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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Synthesis, Antimicrobial, Antioxidant Evaluation, and DFT Estimation of some New Cyclohexenone Derivatives Derived from Benzyloxy Chalcones

Author(s): Media Noori Abdullah*

Volume 20, Issue 7, 2023

Published on: 10 March, 2023

Page: [812 - 820] Pages: 9

DOI: 10.2174/1570179420666230126103401

Price: $65

Abstract

Background: New cyclohexenone derivatives candidates were designed to discover their antioxidant and antibacterial activity potentials, respectively.

Methods: Aldehydes with the diverse functional group were prepared from 4-hydroxy benzaldehyde and benzyl bromide and converted to chalcones by reaction with 4-substituted benzophenones and 2-acetyl naphthalene. When chalcone derivatives were subjected to ethyl acetoacetate, it produced new cyclohexenone derivatives through NaOH- catalyzed addition-ring closure reaction. The new compound structures were strengthened by their spectral information. The new compounds are examined for in vitro antifungal and antibacterial actions through broth microdilution technique, and they exhibited potential responses against various bacteria and fungi.

Results: As a result, composites with (-F) group as a substituent on para position were established to be the forceful derivatives against S. aureus, E. coli organism, and C Albicans since this compound could inhibit the microbial and Fungai growth at lower concentrations compared to the standards (Ciprofloxacin HCl, and Fluconazole).

Conclusion: DPPH radical scavenging experiments were used to evaluate proton donating antioxidant effects; it was exposed that compound 7c has the most significant antioxidant activity, while less than the standard ascorbic acid. Finally, HOMO-LUMO was calculated, which represents the quantum mechanical calculations of energies and conducted by the theory of density functional (DFT) method based on the level of (B3LYP) with 6-31G (d, p) basis set.

