Abstract
Oxadiazole derivatives have been extensively studied for their specific and potent pharmacological property. Oxadiazole ring is susceptible to undergo electrophilic and nucleophilic substitution which makes it an interesting candidate to synthesize new derivatives with potential biological activity. Keeping in view their significance, the present work highlights the synthesis of a series of new oxadiazole derivatives from recycled poly(ethylene terephthalate) PET by chemical route. The aminolyzed product of PET i.e. terephthalic dihydrazide is being used for preparation of oxadiazole derivatives. The characterization of the synthesized product was done via FTIR, UV–visible, 1H-NMR and thermal analysis. The compounds showed potential antimicrobial activity against Candida albicans, Rhizopus, Bacillus cereus and Escherichia coli. Further, molecular docking of the compounds were studied for target proteins Sterol 14α-demethylase, TREX1, and Glucosamine-6-phosphate synthase. The binding energy between the target protein and ligand is calculated and interaction between the two is discussed. The antimicrobial activity carried out for the derivatives were in close correlation with in silico docking study performed.
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Gupta RR, Kumar M, Gupta V (2005) Heterocyclic chemistry: five members heterocyclic. Springer, Berlin, p 203
Palekar VS, DamLe AJ, Shukla SR (2009) Eur J Med Chem 4:5112
Akhtar T, Hameed S, Al-Masoudi NA, Loddo R, La Colla P (2008) Acta Pharm 58:135
Bakht MA, Yar MS, Abdel-Hamid SG, Al Qasoumi SI, Samad A (2010) Eur J Med Chem 45:5862
Sangshetti JN, Chabukswar AR, Shinde DB (2011) Bioorg Med Chem Lett 21:444
Ahsan MJ, Samy GJ, Jain CB, Dutt KR, Khalilullah H, Nomani MS (2012) Bioorg Med Chem Lett 21:969
de Oliveira CS, Lira BF, Barbosa-Filho JM, Lorenzo JG, de Athayde-Filho PF (2012) Molecules 17:10192
Li Y, Zhu H, Chen K K, Liu R, Khallaf A, Zhang XN, Ni J (2013) Org Biomol Chem 11:3979
Ramaprasad GC, Kalluraya B, Kumar S, Mallaya S (2013) Med Chem Res 22:5381
Rehman A, Fatima N, Abbas N, Abbasi MA, Khan KM, Ashraf M, Ahmad I, Ejaz SA (2013) Pak J Pharm Sci 26:345
Shukla SR, Harad AM (2006) Polym Degrad Stab 91:1850
Hoang CN, Dang YH (2013) Polym Degrad Stab 98:697
Popoola VA (1988) J Appl Polym Sci 36:1677
Collin G, Cooney JD, Carlsson DJ, Wiles DM (1981) J Appl Polym Sci 26:509
Soni RK, Singh S, Dutt K (2009) J Appl Polym Sci 115:3074
Agrawal R, Tarannum N, Soni RK (2016) Der Pharma Chem 8:137
Chmara H, Andruszkiewicz R, Borowski E (1984) Biochem Biophys Res Commun 120:865
Milewski S, Chmara H, Andruszkiewicz R, Borowski E, Zaremba M, Borowski J (1988) Drugs Exp Clin Res 14:461
Vanden Bossche H, Koymans L (1998) Mycoses 41:32
Sheehan DJ, Hitchcock CA, Sibley CM (1999) Clin Microbiol Rev 12:40
Yoshida Y, Aoyama Y, Noshiro M, Gotoh O (2000) Biochem Biophys Res Commun 273:799
Lindahl T, Gally JA, Edelman GM (1969) J Biol Chem 244:5014
Perrino FW, Mazur DJ, Ward H, Harvey S (1999) Cell Biochem Biophys 30:331
