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Investigation of Antimicrobial Effects of Some N-Substituted Phthalimide Derivatives

Year 2024, , 57 - 61, 27.10.2024
https://doi.org/10.5281/zenodo.13996463

Abstract

In this study, antimicrobial effects of some N-substituted phthalimide derivatives (2, 3, 4a-c) were investigated on Gram-negative (generic Escherichia coli, Salmonella enterica Typhimurium, Citrobacter freundii, Klebsiella pneumoniae, shiga toxin producing E. coli O157:H7 (STEC O157:H7)) and Gram-positive bacteria (Stapylococcus aureus, Listeria monocytogenes). The antifungal effects of N-substituted phthalimide derivatives were tested on yeast (Candida albicans) and mold (Aspergillus brasiliensis). In the antimicrobial analysis, vancomycin-30 µg (VA-30), rifampicin-5 µg (RA-5) and tetracycline-30 µg (TE-30) against bacteria and fluconazole-25 µg (FZ-25) against fungi were used as positive control groups. In general, N-substituted phthalimide derivatives (2, 3, 4a-c) have been observed to have important antimicrobial activities on Gram-negative, Gram-positive bacteria, yeast, and mold. Compound 4c, which contains a diethylamine group in its structure, showed the best activity on C. freundii and L. monocytogenes compared to other phthalimide derivatives and control compounds. On the other hand, compound 3 containing Br has been observed to have broad-spectrum antimicrobial properties with both antibacterial and antifungal effects, except for C. freundii. In conclusion, N-substituted phthalimide derivatives (2, 3, 4a-c) can be considered new promising antimicrobial agents.

