دورية أكاديمية

Antioxidant and Antimicrobial Potential of 1,8-Naphthyridine Based Scaffolds: Design, Synthesis and in Silico Simulation Studies within Topoisomerase II.

التفاصيل البيبلوغرافية
العنوان: Antioxidant and Antimicrobial Potential of 1,8-Naphthyridine Based Scaffolds: Design, Synthesis and in Silico Simulation Studies within Topoisomerase II.
المؤلفون: Elkanzi NAA; Chemistry Department, college of Science, Jouf University, 2014, Sakaka, Saudi Arabia., Hrichi H; Chemistry Department, college of Science, Jouf University, 2014, Sakaka, Saudi Arabia., Muqbil Alsirhani A; Chemistry Department, college of Science, Jouf University, 2014, Sakaka, Saudi Arabia., Bakr RB; Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Beni-Suef University, 62514, Beni-Suef, Egypt.
المصدر: Chemistry & biodiversity [Chem Biodivers] 2024 Jun; Vol. 21 (6), pp. e202301746. Date of Electronic Publication: 2024 May 15.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Verlag Helvetica Chimica Acta Country of Publication: Switzerland NLM ID: 101197449 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1612-1880 (Electronic) Linking ISSN: 16121872 NLM ISO Abbreviation: Chem Biodivers Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Zürich, Switzerland : Hoboken, NJ : Verlag Helvetica Chimica Acta ; Distributed in the USA by Wiley, c2004-
مواضيع طبية MeSH: Anti-Bacterial Agents*/pharmacology , Anti-Bacterial Agents*/chemical synthesis , Anti-Bacterial Agents*/chemistry , Antifungal Agents*/pharmacology , Antifungal Agents*/chemical synthesis , Antifungal Agents*/chemistry , Antioxidants*/pharmacology , Antioxidants*/chemical synthesis , Antioxidants*/chemistry , DNA Topoisomerases, Type II*/metabolism , Drug Design* , Fungi*/drug effects , Microbial Sensitivity Tests* , Naphthyridines*/pharmacology , Naphthyridines*/chemistry , Naphthyridines*/chemical synthesis, Bacteria/drug effects ; beta-Lactams/chemical synthesis ; beta-Lactams/chemistry ; beta-Lactams/pharmacology ; Biphenyl Compounds/antagonists & inhibitors ; Molecular Docking Simulation ; Molecular Structure ; Picrates/antagonists & inhibitors ; Structure-Activity Relationship ; Topoisomerase II Inhibitors/pharmacology ; Topoisomerase II Inhibitors/chemistry ; Topoisomerase II Inhibitors/chemical synthesis ; Spiro Compounds/chemical synthesis ; Spiro Compounds/chemistry ; Spiro Compounds/pharmacology
مستخلص: A series of spiro β-Lactams (4 a-c, 7 a-c) and thiazolidinones (5 a-c, 8 a-c) possessing 1,8-naphthyridine moiety were synthesized in this study. The structure of the newly synthesized compounds has been confirmed by IR, 1 H-NMR, 13 C NMR, mass spectra, and elemental analysis. The synthesized compounds were tested in vitro for their antibacterial and antifungal activity against various strains. The antimicrobial data showed that most of the compounds displayed good efficacy against both bacteria and fungi. The structure-activity relationship (SAR) studies suggested that the presence of electron-withdrawing chloro (3 b, 4 b, and 5 b) and nitro groups (7 b, 8 b) at the para position of the phenyl ring improved the antimicrobial activity of the compounds. The free radical scavenging assay showed that all the synthesized compounds exhibited significant antioxidant activity on DPPH. Compounds 8 b (IC 50 =17.68±0.76 μg/mL) and 4 c (IC 50 =18.53±0.52 μg/mL) showed the highest antioxidant activity compared to ascorbic acid (IC 50 =15.16±0.43 μg/mL). Molecular docking studies were also conducted to support the antimicrobial and SAR results.