Perrino FW, Miller H, Ealey KA (1994) J Biol Chem 269:16357
Santos-Pereira JM, Herrero AB, Garcia-Rubio M, Antonio M, Sergio M, Aguilera A (2013) Genes Dev 27:2445
Crow YJ, Hayward BE, Parmar R, Robins P, Leitch A, Ali M, Black DN, van Bokhoven H, Brunner HG, Hamel BC, Corry PC, Cowan FM, Frints SG, Klepper J, Livingston JH, Lynch SA, Massey RF, Meritet JF, Michaud JL, Ponsot G, Voit T, Lebon P, Bonthron DT, Jackson AP, Barnes DE, Lindahl T (2006) Nat Genet 38:917
Richards A, van den Maagdenberg AM, Jen JC, Kavanagh D, Bertram P, Spitzer D, Liszewski MK, Barilla-Labarca ML, Terwindt GM, Kasai Y, McLellan M, Grand MG, Vanmolkot KR, de Vries B, Wan J, Kane MJ, Mamsa H, Schäfer R, Stam AH, Haan J, de Jong PT, Storimans CW, van Schooneveld MJ, Oosterhuis JA, Gschwendter A, Dichgans M, Kotschet KE, Hodgkinson S, Hardy TA, Delatycki MB, Hajj-Ali RA, Kothari PH, Nelson SF, Frants RR, Baloh RW, Ferrari MD, Atkinson JP (2007) Nat Genet 39:1068
Lee-Kirsch MA, Chowdhury D, Harvey S, Gong M, Senenko L, Engel K, Pfeiffer C, Hollis T, Gahr M, Perrino FW, Lieberman J, Hubner N (2007) J Mol Med 85:531
Lee-Kirsch MA, Gong M, Chowdhury D, Senenko L, Engel K, Lee YA, de Silva U, Bailey SL, Witte T, Vyse TJ, Kere J, Pfeiffer C, Harvey S, Wong A, Koskenmies S, Hummel O, Rohde K, Schmidt RE, Dominiczak AF, Gahr M, Hollis T, Perrino FW, Lieberman J, Hübner N (2007) Nat Genet 39:1065
Rice G, Newman WG, Dean J, Patrick T, Parmar R, Flintoff K, Robins P, Harvey S, Hollis T, O’Hara A, Herrick AL, Bowden AP, Perrino FW, Lindahl T, Barnes DE, Crow YJ (2007) Am J Hum Genet 80:811
Tomi IHR, Al-Daraji AHR, Al-Qaysi RRT, Hassson MM, Al-Dulaimy KHD (2013) J Saudi Chem Soc. 10.1016/j.jscs.2013.03.004
Raman N, Kulandaisamy A, Sanmugasundaram A, Subramanian J (2001) Trans Met Chem 26:131
Bochevarov AD, Harde E, Hughes TF, Greenwood JR, Braden DA, Philipp DM, Rinaldo D, Halls MD, Zhang J, Friesner RA (2013) Int J Quantum Chem 113:2110
Schrödinger Release 2015-3 (2015) LigPrep, version 3.5. Schrödinger, LLC, New York
Sastry GM, Adzhigirey M, Day T, Annabhimoju R, Sherman W (2013) J Comput Aid Mol Des 27:221
Friesner RA, Banks JL, Murphy RB, Halgren TA, Klicic JJ, Mainz DT, Repasky MP, Knoll EH, Shaw DE, Shelley M, Perry JK, Francis P, Shenkin PS (2004) J Med Chem 47:1739
Acknowledgements
The authors would like to acknowledge SAIF, Cochin, India for carrying out the spectral studies. RA1 would like to acknowledge UGC (Reference No. 13-844) for granting DSK fellowship. MC thank NIPER, Department of Pharmaceuticals, Ministry of Chemicals and Fertilizers for providing necessary facility.
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Agrawal, R., Tarannum, N., Chourasia, M. et al. Chemical Degradation of Poly(ethylene terephthalate) for Potential Antimicrobial Activity Evaluation and Molecular Docking Study. J Polym Environ 26, 819–829 (2018). https://doi.org/10.1007/s10924-017-0987-4
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DOI: https://doi.org/10.1007/s10924-017-0987-4