References

  • [1] Kushwaha, N., Kaushik, D., "Recent advances and future prospects of phthalimide derivatives", Journal of Applied Pharmaceutical Science, Vol. 6, Issue 3, Pages 159-171, 2016.
  • [2] Khokra, S. L., Arora, K., Mehta, H., Aggarwal, A., Yadav, M., "Common methods to synthesize benzothiazole derivatives and their medicinal significance", International Journal of Pharmaceutical Sciences and Research, Vol. 2, Issue 6, Pages 1356-1378, 2011.
  • [3] Pawar, N. S., Patil, J. U., Suryawanshi, K. C., Chaudhary, S. R., Patil, P.B., "An improved microwave irradiation method for synthesis of some new N-alkyl and N-alkyloxy phthalimides", Der Pharma Chemica, Vol. 4, Issue 1, Pages 15-22, 2012.
  • [4] Bhat, M.A., Al-Omar, M.A., Siddiqui, N., "Synthesis, anticonvulsant and neurotoxicity of some novel 1, 3, 4-oxadiazole derivatives of phthalimide", Der Pharma Chemica, Vol. 2, Issue 2, Pages 1-10, 2010.
  • [5] Tan, A., Almaz, Z., "Synthesis, investigation of the cholinesterase inhibitory activities and in silico studies of some novel N-substituted phthalimide derivatives", Journal of the Iranian Chemical Society, Vol. 19, Issue 7, Pages 2833-2844, 2022. (and therein)
  • [6] Al-Qaisi, J.A., Alhussainy, T.M., Qinna, N.A., Matalka, K.Z., Al-Kaissi, E.N., Muhi-Eldeen, Z.A., "Synthesis and pharmacological evaluation of aminoacetylenic isoindoline-1,3-dione derivatives as anti-inflammatory agents", Arabian Journal of Chemistry, Vol. 7, Issue 6, Pages 1024-1030, 2014.
  • [7] Othman, I.M., Gad-Elkareem, M.A., El-Naggar, M., Nossier, E. S., Amr, A.E.G.E., "Novel phthalimide based analogues: Design, synthesis, biological evaluation, and molecular docking studies", Journal of enzyme inhibition and medicinal chemistry, Vol. 34, Issue 1, Pages 1259-1270, 2019.
  • [8] Bansal, R., Karthikeyan, C., Moorthy, N., Trivedi, P., "QSAR analysis of some phthalimide analogues based inhibitors of HIV-1 integrase", Arkivoc, Vol. 15, Issue xv, Pages 66-81, 2007.
  • [9] Patil, M., Rajput. S., “Synthesis and antimicrobial evaluation of some novel diazo derivative of cyclic Imides using diazotization coupling reaction”, Chemical science review and letters, Vol. 5, Issue 17, Pages 46-52, 2016.
  • [10] Kumari, S., Gupta, V, Singh, S. Gupta, Y., "Synthesis, “Characterization and antimicrobial activities of five and six member cyclic imides derivatives”, Research Journal of Science and Technology, Vol. 11, Issue 1, Pages 82-86, 2019.
  • [11] Stiz, D., Corrêa, R., Dauria, F., Simonetti, G., Cechinel-Filho, V., “Synthesis of cyclic imides (Methylphtalimides, carboxylic acid phtalimides and itaconimides) and evaluation of their antifungal potential”, Medicinal Chemistry, Vol. 12, Issue 7, Pages 647- 654, 2016.
  • [12] Chaudhari, P., Rajput, S., “One pot synthesis and antimicrobial evaluation of some novel bis-chalcones and pyrazoles from cyclic imides under microwave irradiation”, World Journal of Pharmaceutical Research, Vol. 5, Issue 8, Pages 1301-1313, 2016.
  • [13] Ahmed, W.S., Mahmood, A.A.R., Al-Bayati, R.I., “Synthesis and evaluation of antimicrobial activity of new imides and schiff bases derived from ethyl-4-amino benzoate”, Oriental Journal of Chemistry, Vol. 34, Issue 5, 2018.
  • [14] Baluja, S., Chanda, S., Chavda, K., “Synthesis, characterization and in vitro antimicrobial activity of cyclic imide: Isoindoline-1, 3-dione derivatives”, GSC Biological and Pharmaceutical Sciences, Vol. 10, Issue 1, Pages 046-058, 2020.
  • [15] Fekambaram, D., Santhy, K., "Phytochemical characterization and assessment of hygrophila auriculata (buch.-ham) leaves for antioxidant and antimicrobial activity", Indian Journal of Pharmaceutical Sciences, Vol. 85, Issue 2, Pages 501-510, 2023.
  • [16] Yusuf, A., Abdullahi, M., Haruna, A., Musa, A., Abdullahi, M., Ibrahim, Z., Halilu, M., Odiba, O., "Phytochemical and antimicrobial evaluations of the methanol stem bark extract of Neocarya macropylla", Journal of Chemical and Pharmaceutical Research, Vol. 7, Issue 1, Pages 477-481, 2015.
  • [17] Hassan, L. G., Umar, K. J., Yusuf, A. J., Rabah, A. B., Umar, A.U., “Comparative Antimicrobial Activity of Securidaca longipedunculata (Fresen) Extracts on Selected Human Pathogens”, Saudi Journal of Medical and Pharmaceutical Sciences, Vol. 10, Issue 1, Pages 26-31, 2024.
  • [18] Chandrasekaran, M., Venkatesalu, V., "Antibacterial and antifungal activity of syzygium jambolanum seeds," Journal of ethnopharmacology, Vol. 91, Issue 1, Pages 105-108, 2004.