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[1]
Kennedy, A.R.; Kipkorir, Z.R.; Muhanji, C.I.; Okoth, M.O. 4-(Benzyloxy)benzaldehyde. Acta Crystallogr. Sect. E Struct. Rep. Online, 2010, 66(8), o2110.
[http://dx.doi.org/10.1107/S1600536810027200] [PMID: 21588401]
[2]
Kun, H.; Murat, O.; Mahmoud, M. Explorations of crystalline effects on 4-(benzyloxy) benzaldehyde properties. J. Zeitschrift für Naturforschung A, 2015, 70(12), 1013-1018.
[http://dx.doi.org/10.1515/zna-2015-0134]
[3]
Ibrahim, A.I.M.; Ikhmais, B.; Batlle, E.; AbuHarb, W.K.; Jha, V.; Jaradat, K.T.; Jiménez, R.; Pequerul, R.; Parés, X.; Farrés, J.; Pors, K. Design, synthesis, biological evaluation and in silico study of benzyloxybenzaldehyde derivatives as selective ALDH1A3 inhibitors. Molecules, 2021, 26(19), 5770.
[http://dx.doi.org/10.3390/molecules26195770] [PMID: 34641313]
[4]
Gomes, M.; Muratov, E.; Pereira, M.; Peixoto, J.; Rosseto, L.; Cravo, P.; Andrade, C.; Neves, B. Chalcone derivatives: Promising starting points for drug design. Molecules, 2017, 22(8), 1210.
[http://dx.doi.org/10.3390/molecules22081210] [PMID: 28757583]
[5]
Gaonkar, S.L.; Vignesh, U.N. Synthesis and pharmacological properties of chalcones: A review. Res. Chem. Intermed., 2017, 43(11), 6043-6077.
[http://dx.doi.org/10.1007/s11164-017-2977-5]
[6]
Attarde, M.; Vora, A.; Varghese, A.; Kachwala, Y. Synthesis and evaluation of chalcone derivatives for its alpha amylase inhibitory activity. Org. Chem. An Indian J., 2014, 10, 192.
[7]
Josefina, H.; Cristina, W.; Alejandra, M.; Marko, J.; Carlos, H.P.; Stanislav, G.; Felicitas de Tezanos, P.; Natalia, C.; Mariel, M. Chalcone derivatives: Synthesis, in vitro and in vivo evaluation of their anti-anxiety, anti-depression and analgesic effects. Heliyon, 2019, 5, e01376.
[8]
Jasim, H.A.; Nahar, L.; Jasim, M.A.; Moore, S.A.; Ritchie, K.J.; Sarker, S.D. Chalcones: Synthetic chemistry follows where nature leads. Biomolecules, 2021, 11(8), 1203.
[http://dx.doi.org/10.3390/biom11081203] [PMID: 34439870]
[9]
Barakat, A.; Al-Majid, A.M.; Soliman, S.M.; Mabkhot, Y.N.; Ali, M.; Ghabbour, H.A.; Fun, H.K.; Wadood, A. Structural and spectral investigations of the recently synthesized chalcone (E)-3-mesityl-1-(naphthalen-2-yl) prop-2-en-1-one, a potential chemotherapeutic agent. Chem. Cent. J., 2015, 9(1), 35.
[http://dx.doi.org/10.1186/s13065-015-0112-5] [PMID: 26106444]
[10]
Varun, A.; Pragi, A.; Lamba, H.S. Synthesis and evaluation of chalcone derivatives of 2-acetyl naphthalene for antifungal and antibacterial activity. Pharm. Lett., 2012, 4(2), 554.
[http://dx.doi.org/10.1186/s13065-015-0112-5]
[11]
Bonyad, A.M. Synthesis of chalcones from acetone and tetrazole and 2-acetyl naphthalene assisted by microwave. Engin. Technol. Quarterly Rev., 2020, 3(1), 16-22.
[12]
Chu, H.W.; Sethy, B.; Hsieh, P.W.; Horng, J.T. Identification of potential drug targets of broad-spectrum inhibitors with a michael acceptor moiety using shotgun proteomics. Viruses, 2021, 13(9), 1756.
[http://dx.doi.org/10.3390/v13091756] [PMID: 34578337]
[13]
Monga, V.; Goyal, K.; Steindel, M.; Malhotra, M.; Rajani, D.P.; Rajani, S.D. Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents. Med. Chem. Res., 2014, 23(4), 2019-2032.
[http://dx.doi.org/10.1007/s00044-013-0803-1]
[14]
Yakup, B.; Esra, F.; Mustafa, C. Cyclohexenone through addition of ethyl acetoacetate to 3-aryl-1-(thiophen-3-yl)prop-2-en-1-one derivatives. J. Chem., 2010, 63, 1.
[15]
Gheorghe, R. Cyclohexenone through addition of ethyl acetoacetate to chalcones derived from 2-acetylthiophene. Acta Chim. Slov., 2004, 51, 537.
[16]
Lopes, R.C.V.; Oliveira, M.C.F.; Lemos, T.L.G.; Mattos, M.C. A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: Influence of quaternary ammonium cations as phase transfer catalysts. J. Braz. Chem. Soc., 2005, 16(5), 1048-1053.
