding compound (2) in acid_ catalyzed condensation reaction with various primary aromatic amines under the influence of microwave irradiation for (10-15) minutes producing the target bis Schiff bases (3-6), this technique has many advantages it is simple, safe, clean, very fast with high yields unlike traditional method that are costly and risky. Based on spectroscopic data FTIR, 1H-NMR and 13C-NMR, the structures of newly synthesized bisschiff bases were confirmed. Results of antimicrobial activity screening of compounds (3-6) indicated that most of them showed potent activity against gram positive bacteria (staphylococcus aureus), gram negative bacteria (E-Coli) and type of fungi (candida albicans), compounds (3) and (4) had strong inhibition against bacteria but weak inhibition against fungi since compounds (5) and (6) had strong inhibition against bacteria and moderate inhibition against fungi.
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References
abdulrasool,J. M., Ali, E. T. &Tomma, J. H. 2017. NewSchiff-Bases Prepared
From Pyromellitic Dianhydride Via Its Hydrazide Derivative. Ibn ALHaitham Journal For Pure and Applied Science, 29.
Al-Azzawi, A. M. &Jassem, E. K. 2016. Synthesis and characterization of
several new succinimides linked to phenyl azo benzothiazole or
thiazole moieties with expected biological activity. Iraqi Journal of
Science, 534-544.
Al-Azzawi, A. &A1-Obiadi, K. 2016. Synthesis and anti-microbial
screening of new bisschiff bases and their acetyl oxadiazole
azetidinone derivatives derived from pyromelliticdiimide. Int. J. Res.
Pharm. Chern, 6, 1-8.
Al-Azzawi, A. M. &Hassan, A. S. A. 2014. Synthesis and antimicrobial
activity of new succinimides bearing different heterocycles.
International Journal of Research in pharmacy and chemistry, 4, 755-
Al-Azzawi, A. M. &Mahdi, S. A. R. 2013. Synthesis and Evaluation of
Antimicrobial activity of several new Maleimides to Benzothiazole
moiety. Baghdad Science Journal, 10, 658.
Al-Azzawi, A. M. &Raheem, A. A. A.-K. 2017.Synthesis and antibacterial
screening of new Schiff bases based on N-(4-acetophenyl)
succinimide. Iraqi Journal of Science, 1790-1801.
Bandyopadhyay, D., Layek, M., Fleck, M., Saha, R. & Rizzoli, C. 2017.
Synthesis, crystal structure and antibacterial activity of azido
complexes of cobalt (III) containing heteroaromatic Schiff bases.
Inorganica Chimica Acta, 461, 174-182.
https://doi.org/10.1016/j.ica.2017.02.018
Borchhardt, D. & Andricopulo, A. D. 2009. CoMFA and CoMSIA 3D
QSAR models for a series of cyclic imides with analgesic activity.
Medicinal Chemistry, 5, 66-73.
El-Gammal, O. A., Alshater, H. & El-Boraey, H. A. 2019.Schiff base metal
complexes of 4-methyl-lH-indol-3-carbaldehyde derivative as a
series of potential antioxidants and antimicrobial: Synthesis,
spectroscopic characterization and 3D molecular modeling. Journal
of Molecular Structure, 1195, 220-230.
.https://doi.org/10.1016/j.molstruc.2019.05.101
El-Gammal, O. A., Mohamed, F. S., Rezk, G. N. & El-Bindary, A. A. 2021.
Synthesis, characterization, catalytic, DNA binding and antibacterial
activities of Co (II), Ni (II) and Cu (II) complexes with new Schiff
base ligand. Journal of Molecular Liquids, 326, 115223.
.https://doi.org/10.1016/j.molliq.2020.115223
Fadel, Z. H. & Al-Azzawi, A. M. 2021. Design, synthesis and antibacterial
activity screening of novel bis cyclic imides linked to trimethoprim
drug. Research Journal of Pharmacy and Technology, 14, 5874-5880.
.http://dx.doi.org/10.52711/0974-360X.2021.01049
Fadel, Z. H. & Al-Azzawi, A. M. 2022. Designing and Synthesising Novel
Benzophenone Biscyclic Imides Comprising Drug Moity with
Investigating their Antimicrobial Activity. Baghdad Science Journal, 19,
-1027 http://dx.doi.org/10.21123/bsj.2022.19.4.ID0000
Kadhim, A. K. & Khalaf, M. I. 2023. A Core-extended Pyromellitic
Diimide as A p-Channel Semiconductor.J. Med. Chern. Sci., 2023,
(1) 62-70 https://doi.Org/10.26655/JMCHEMSCI.2023.l.8
Kumar, A., Kumar, N., Roy, P., Sondhi, S. & Sharma, A. 2015. Synthesis
of acridine cyclic imide hybrid molecules and their evaluation for
anticancer activity. Medicinal Chemistry Research, 24, 3272-
https://doi.org/10.1007/s00044-015-1380-2
Rakesh, K., Manukumar, H. & Gowda, D. C. 2015. Schiffs bases of
quinazolinone derivatives: Synthesis and SAR studies of a novel
series of potential anti-inflammatory and antioxidants. Bioorganic &
medicinal chemistry letters, 25, 1072-1077.
https://doi.org/10.1016/j.bmcl.2015.01.010
Saleem, S. S., Sankarganesh, M., Jose, P. A. & Raja, J. D. 2021. Design,
synthesis, antioxidant, antimicrobial, DNA binding and molecular
docking studies of morpholine based Schiff base ligand and its metal
(II) complexes. Inorganic Chemistry Communications, 124, 108396.
https://doi.org/10.1016/j.inoche.2020.108396
Satyanarayana, V., Sreevani, P., Sivakumar, A. & Vijayakumar, V. 2008.
Synthesis and antimicrobial activity of new Schiff bases containing
coumarin moiety and their spectral characterization. Arkivoc, 17,
-233.
Shinde, A., Zangade, S., Chavan, S. & Vibhute, Y. 2014. Microwave
induced synthesis of bis-Schiff bases from propane-1, 3-diamine as
promising antimicrobial analogs. Organic Communications, 7, 60.
Sondhi, S. M., Rani, R., Singh, J., Roy, P., Agrawal, S. & Saxena, A. 2010.
Solvent free synthesis, anti-inflammatory and anticancer activity
evaluation of tricyclic and tetracyclic benzimidazole derivatives.
Bioorganic & medicinal chemistry letters, 20, 2306-
https://doi.org/10.1016/j.bmcl.2008.07.048
Taha, N. I., Tapabashi, N. O. & El-Subeyhi, M. N. 2018. Green synthesis of
new tetra schiff bases and bis-azo bis-schiff bases derived from 2, 6-
diaminopyridine as promising photosensitizers. International Journal
of Organic Chemistry, 8, 309-318.
https://doi.org/10.4236/ijoc.2018.83023
Teng, B., Zheng, J., Huang, H. & Huang, P. 2011.Enantioselective synthesis
of glutarimide alkaloids cordiarimides A, B, crotonimides A, B, and
julocrotine. Chinese Journal of Chemistry, 29, 1312-1318.
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