Bazı N-Sübstitüe Ftalimid Türevlerinin Antimikrobiyal Etkilerinin İncelenmesi

Year 2024, , 57 - 61, 27.10.2024
https://doi.org/10.5281/zenodo.13996463

Abstract

Bu çalışmada, bazı N-sübstitüe ftalimid türevlerinin (2, 3, 4a-c) antimikrobiyal etkileri Gram-negatif (jenerik Escherichia coli, Salmonella enterica Typhimurium, Citrobacter freundii, Klebsiella pneumoniae, şiga toksin üreten E. coli O157:H7 (STEC O157:H7)) ve Gram-pozitif bakteriler (Stapylococcus aureus, Listeria monocytogenes) üzerinde incelenmiştir. N-sübstitüe ftalimid türevlerinin antifungal etkileri ise maya (Candida albicans) ve küf (Aspergillus brasiliensis) üzerinde test edilmiştir. Antimikrobiyal analizlerde bakterilere karşı vankomisin-30 µg (VA-30), rifampisin-5 µg (RA-5) ve tetrasiklin-30 µg (TE-30), funguslara karşı ise karşı flukonazol-25 µg (FZ-25) pozitif kontrol grubu olarak kullanılmıştır. Genel olarak, N-sübstitüe ftalimid türevlerinin (2, 3, 4a-c) Gram-negatif, Gram-pozitif bakteriler, maya ve küf üzerinde önemli antimikrobiyal aktivitelere sahip olduğu gözlemlenmiştir. Yapısında dietilamin grubu ihtiva eden 4c bileşiği C. freundii ve L. monocytogenes üzerinde diğer ftalimid türevlerine ve kontrol bileşiklerine göre en iyi aktiviteyi göstermiştir. Diğer taraftan Br içeren 3 bileşiğinin, C. freundii hariç hem antibakteriyel hem de antifungal etkisi ile geniş spektrumlu antimikrobiyal özelliklere sahip olduğu görülmüştür. Sonuç olarak, N-sübstitüe ftalimid türevleri (2, 3, 4a-c) yeni ümit verici antimikrobiyal ajanlar olarak düşünülebilir.

Thanks

Yazarlar Muş Alparslan Üniversitesi’ne teşekkür eder.

