Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Antitumor and Antioxidant Activities of the New Synthesized Azomethine Derivatives: Experimental and Theoretical Investigations

Author(s): Siyamak Shahab*, Masoome Sheikhi, Liudmila Filippovich, Evgenij Dikusar, Radwan Alnajjar, Mikhail Atroshko and Marina Drachilovskaya

Volume 18, Issue 1, 2021

Published on: 19 March, 2020

Page: [22 - 40] Pages: 19

DOI: 10.2174/1570178617666200319121649

Price: $65

Abstract

In this study, the antioxidant property of eight new azomethine derivatives underwent theoretical and experimental investigations. Azomethines have antioxidant activity. This is the first time the molecular structures and antioxidant property of these derivatives have been studied. The molecular structures were optimized using Density functional theory (DFT). The Bond Dissociation Enthalpy (BDE), Mulliken Charges, NBO analysis, Ionization Potential (IP), Electron Affinities (EA), HOMO and LUMO energies, Hardness (η), Softness (S), Electronegativity (μ), Electrophilic Index (ω), Electron Donating Power (ω-), Electron Accepting Power (ω+), and Energy Gap (Eg) were calculated in order to deduce scavenging action of the eight new synthesized azomethines (DIA-3,4,5,6,7,8,9,10). Spin density calculations and NBO analysis were also carried out to understand the antioxidant activity mechanism. These molecules have high antioxidant potential due to the planarity and formation of intramolecular hydrogen bonds. Experimental investigations establish high antioxidant and antitumor activities of the synthesized azomethine derivatives.

Keywords: Azomethine, antioxidant, antitumor, DFT, NBO, energy gap.