(© 2024 Wiley-VHCA AG, Zurich, Switzerland.)
References: P. Rani, D. K. Pal, R. R. Hegde, S. R. Hashim, Hem. Ind. 2015, 69, 405–415.
M. A. Abdelgawad, A. Musa, A. H. Almalki, S. I. Alzarea, E. M. Mostafa, M. M. Hegazy, et al., Drug Des. Dev. Ther. 2021, 15, 2325.
R. A. Shinde, V. A. Adole, R. D. Amrutkar, S. R. Tambe, B. S. Jagdale, Polycyclic Aromat. Compd. 2023, 1–23.
R. A. Shinde, V. A. Adole, B. S. Jagdale, J. Mol. Struct. 2024, 1300, 137096.
R. H. Waghchaure, V. A. Adole, J. Mol. Struct. 2024, 1296, 136724.
K. B. Gangurde, R. A. More, V. A. Adole, D. S. Ghotekar, J. Mol. Struct. 2024, 1299, 136760.
S. S. Choudhury, S. Jena, D. K. Sahoo, S. Shekh, R. K. Kar, A. Dhakad, et al., ACS Omega 2021, 6, 19304–19313.
M. A. Alanazi, W. A. Arafa, I. O. Althobaiti, H. A. Altaleb, R. B. Bakr, N. A. Elkanzi, ACS Omega 2022, 7, 27674–27689.
N. A. Elkanzi, I. H. El Azab, R. B. Bakr, Polycyclic Aromat. Compd. 2022, 42(9), 6760–6779.
M. T. Riaz, M. Yaqub, S. Javed, D. Hussain, M. N. Ashiq, Z. Shafiq, J. Taibah Univ. Sci. 2021, 15, 559–566.
K. Vennila, B. Selvakumar, V. Satish, D. Sunny, S. Madhuri, K. Elango, Med. Chem. Res. 2021, 30, 133–141.
N. Kaur, Synth. Commun. 2015, 45, 35–69.
M. Andrews, R. H. Laye, S. J. Pope, Transition Met. Chem. 2009, 34, 493–497.
S. Abu-Melha, Acta Chim. Slov. 2017, 64, 919–930.
A. A. Mohammed, G. A. Suaifan, M. B. Shehadeh, P. N. Okechukwu, Drug Dev. Res. 2019, 80, 179–186.
T. R. Makhanya, R. M. Gengan, A. Ata, Synth. Commun. 2019, 49, 823–835.
B. Sakram, B. Sonyanaik, K. Ashok, S. Rambabu, D. Ravi, A. Kurumanna, et al., Res. Chem. Intermed. 2017, 43, 1881–1892.
N. A. A. Elkanzi, A. A. Ghoneim, R. B. Bakr, PharmaChem 2019, 11, 6–13.
V. K. Gurjar, D. Pal, RSC Adv. 2020, 10, 13907–13921.
V. Kumar, M. Jaggi, A. T. Singh, A. Madaan, V. Sanna, P. Singh, et al., Eur. J. Med. Chem. 2009, 44, 3356–3362.
A. Madaan, V. Kumar, R. Verma, A. T. Singh, S. Jain, M. Jaggi, Int. Immunopharmacol. 2013, 15, 606–613.
A. N. Al-romaizan, T. S. Jaber, N. S. Ahmed, Open Chemistry 2019, 17, 943–954.
L. Fu, X. Feng, J.-J. Wang, Z. Xun, J.-D. Hu, J.-J. Zhang, et al., ACS Comb. Sci. 2015, 17, 24–31.
A. K. Elansary, A. A. Moneer, H. H. Kadry, E. M. Gedawy, J. Chem. Res. 2014, 38, 147–153.
E. P. Garvey, B. A. Johns, M. J. Gartland, S. A. Foster, W. H. Miller, R. G. Ferris, et al., Antimicrob. Agents Chemother. 2008, 52, 901–908.