References

  • [1] Kushwaha, N., Kaushik, D., "Recent advances and future prospects of phthalimide derivatives", Journal of Applied Pharmaceutical Science, Vol. 6, Issue 3, Pages 159-171, 2016.
  • [2] Khokra, S. L., Arora, K., Mehta, H., Aggarwal, A., Yadav, M., "Common methods to synthesize benzothiazole derivatives and their medicinal significance", International Journal of Pharmaceutical Sciences and Research, Vol. 2, Issue 6, Pages 1356-1378, 2011.
  • [3] Pawar, N. S., Patil, J. U., Suryawanshi, K. C., Chaudhary, S. R., Patil, P.B., "An improved microwave irradiation method for synthesis of some new N-alkyl and N-alkyloxy phthalimides", Der Pharma Chemica, Vol. 4, Issue 1, Pages 15-22, 2012.
  • [4] Bhat, M.A., Al-Omar, M.A., Siddiqui, N., "Synthesis, anticonvulsant and neurotoxicity of some novel 1, 3, 4-oxadiazole derivatives of phthalimide", Der Pharma Chemica, Vol. 2, Issue 2, Pages 1-10, 2010.
  • [5] Tan, A., Almaz, Z., "Synthesis, investigation of the cholinesterase inhibitory activities and in silico studies of some novel N-substituted phthalimide derivatives", Journal of the Iranian Chemical Society, Vol. 19, Issue 7, Pages 2833-2844, 2022. (and therein)
  • [6] Al-Qaisi, J.A., Alhussainy, T.M., Qinna, N.A., Matalka, K.Z., Al-Kaissi, E.N., Muhi-Eldeen, Z.A., "Synthesis and pharmacological evaluation of aminoacetylenic isoindoline-1,3-dione derivatives as anti-inflammatory agents", Arabian Journal of Chemistry, Vol. 7, Issue 6, Pages 1024-1030, 2014.
  • [7] Othman, I.M., Gad-Elkareem, M.A., El-Naggar, M., Nossier, E. S., Amr, A.E.G.E., "Novel phthalimide based analogues: Design, synthesis, biological evaluation, and molecular docking studies", Journal of enzyme inhibition and medicinal chemistry, Vol. 34, Issue 1, Pages 1259-1270, 2019.
  • [8] Bansal, R., Karthikeyan, C., Moorthy, N., Trivedi, P., "QSAR analysis of some phthalimide analogues based inhibitors of HIV-1 integrase", Arkivoc, Vol. 15, Issue xv, Pages 66-81, 2007.
  • [9] Patil, M., Rajput. S., “Synthesis and antimicrobial evaluation of some novel diazo derivative of cyclic Imides using diazotization coupling reaction”, Chemical science review and letters, Vol. 5, Issue 17, Pages 46-52, 2016.
  • [10] Kumari, S., Gupta, V, Singh, S. Gupta, Y., "Synthesis, “Characterization and antimicrobial activities of five and six member cyclic imides derivatives”, Research Journal of Science and Technology, Vol. 11, Issue 1, Pages 82-86, 2019.
  • [11] Stiz, D., Corrêa, R., Dauria, F., Simonetti, G., Cechinel-Filho, V., “Synthesis of cyclic imides (Methylphtalimides, carboxylic acid phtalimides and itaconimides) and evaluation of their antifungal potential”, Medicinal Chemistry, Vol. 12, Issue 7, Pages 647- 654, 2016.
  • [12] Chaudhari, P., Rajput, S., “One pot synthesis and antimicrobial evaluation of some novel bis-chalcones and pyrazoles from cyclic imides under microwave irradiation”, World Journal of Pharmaceutical Research, Vol. 5, Issue 8, Pages 1301-1313, 2016.
  • [13] Ahmed, W.S., Mahmood, A.A.R., Al-Bayati, R.I., “Synthesis and evaluation of antimicrobial activity of new imides and schiff bases derived from ethyl-4-amino benzoate”, Oriental Journal of Chemistry, Vol. 34, Issue 5, 2018.
  • [14] Baluja, S., Chanda, S., Chavda, K., “Synthesis, characterization and in vitro antimicrobial activity of cyclic imide: Isoindoline-1, 3-dione derivatives”, GSC Biological and Pharmaceutical Sciences, Vol. 10, Issue 1, Pages 046-058, 2020.
  • [15] Fekambaram, D., Santhy, K., "Phytochemical characterization and assessment of hygrophila auriculata (buch.-ham) leaves for antioxidant and antimicrobial activity", Indian Journal of Pharmaceutical Sciences, Vol. 85, Issue 2, Pages 501-510, 2023.
  • [16] Yusuf, A., Abdullahi, M., Haruna, A., Musa, A., Abdullahi, M., Ibrahim, Z., Halilu, M., Odiba, O., "Phytochemical and antimicrobial evaluations of the methanol stem bark extract of Neocarya macropylla", Journal of Chemical and Pharmaceutical Research, Vol. 7, Issue 1, Pages 477-481, 2015.
  • [17] Hassan, L. G., Umar, K. J., Yusuf, A. J., Rabah, A. B., Umar, A.U., “Comparative Antimicrobial Activity of Securidaca longipedunculata (Fresen) Extracts on Selected Human Pathogens”, Saudi Journal of Medical and Pharmaceutical Sciences, Vol. 10, Issue 1, Pages 26-31, 2024.
  • [18] Chandrasekaran, M., Venkatesalu, V., "Antibacterial and antifungal activity of syzygium jambolanum seeds," Journal of ethnopharmacology, Vol. 91, Issue 1, Pages 105-108, 2004.
There are 18 citations in total.

Details

Primary Language Turkish
Subjects Food Engineering
Journal Section Research Article
Authors

Sefa Işık 0000-0002-1480-7230

Ayşe Tan 0000-0003-2692-7923

Publication Date October 27, 2024
Submission Date July 31, 2024
Acceptance Date October 7, 2024
Published in Issue Year 2024

Cite

APA Işık, S., & Tan, A. (2024). Bazı N-Sübstitüe Ftalimid Türevlerinin Antimikrobiyal Etkilerinin İncelenmesi. Hendese Teknik Bilimler Ve Mühendislik Dergisi, 1(2), 57-61. https://doi.org/10.5281/zenodo.13996463