« Previous Next »
Graphical Abstract

[1]
Bolduc, A.; Dufresne, S.; Skene, W.G. J. Mater. Chem., 2012, 22, 5053-5064.
[http://dx.doi.org/10.1039/c2jm14248a]
[2]
Shahab, S.; Sheikhi, M.; Filippovich, L.; Khaleghian, M.; Dikusar, E.; Yahyaei, H.; Yousefzadeh Borzehandani, M. Silicon, 2018, 10, 2361-2385.
[http://dx.doi.org/10.1007/s12633-018-9773-8]
[3]
Iwan, A.; Schab-Balcerzak, E.; Grucela-Zajac, M.; Skorka, L. J. Mol. Struct., 2014, 1058, 130-135.
[http://dx.doi.org/10.1016/j.molstruc.2013.10.067]
[4]
Shahab, S.; Kumar, R.; Darroudi, M.; Borzehandani, M.Y. J. Mol. Struct., 2015, 1083, 198-203.
[http://dx.doi.org/10.1016/j.molstruc.2014.11.064]
[5]
Iwan, A.; Palewicz, M.; Krompiec, M.; Grucela-Zajac, M.; Schab-Balcerzak, E.; Sikora, A. Mol. Biomol. Spectrosc., 2012, 97, 546-555.
[http://dx.doi.org/10.1016/j.saa.2012.06.054]
[6]
Nowak, E.M.; Sanetra, J.; Grucela, M.; Schab-Balcerzak, E. Mater. Lett., 2015, 157, 93-98.
[http://dx.doi.org/10.1016/j.matlet.2015.05.122]
[7]
Shahab, S.; Sheikhi, M.; Filippovich, L.; Dikusar, E.; Yahyaei, H.; Kumar, R.; Khaleghian, M. J. Mol. Struct., 2018, 1157, 536-550.
[http://dx.doi.org/10.1016/j.molstruc.2017.12.094]
[8]
Sheikhi, M.; Shahab, S.; Filippovich, L.; Yahyaei, H.; Dikusar, E.; Khaleghian, M. J. Mol. Struct., 2018, 1152, 368-385.
[http://dx.doi.org/10.1016/j.molstruc.2017.09.108]
[9]
Shahab, S.; Filippovich, L.; Almodarresiyeh, H.A.; Sheikhi, M.; Kumar, R. J. Struct. Chem., 2018, 37, 186-197.
[10]
Almodarresiyeh, H.A.; Shahab, S.N.; Filippovich, L.N.; Ariko, N.G.; Lugovsky, A.P.; Agabekov, V.E. RSC Advances, 2016, 6, 42062-42068.
[http://dx.doi.org/10.1039/C6RA03548E]
[11]
Nowak, E.M.; Sanetra, J.; Grucela, M.; Schab-Balcerzak, E. Mater. Lett., 2015, 157, 93-98.
[http://dx.doi.org/10.1016/j.matlet.2015.05.122]
[12]
Geronikaki, A.; Vicini, P.; Incerti, M.; Hadjipavlou-Litina, D. Arzneimittelforschung, 2004, 54(9), 530-537.
[PMID: 15500199]
[13]
Tabassum, S.; Amir, S.; Arjmand, F.; Pettinari, C.; Marchetti, F.; Masciocchi, N.; Lupidi, G.; Pettinari, R. Eur. J. Med. Chem., 2013, 60, 216-232.
[http://dx.doi.org/10.1016/j.ejmech.2012.08.019 ] [PMID: 23291123]
[14]
da Silva, C.M.; da Silva, D.L.; Modolo, L.V.; Alves, R.B.; de Resende, M.A.; Martins, C.V.B.; Fatima, A. J. Adv. Res., 2011, 2, 1-8.
[http://dx.doi.org/10.1016/j.jare.2010.05.004]
[15]
Sridevi, C.; Neeraj Kumar, F.; Shivkanya, F.; Sundram, K.; Ravichandran, V.; Appala Raju, N.; Lim Jun, Y. Trop. J. Pharm. Res., 2016, 15, 821-826.
[16]
Sridevi, C.H.; Balaji, K.; Naidu, A.E-J. Chem, 2011, 8, 924-930.
[http://dx.doi.org/10.1155/2011/584817]
[17]
Parr, P.G.; Yang, W. J. Am. Chem. Soc., 1984, 106, 4049-4050.
[http://dx.doi.org/10.1021/ja00326a036]
[18]
Shahab, S.; Filippovich, L.; Sheikhi, M.; Yahyaei, H.; Aharodnikova, M.; Kumar, R.; Khaleghian, M. J. Mater. Synth. Process., 2017, 5, 17-23.
[19]
Shahab, S.; Filippovich, L.; Sheikhi, M.; Kumar, R.; Dikusar, E.; Yahyaei, H.; Muravsky, A. J. Mol. Struct., 2017, 1141, 703-709.
[http://dx.doi.org/10.1016/j.molstruc.2017.04.014]
[20]
Shahab, S.; Sheikhi, M.; Filippovich, L.; Dikusar Anatol’evich, E.; Yahyaei, H. J. Mol. Struct., 2017, 1137, 335-348.
[http://dx.doi.org/10.1016/j.molstruc.2017.02.056]
[21]
Magomedova, E.F.; Pinyaskin, V.V.; Aminova, A. Pharm. Chem. J., 2007, 41, 474-475.
[http://dx.doi.org/10.1007/s11094-007-0104-4]
[22]