I. P. Singh, S. Kumar, S. Gupta, Med. Chem. 2017, 13, 430–438.
J. A. Al jamal, M. Badawneh, Arch. Pharm. 2003, 336, 285–292.
B. K. Gautam, A. Jindal, A. K. Dhar, R. Mahesh, Pharmacol. Biochem. Behav. 2013, 109, 91–97.
R. Mahesh, A. K. Dhar, A. Jindal, S. Bhatt, Can. J. Physiol. Pharmacol. 2013, 91, 848–854.
J. D. Gohil, H. B. Patel, M. P. Patel, RSC Adv. 2016, 6, 74726–74733.
B. Sakram, K. Ashok, S. Rambabu, B. Sonyanaik, D. Ravi, Russ. J. Gen. Chem. 2017, 87, 1794–1799.
A. B. Petersen, M. H. Rønnest, T. O. Larsen, M. H. Clausen, Chem. Rev. 2014, 114, 12088–12107.
F. Golmohammadi, S. Balalaie, V. Fathi Vavsari, M. U. Anwar, A. Al-Harrasi, J. Org. Chem. 2020, 85, 13141–13152.
Y.-J. Zheng, C. M. Tice, Expert Opin. Drug Discovery 2016, 11, 831–834.
R. Rios, Chem. Soc. Rev. 2012, 41, 1060–1074.
A. Ding, M. Meazza, H. Guo, J. W. Yang, R. Rios, Chem. Soc. Rev. 2018, 47, 5946–5996.
H. Abdellaoui, J. Xu, Tetrahedron 2014, 70, 4323–4330.
J. W. Skiles, D. McNeil, Tetrahedron Lett. 1990, 31, 7277–7280.
A. Verma, S. K. Saraf, Eur. J. Med. Chem. 2008, 43, 897–905.
M. Djukic, M. Fesatidou, I. Xenikakis, A. Geronikaki, V. T. Angelova, V. Savic, et al., Chem.-Biol. Interact. 2018, 286, 119–131.
R. B. Bakr, N. A. Elkanzi, J. Heterocycl. Chem. 2020, 57, 2977–2989.
H. Zhang, J. Zhang, W. Qu, S. Xie, L. Huang, D. Chen, et al., Front. Chem. 2020, 8, 598.
A. Türe, M. Ergül, M. Ergül, A. Altun, İ. Küçükgüzel, Mol. Diversity 2021, 25, 1025–1050.
S. B. Bari, S. D. Firake, Anti-Inflammatory Anti-Allergy Agents Med. Chem. 2016, 15, 44–53.
N. Saini, A. Sharma, V. K. Thakur, C. Makatsoris, A. Dandia, M. Bhagat, et al., Curr. Res. Green Sustain. Chem. 2020, 3, 100021.
K. D. Asgaonkar, S. M. Patil, T. S. Chitre, V. N. Ghegade, S. R. Jadhav, S. S. Sande, et al., Curr. Comput.-Aided Drug Des. 2019, 15, 252–258.
V. Ravichandran, A. Jain, K. S. Kumar, H. Rajak, R. K. Agrawal, Chem. Biol. Drug Des. 2011, 78, 464–470.
N. A. A. Elkanzi, H. A. A. E.-M. Yosef, N. M. M. Mohamed, Eur. J. Chem. 2013, 4, 195–202.
R. B. Bakr, N. A. Elkanzi, Lett. Drug Des. Discovery 2022, 19, 675–690.
N. A. Elkanzi, H. Hrichi, R. B. Bakr, O. Hendawy, M. M. Alruwaili, E. D. Alruwaili, et al., J. Iran. Chem. Soc. 2021, 18, 977–991.
