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

Spectroscopic Investigations and DFT Studies of Synthesized 4- Acetamidophenyl 3,4,5-Trimethoxybenzoate and 4-acetyl phenyl 3,4,5- trimethoxybenzoate a Novel Conjugate of Gallic Acid

Author(s): Sangeeta Srivastava*, Nadeem Ahmad Ansari and Sadaf Aleem

Volume 18, Issue 2, 2021

Published on: 18 August, 2020

Page: [134 - 142] Pages: 9

DOI: 10.2174/1570178617999200818205347

Price: $65

Abstract

Gallic acid is abundantly found in amla (Phyllanthus emblica), a deciduous of the family phyllanthaceae. Gallic acid, the major constituent of the plant, was methylated to 3,4,5 trimethoxy gallic acid, which then underwent steglich esterification first with paracetamol and then with 4-hydroxy acetophenone to yield 4-acetamidophenyl 3,4,5-trimethoxybenzoate and 4-acetyl phenyl 3,4,5-trimethoxybenzoate “respectively”. 1H NMR, 13C NMR, UV, FT-IR and mass spectroscopy were used to characterize the synthesized compounds. Density functional theory (B3YLP) using a 6-31G (d,p) basis set has been used for quantum chemical calculations. AIM (Atom in a molecule) approach depicted weak molecular interactions within the molecules, whereas the reactive site and reactivity within the molecule were examined by global and local reactivity descriptors. The HOMO and LUMO energies and frontier orbital energy gaps were calculated by time dependent DFT approach using the IEFPCM model. A small value for the HOMO-LUMO energy gap indicated that easier charge transfer occurs within compound 4. The nucleophilic and electrophilic reactivity was determined by MEP (molecular electrostatic potential) experiment. Polarizability, dipole moment, and first hyperpolarizability values were calculated to depict the NLO (nonlinear optical) property of both the synthesized compounds. The antimicrobial activity was also carried out and broad-spectrum antibacterial activity against several strains of bacteria and certain unicellular fungi were exhibited by synthesized compound 3.

Keywords: Steglich esterification, spectroscopy, bioevaluation, hyperpolarizability, MEP and AIM.