Shahab, S.; Sheikhi, M.; Filippovich, L.; Dikusar, E.; Pazniak, A.; Rouhani, M.; Kumar, R. Curr. Mol. Med., 2019, 19(6), 419-433.
[http://dx.doi.org/10.2174/1566524019666190509102620 PMID: 31072290]
[23]
Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheese-man, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.P.; Izmaylov, A.F.; Bloino, J.; Zheng, G.; Sonnen-berg, J.L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J.A.; Peralta, J.E.; Ogliaro, F.; Bearpark, M.; Heyd, J.J.; Brothers, E.; Kudin, K.N.; Star-overov, V.N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J.C.; Iyengar, S.S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J.M.; Klene, M.; Knox, J.E.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Martin, R.L.; Morokuma, K.; Zakrzewski, V.G.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Dapprich, S.; Daniels, A.D.; Farkas, O.; Foresman, J.B.; Ortiz, J.V.; Cioslowski, J.; Fox, D.J. Gaussian, Inc., Wallingford CT; , 2009.
[24]
Soto-Rojo, R.; Baldenebro-López, J.; Flores-Holguín, N.; Glossman-Mitnik, D. J. Mol. Model., 2014, 20(8), 2378.
[http://dx.doi.org/10.1007/s00894-014-2378-2 PMID: 25060149]
[25]
Frisch, A.; Nielson, A.B.; Holder, A.J. GAUSSVIEW User Manual; Gaussian Inc.: Pittsburgh, PA, 2000.
[26]
Weinhold, F.; Landis, C.R. Neutral Bond Orbitals and Extensions of Localized, 2001.
[27]
Parry, P.R.; Wang, C.; Batsanov, A.S.; Bryce, M.R.; Tarbit, B. J. Org. Chem., 2002, 67(21), 7541-7543.
[http://dx.doi.org/10.1021/jo020388b PMID: 12375993]
[28]
Murray, J.; Politzer, P. Comput Mol Sci., 2011, 1, 153-163.
[http://dx.doi.org/10.1002/wcms.19]
[29]
Proutiere, F.; Aufiero, M.; Schoenebeck, F. J. Am. Chem. Soc., 2012, 134(1), 606-612.
[http://dx.doi.org/10.1021/ja209424z PMID: 22132686]
[30]
Joshaghani, M.; Daryanavard, M.; Rafiee, E.; Nadri, S. J. Organomet. Chem., 2008, 693, 3135-3140.
[http://dx.doi.org/10.1016/j.jorganchem.2008.07.003]
[31]
Mora, M.; Jimenez-Sanchidrian, C.; Ruiz, J.R. J. Mol. Catal. Chem., 2008, 285, 79-83.
[http://dx.doi.org/10.1016/j.molcata.2008.01.031]
[32]
Ozgen, M.; Reese, R.N.; Tulio, A.Z.; Scheerens, J.C.; Miller, A.R. J. Agric. Food Chem., 2006, 285, 79-83.
[33]
Alonso, F.; Beletskaya, I.P.; Yus, M. Tetrahedron, 2008, 64, 3047-3101.
[http://dx.doi.org/10.1016/j.tet.2007.12.036]
[34]
Sheikhi, M.; Shahab, S.; Khaleghian, M.; Hajikolaee, F.H.; Balakhanava, I.; Alnajjar, R. J. Mol. Struct., 2018, 1160, 479-478.
[http://dx.doi.org/10.1016/j.molstruc.2018.01.005]
[35]
Shahab, S.; Sheikhi, M.; Khaleghian, M.; Balakhanava, I. J. Struct. Chem., 2019, 38, 37-52.
[36]
Sheikhi, M.; Shahab, S.; Khaleghian, M.; Kumar, R. Appl. Surf. Sci., 2018, 434, 504-513.
[http://dx.doi.org/10.1016/j.apsusc.2017.10.154]
[37]
Shahab, S.; Sheikhi, M.; Filippovich, L.; Ihnatovich, Z.; Koroleva, E.; Drachilovskaya, M.; Atroshko, M.; Pazniak, A. Dyes Pigments, 2019.
[http://dx.doi.org/10.1016/j.dyepig.2019.107647]
[38]
Rasheed, T.; Rasool, N.; Noreen, M.; Gull, Y.; Zubair, M.; Ullah, A.; Rana, U.A. J. Sulfur Chem., 2015, 36, 240-250.
[http://dx.doi.org/10.1080/17415993.2015.1020493]
[39]
Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radic. Biol. Med., 1999, 26(9-10), 1231-1237.
[http://dx.doi.org/10.1016/S0891-5849(98)00315-3] [PMID: 10381194]

Rights & Permissions Print Cite
Article Metrics
9
1
© 2024 Bentham Science Publishers | Privacy Policy