N. A. Elkanzi, R. B. Bakr, Lett. Drug Des. Discovery 2020, 17, 1538–1551.
H. Hrichi, E. N. A. Ahmed, B. R. Badawy, Chem. J. Mold. 2020, 15, 86–94.
N. A. Elkanzi, H. Hrichi, R. A. Alolayan, W. Derafa, F. M. Zahou, R. B. Bakr, ACS Omega 2022, 7, 27769–27786.
M. A. Abdelgawad, M. M. Al-Sanea, A. Musa, M. Elmowafy, A. K. El-Damasy, A. A. Azouz, et al., J. Inflamm. Res. 2022, 15, 451.
M. A. Abdelgawad, A. Musa, A. H. Almalki, S. I. Alzarea, E. M. Mostafa, M. M. Hegazy, et al., Drug Des. Dev. Ther. 2021, 15, 2325–2337.
R. B. Bakr, A. Mehany, Molbank 2016, 2016, M915.
B. B. Rania, A. Nadia, A. G. Amira, M. Shaima, Heterocycles 2018, 96, 1941–1957.
N. A. A. Elkanzi, A. A. Ghoneim, R. B. Bakr, PharmaChem 2019, 11, 6–13.
B. Mathew, D. G. Parambi, M. Singh, O. M. Hendawy, M. M. Al-Sanea, R. B. Bakr, Protopine. Naturally Occurring Chemicals Against Alzheimer's Disease: Elsevier; 2021. p. 167–174.
M. E. Shaker, H. A. Goma, I. Alsalahat, N. A. Elkanzi, A. A. Azouz, M. S. Abdel-Bakky, et al., J. Biomol. Struct. Dyn. 2023, 1–14.
N. A. Elkanzi, A. Farag, N. Roushdy, A. Mansour, Optik 2020, 216, 164882.
N. F. Santos-Sánchez, R. Salas-Coronado, C. Villanueva-Cañongo, B. Hernández-Carlos, Antioxidants 2019, 10, 1–29.
I. R. Ilyasov, V. L. Beloborodov, I. A. Selivanova, R. P. Terekhov, Int. J. Mol. Sci. 2020, 21, 1131.
S. Santosh Kumar, K. Priyadarsini, K. Sainis, Redox Rep. 2002, 7, 35–40.
K. N. Mohana, C. B. P. Kumar, Int. Sch. Res. Notices 2013, 2013.
E. Bendary, R. Francis, H. Ali, M. Sarwat, S. El Hady, Ann. Agric. Sci. 2013, 58, 173–181.
S. A. Komykhov, K. S. Ostras, A. R. Kostanyan, S. M. Desenko, V. D. Orlov, H. Meier, J. Heterocycl. Chem. 2005, 42, 1111–1116.
V. Panteleon, I. K. Kostakis, P. Marakos, N. Pouli, I. Andreadou, Bioorg. Med. Chem. Lett. 2008, 18, 5781–5784.
A. Aouf, S. Bouaouina, M. A. Abdelgawad, M. A. Abourehab, A. Farouk, Antibiotics 2022, 11, 1317.
معلومات مُعتمدة: DGSSR-2023-02-02073 Deanship of Graduate Studies and Scientific Research at Jouf University
فهرسة مساهمة: Keywords: 1,8-naphthyridine; antimicrobial; antioxidant; spiro β-Lactam; thiazolidinone
المشرفين على المادة: DFD3H4VGDH (1,1-diphenyl-2-picrylhydrazyl)
0 (Anti-Bacterial Agents)
0 (Antifungal Agents)
0 (Antioxidants)
0 (beta-Lactams)
0 (Biphenyl Compounds)
EC 5.99.1.3 (DNA Topoisomerases, Type II)
0 (Naphthyridines)
0 (Picrates)
0 (Topoisomerase II Inhibitors)
0 (Spiro Compounds)
تواريخ الأحداث: Date Created: 20240309 Date Completed: 20240618 Latest Revision: 20240621
رمز التحديث: 20240621
DOI: 10.1002/cbdv.202301746
PMID: 38459958
قاعدة البيانات: MEDLINE
الوصف
تدمد:1612-1880
DOI:10.1002/cbdv.202301746