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Tytuł artykułu

Synthesis, characterization, and molecular modeling of novel 1,3,4-oxadiazole derivatives of mefenamic acid

Treść / Zawartość
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A novel series of 1,3,4-oxadiazole derivatives of mefenamic acid was obtained by reacting hydrazones of mefenamic acid with anhydrous acetic anhydride. The mefenamic hydrazones were obtained by reacting different substituted aldehydes with mefenamic acid hydrazide. All the compounds were characterized by spectral data and elemental analysis. Molecular docking studies of all the compounds were performed against COX-1/COX-2 enzymes. Compound 4 and compound 10 were found to have the highest potential to bind with COX-1 while compound 3, compound 6, and compound 10 were found to have the highest potential to bind with COX-2 enzyme.
Rocznik
Strony
102--112
Opis fizyczny
Bibliogr. 33 poz., rys., tab., wz.
Twórcy
  • Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University Riyadh, Saudi Arabia
  • Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University Riyadh, Saudi Arabia
  • Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University Riyadh, Saudi Arabia
  • Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University Riyadh, Saudi Arabia
Bibliografia
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  • 6. Somani, R.R. & Bhanushali, U.V. (2011). Synthesis and evaluation of the anti-inflammatory, analgesic and ulcerogenic potential of NSAIDs bearing 1, 3, 4-oxadiazole scaffold. Indian J. Pharm. Sci. 73, 634–640. DOI: 10.4103/0250-474X.100237.
  • 7. Salih, N., Salimon, J., Hameed, A. & Yousif, E. (2011). Synthesis, characterization and antimicrobial evaluation of some 1,3,4-oxadiazole derivatives. Int. J. Pharm. Tech. Res. 3, 1097–1102.
  • 8. Malhotra, M., Sanduja, M., Samad, A. & Deep, A. (2012). New oxadiazole derivatives of isonicotinohydrazide in the search for antimicrobial agents: synthesis and in vitro evaluation. J. Serb. Chem. Soc. 77, 9–16. DOI: 10.2298/JSC110123155M.
  • 9. Singh, I. & Kumar, A. (2015). Synthesis and antibacterial activity of 2-(substituted phenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazoles. Chem. Sci. Trans. 4, 133–136. DOI: 10.7598/cst2015.941.
  • 10. Sahu, V.K.R., Singh, A.K. & Yadav, D. (20111). Review article on 1,3,4-oxadiazole derivatives and its pharmacological activities. Int. J. Chem. Tech. Res. 3, 1362–1372.
  • 11. Husain, A. & Ajmal, M. (2009). Synthesis of novel 1, 3, 4-oxadiazole derivatives and their biological properties. Acta Pharm. 59, 223–233. DOI: 10.2478/v10007-009-0011-1.
  • 12. Singh, A.K., Lohani, M. & Parthsarthy, R. (2013). Synthesis, characterization and anti-inflammatory activity of some 1,3,4-oxadiazole derivatives. Iran J. Pharm. Res. 12, 319–323.
  • 13. Joshi, S.D., Vagdevi, H.M., Vaidya, V.P. & Gadagina-math, G.S. (2008). Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: A novel class of potential antibacterial and antitubercular agents. Eur. J. Med. Chem. 43, 1989–1996. DOI: 10.1016/j.ejmech.2007.11.016.
  • 14. Redhu, S. & Kharb, R. (2013). Recent updates on chemistry and pharmacological aspects of 1, 3, 4-oxadiazole scaffold. Int. J. Pharm. Innovation. 3, 93–110.
  • 15. de Oliveira, C.S., Lira, B.F., Barbosa-Filho, J.M., Lorenzo, J.G. & de Athayde-Filho, P.F. (2012). Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: a review of the literature from 2000-2012. Molecules.17, 10192–10231. DOI: 10.3390/molecules170910192.
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  • 17. Azzawi, A.M.A. & Al-Obiadi, K.K.H. (2016). Synthesis and antimicrobial screening new bis Shiff bases and their acetyl oxadiazole azetidinone derivatives from pyromelliticdiimide. Int. J. Res. Pharm. Chem. 6, 1–8.
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  • 19. Singh, R. & Chouhan, A. (2014). Various approaches for synthesis of 1, 3, 4-Oxadiazole derivatives and their pharmacological activity. World J. Pharm. Pharm. Sci. 3, 1474–1505.
  • 20. Zheng, X., Li, Z., Wang, Y., Chen, W., Huang, Q., Liu, C. & Song, G. (2003). Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles. J. Fluorine Chem. 123, 163–169. DOI: 10.1016/S0022-1139(03)00168-4.
  • 21. Kumar, R., Yar, M.S., Rai, A.K. & Chaturvedi, S. (2013). Synthesis and biological evaluation of some novel 1, 3, 4-oxadiazoles derived from bi phenyl 4- carboxylic acid. Der Pharm. Lett. 5, 366–370.
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  • 24. Khalaf, H.S., Naglah, A.M., Al-Omar, M.A., Moustafa, G.O., Awad, H.M. & Bakheit, A.H. (2020). Synthesis, docking, computational studies, and antimicrobial evaluations of new dipeptide derivatives based on nicotinoylglycylglycine hydrazide. Molecules, 25, 3589. DOI: 10.3390/molecules25163589.
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  • 27. Dewar, M.J.S., Zoebisch, E.G., Healy, E.F. & Stewart J.J.P. (1985). Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902–3909. DOI: 10.1021/ja00299a024.
  • 28. Chandrasekhar, T., Kumar, L.V., Reddy, A.B., Naik, J.P. & Swamy, G.N. (2012). Synthesis and biological evaluation of some new aryl acid N0 – (1Hindazole-3-carbonyl)-hydrazide derivatives. J. Chem. Pharm. Res. 4, 2795–2802.
  • 29. Onnis, V., Cocco, M.T., Fadda, R. & Congiu, C. (2009). Synthesis and evaluation of anticancer activity of 2-arylamino-6-trifluoromethyl-3-(hydrazonocarbonyl)pyridines. Bioorg. Med. Chem. 17, 6158–6165. DOI: 10.1016/j.bmc.2009.07.066.
  • 30. Reddy, L.V., Suman, A., Beevi, S.S., Mangamoori, L.N., Mukkanti, K. & Pal, S. (2010). Design and synthesis of 1-aroyl-2-ylidene hydrazines under conventional and microwave irradiation conditions and their cytotoxic activities. J. Braz. Chem. Soc. 21, 98–104. DOI: 10.1590/S0103-50532010000100015.
  • 31. Bhat, M.A., Al-Omar, M.A., Alsaif, N.A., Almehizia, A.A., Naglah, A.M., Razak, S., Khan, A.A. & Ashraf, N.M. (2020). Novel sulindac derivatives: synthesis, characterisation, evaluation of antioxidant, analgesic, anti-inflammatory, ulcerogenic and COX-2 inhibition activity. J. Enz. Inhib. Med. Chem. 35, 921–934. DOI: 10.1080/14756366.2020.
  • 32. Bhat, M.A. (2014). Synthesis and anti-mycobacterial activity of new 4-thiazolidinone and 1,3,4-oxadiazole derivatives of isoniazid. Acta Pol. Pharm. 71, 763–770.
  • 33. Bhat, M.A., Khan, S.A. & Siddiqui, N. (2005). Synthesis and antibacterial activity of coumarin incorporated 1,3,4-oxadiazoles. Indian J. Het. Chem. 14, 271–272.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-76d143e1-4edf-47a0-a84b-cbf56e1a9859
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