[http://dx.doi.org/10.1590/S0103-50532005000600023]
[17]
Shin, S.Y.; Park, J.; Jung, Y.; Lee, Y.H.; Koh, D.; Yoon, Y.; Lim, Y. Anticancer activities of cyclohexenone derivatives. Appl. Biolog. Chem., 2020, 63(1), 82.
[http://dx.doi.org/10.1186/s13765-020-00567-1]
[18]
Badshah, A.; Nazar, M.F.; Mahmood, A.; Ahmed, W.; Abdullah, M.I.; Zafar, M.N.; Rana, U.A. Synthesis, characterization of novel cyclohexenone derivatives and computation of their optical response. J. Mol. Struct., 2014, 1071, 103-110.
[http://dx.doi.org/10.1016/j.molstruc.2014.04.074]
[19]
Anil, N.M.; Hongqi, L.; Yathirajan, H.S. Synthesis, characterization and antimicrobial study of some new cyclohexenone derivatives. Int. J. Chem., 2010, 2, 114.
[20]
Kanagarajan, V.; Ezhilarasi, M.R.; Thanusu, J.; Gopalakrishnan, M. Activated fly ash-catalyzed synthesis of naphthyl-substituted cyclohexenone carboxylates, indazolonols, and nitro hydrazones in “ dry media. Green Chem. Lett. Rev., 2011, 4(4), 355-368.
[http://dx.doi.org/10.1080/17518253.2011.573811]
[21]
Shikar, S.O.; Media, N.A. Synthesis of novel michael adducts and study of their antioxidant and antimicrobial activities. Chem. Rev. Lett., 2022, 5, 226.
[http://dx.doi.org/10.22034/CRL.2022.350315.1176]
[22]
Satishkumar, D.T.; Vekariya, P.B.; Ghetiya, R.M.; Bhavesh, L.D.; Hitendra, J. Synthesis and biological study of some new chalcone and pyrazole derivatives. Indian J. Chem. Sec. B 52B, 2013, 6, 807.
[23]
Sreevidya, T.; Narayana, B.; Yathirajan, H. Synthesis and characterization of some chalcones and their cyclohexenone derivatives. Open Chem., 2010, 8(1), 174-181.
[http://dx.doi.org/10.2478/s11532-009-0124-x]
[24]
Aksöz, B.E.; Ertan, R. Spectral properties of chalcones II. Fabad J. Pharm. Sci., 2012, 37, 205.
[25]
Wiegand, I.; Hilpert, K.; Hancock, R.E.W. Agar and broth dilution methods to determine the Minimal Inhibitory Concentration (MIC) of antimicrobial substances. Nat. Protoc., 2008, 3(2), 163-175.
[http://dx.doi.org/10.1038/nprot.2007.521] [PMID: 18274517]
[26]
Sangar, A.H.; Media, N.A.; Dara, M.A. Synthesis, in vitro antimicrobial assay and molecular docking studies of some new symmetrical bis-schiff bases and their 2-azetidinones. Zanco J. Pure Appl. Sci., 2021, 33(2), 34.
[http://dx.doi.org/10.21271/ZJPAS.33.2.4]
[27]
Hassan, S.; Media, N.A.; Dara, M.A. An efficient one-pot three-component synthesis, molecular docking, ADME and DFT predictions of new series thiazolidin-4-one derivatives bearing a sulfonamide moiety as potential antimicrobial and antioxidant agents. Egypt. J. Chem., 2022, 65, 133-146.
[http://dx.doi.org/10.21608/ejchem.2022.104381.4819]
[28]
Hassan, S.A.; Abdullah, M.N.; Aziz, D.M. Synthesis of new series bis-3-chloro-β-lactam derivatives from symmetrical bis-schiff bases as effective antimicrobial agents with molecular docking studies. Sci. J. Uni. Zakho., 2021, 9(3), 128-137.
[http://dx.doi.org/10.25271/sjuoz.2021.9.3.830]
[29]
Nakamura, C.; Kawasaki, N.; Miyataka, H.; Jayachandran, E.; Kim, I.H.; Kirk, K.L.; Taguchi, T.; Takeuchi, Y.; Hori, H.; Satoh, T. Synthesis and biological activities of fluorinated chalcone derivatives. Bioorg. Med. Chem., 2002, 10(3), 699-706.
[http://dx.doi.org/10.1016/S0968-0896(01)00319-4]
[30]
Sangar, A.H.; Media, N.A. Synthesis, spectroscopic study and biological activity of some new heterocyclic compounds derived from sulfadiazine. Zanco J. Pure Appl. Sci., 2019, 31(6), 92.
[http://dx.doi.org/10.21271/ZJPAS.31.6.10]
[31]
Mumit, M.A.; Pal, T.K.; Alam, M.A.; Islam, M.A.; Paul, S.; Sheikh, M.C. DFT studies on vibrational and electronic spectra, HOMO–LUMO, MEP, HOMA, NBO and molecular docking analysis of benzyl-3-N-(2,4,5-trimethoxyphenylmethylene)hydrazinecarbodithioate. J. Mol. Struct., 2020, 1220, 128715.
[http://dx.doi.org/10.1016/j.molstruc.2020.128715] [PMID: 32834109]

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