« Previous Next »
Graphical Abstract

[1]
Camins, B.C.; King, M.D.; Wells, J.B.; Googe, H.L.; Patel, M.; Kourbatova, E.V.; Blumberg, H.M. Infect. Control Hosp. Epidemiol., 2009, 30(10), 931-938.
[http://dx.doi.org/10.1086/605924] [PMID: 19712032]
[2]
Wong, D.G.; Spence, J.D.; Lamki, L.; Freeman, D.; McDonald, J.W. Lancet, 1986, 1(8488), 997-1001.
[http://dx.doi.org/10.1016/S0140-6736(86)91271-7] [PMID: 2871333]
[3]
Afsar, T.; Khan, M.R.; Razak, S.; Ullah, S.; Mirza, B. BMC Complement. Altern. Med., 2015, 15, 136.
[http://dx.doi.org/10.1186/s12906-015-0658-8] [PMID: 25928288]
[4]
Dhale, DA; Mogle, UP Science research reporter, 2011, 1(3), 138-142.
[5]
Stonik, V.A. Russ. Chem. Rev., 2001, 70, 673-715.
[http://dx.doi.org/10.1070/RC2001v070n08ABEH000679]
[6]
Grant Newey, S.; Betty, W.; Faye, S. J. Agric. Food Chem., 1967, 15, 132.
[http://dx.doi.org/10.1021/jf60149a017]
[7]
Grundhöfer, P.; Niemetz, R.; Schilling, G.; Gross, G.G. Phytochemistry, 2001, 57(6), 915-927.
[http://dx.doi.org/10.1016/S0031-9422(01)00099-1] [PMID: 11423141]
[8]
Klein, E.; Weber, N. J. Agric. Food Chem., 2001, 49(3), 1224-1227.
[http://dx.doi.org/10.1021/jf000725m] [PMID: 11312840]
[9]
Mahadevan, A.; Reddy, M.K. J. Plant Pathol., 1968, 74, 87.
[10]
Isoyama, N.; Okazoe, K.; Ichimura, N.; Sugihara, Y. Nichidai Igaku Zasshi, 1968, 27, 270.
[11]
Thompson, P.E.; Moore, A.M.; Reinertson, W. J. Antibiot. Khimioter., 1953, 3, 399.
[12]
Serrano, A.; Palacios, C.; Roy, G.; Cespon, C.; Villa, M.L.; Nocito, M.; Gonzales-Porque, P. Arch. Biochem.,
[13]
Sharma, S.; Wyatt, G.P.; Steele, V.E. Methods Cell Sci., 1997, 19, 4548.
[14]
Kim, Y. J. Biol. Pharm. Bull., 2007, 30(6), 1052-1055.
[http://dx.doi.org/10.1248/bpb.30.1052] [PMID: 17541153]
[15]
Chi, A.; Norden, A.D.; Wen, P.Y. Expert Rev. Anticancer Ther., 2007, 7(11), 1537-1560.
[http://dx.doi.org/10.1586/14737140.7.11.1537] [PMID: 18020923]
[16]
Kastan, M.B.; Onyekwere, O.; Sidransky, D.; Vogelstein, B.; Craig, R.W. Cancer Res., 1991, 51(23 Pt 1), 6304-6311.
[PMID: 1933891]
[17]
Chen, H.M.; Wu, Y.C.; Chia, Y.C.; Chang, F.R.; Hsu, H.K.; Hsieh, Y.C.; Chen, C.C.; Yuan, S.S. Cancer Lett., 2009, 286(2), 161-171.
[http://dx.doi.org/10.1016/j.canlet.2009.05.040] [PMID: 19589639]
[18]
Locatelli, C. Bioorg. Med. Chem., 2008, 16, 3791.
[http://dx.doi.org/10.1016/j.bmc.2008.01.049] [PMID: 18295493]
[19]
Mamdouh, S. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2012, 94, 256-264.
[20]
Srivastava, S.; Ansari, N.A.; Aleem, S. J. Biol.Chem.Research, 2019, 36(1), 14-23.
[21]
Koopmans, T. Physica, 1934, 1, 104-113.
[http://dx.doi.org/10.1016/S0031-8914(34)90011-2]
[22]
Pearson, R.G. J. Am. Chem. Soc., 1985, 107, 6801.
[http://dx.doi.org/10.1021/ja00310a009]
[23]
Pearson, R.G. J. Org. Chem., 1989, 54, 1423-1430.
[http://dx.doi.org/10.1021/jo00267a034]
[24]
Parr, R.G.; Pearson, R.G. J. Am. Chem. Soc., 1983, 105, 7512-7516.
[http://dx.doi.org/10.1021/ja00364a005]
[25]
Greelings, P.; Proft, F.D.; Langenaeker, W. Chem. Rev., 2003, 103, 1793-1873.
[http://dx.doi.org/10.1021/cr990029p] [PMID: 12744694]
[26]
Gupta, V.P.; Sharma, A.; Virdi, A.; Ram, V. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2006, 64(1), 57-67.
[http://dx.doi.org/10.1016/j.saa.2005.06.045] [PMID: 16098792]
[27]
Rozas, I.; Alkorta, I.; Elguero, J. J. Am. Chem. Soc., 2000, 122, 11154-11161.
[http://dx.doi.org/10.1021/ja0017864]
[28]
Kolinsky, P.V. Opt. Eng., 1992, 31, 1676-1684.
[http://dx.doi.org/10.1117/12.58844]
[29]
Eaton, D.F. Science, 1991, 253(5017), 281-287.
[http://dx.doi.org/10.1126/science.253.5017.281] [PMID: 17794694]
[30]
Sundaraganesan, N.; Kavitha, E.; Sebastian, S.; Cornard, J.P.; Martel, M. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2009, 74(3), 788-797.
[http://dx.doi.org/10.1016/j.saa.2009.08.019] [PMID: 19729338]
[31]
Krishnakumar, V.; Manohar, S. Molecular and biomoleculr Spectroscopy. R., 2008, 71110-71115.
[32]
Silverstein, R.M.; Webster, F.X. Spectrometric Identification of Organic Compounds, sixth Edi; Jon Willey Sons Inc.: New York, 1963.
[33]
Srivastava, S.; Gupta, P.; Singh, R.P.; Jafri, A.; Arshad, M.; Banerjee, M. J. Mol. Struct., 2017, 1141, 678-686.
[http://dx.doi.org/10.1016/j.molstruc.2017.04.008]
[34]
Srivastava, S.; Ansari, N. Aleem S. J. Mol. Struct, 2019, 1195, 231-245.
[http://dx.doi.org/10.1016/j.molstruc.2019.05.107]

Rights & Permissions Print Cite
Article Metrics
19
1
© 2024 Bentham Science Publishers | Privacy Policy