Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potentional anticonvulsant agents

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Published: Apr 29, 2019
Keywords:
Succinimide, Electronic effect, Spectroscopic analysis, Quantum chemical calculation

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Jelena Petković Cvetković
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120, Belgrade, Serbia
Bojan Božić
Institute of Physiology and Biochemistry, Faculty of Biology, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia
Nebojša Banjac
Faculty of Agriculture, Food Technology and Biochemistry, University of Belgrade, Nemanjina 6, 11080, Belgrade, Zemun, Serbia
Jelena Lađarević
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120, Belgrade, Serbia
Vesna Vitnik
Department of Chemistry, ICTM, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia
Željko Vitnik
Department of Chemistry, ICTM, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia
Nataša Valentić
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120, Belgrade, Serbia
Gordana Ušćumlić
Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120, Belgrade, Serbia

Abstract

Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions using the microwave irradiation. All obtained compounds were characterized by the UV, FT-IR, 1H and 13С NMR spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on the spectroscopic data has been analyzed applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra have been performed. DFT calculated data of the investigated succinimides are obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed.

Article Details

How to Cite
[1]
J. Petković Cvetković, “Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potentional anticonvulsant agents”, Hem Ind, vol. 73, no. 2, pp. 125–137, Apr. 2019, Accessed: Nov. 24, 2024. [Online]. Available: https://www.ache-pub.org.rs/index.php/HemInd/article/view/493
Issue
Vol. 73 No. 2 (2019)
Section
Applied Chemistry
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How to Cite

[1]
J. Petković Cvetković, “Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potentional anticonvulsant agents”, Hem Ind, vol. 73, no. 2, pp. 125–137, Apr. 2019, Accessed: Nov. 24, 2024. [Online]. Available: https://www.ache-pub.org.rs/index.php/HemInd/article/view/493

References

References

Hargreaves MK, Pritchard JG, Dave HR. Cyclic carboxylic monoimides. Chem Rev. 1970; 70: 439 – 469.

Kamiński K, Obniska J. Design, synthesis, and anticonvulsant activity of N-phenylamino derivatives of 3,3-dialkyl-pyrrolidine-2,5-diones and hexahydro-isoindole-1,3-diones. Bioorgan Med Chem. 2008; 16: 4921 – 4931.

Kamiński K, Rzepka S, Obniska J. Synthesis and anticonvulsant activity of new 1-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]pyrrolidine-2,5-diones. Bioorgan Med Chem Lett. 2011; 21: 5800 – 5803.

Patsalos PN. Properties of antiepileptic drugs in the treatment of idiopathic generalized epilepsies. Epilepsia. 2005; 46: 140–148.

Porter RJ, Penry JK, Lacy JR, Newmark ME, Kupferberg HJ. Plasma concentrations of phensuximide, methsuximide, and their metabolites in relation to clinical efficacy. Neurology. 1979; 29: 1509 – 1513.

Jensen PB, Sokilde B, Carstensen EV, Langer SW, Creighton A, Sehested M, Jensen L. Succinimide and maleimide derivatives and their use as topoisomerase II catalytic inhibitors. EP 1373494, 2004

Korhalkar AA, Khadse BG, Sengupta SR. Synthesis of 2-hetero/aryl-N-(p-fluorobenzene) succinimide derivatives as antitubercular agents. Indian Drugs. 1992; 29: 306 – 307.

Khadilkar BM, Bhayade SR. Synthesis and hypotensive activity of some succinimide derivatives. Indian J Chem B. 1993; 32: 338 – 342.

Shetgiri NP, Nayak BK. Synthesis and antimicrobial activity of some succinimides. Indian J Chem B. 2005; 44B: 1933 – 1936.

Zentz F, Guillou RL, Labia R, Sirot D, Linard B, Valla A. Syntheses, in vitro antibacterial and cytotoxic activities of a series of 3-substituted succinimides. Farmaco. 2004; 59: 879 – 886.

Bansode TN, Shelke JV, Dongre VG. Synthesis and antimicrobial activity of some new N-acyl substituted phenothiazines. Eur J Med Chem. 2009; 44: 5094 – 5098.

Sharir M. Succinimide derivatives as ocular hypotensive agents. WO 2007057889, 2007.

Prince DA. Succinimides and oxazolidinediones for treating tremor. US 4981867, 1991.

Kumar S, Prakash S, Gupta K, Dongre A, Balaram P, Balaram H. Unexpected functional implication of a stable succinimide in the structural stability of Methanocaldococcus jannaschii glutaminase. Nat Commun. 2016; 7: 12798.

Takahashi O, Kirikoshi R, Manabe N. Roles of intramolecular and intermolecular hydrogen bonding in a three-water-assisted mechanism of succinimide formation from aspartic acid residues. Molecules. 2014; 19: 11440 – 11452.

Grassi L, Regl C, Wildner S, Gadermaier G, Huber CG, Cabrele C, Schubert M. Complete NMR Assignment of succinimide and its detection and quantification in peptides and intact proteins. Anal Chem. 2017; 89: 11962 – 11970.

Kleemann A, Engel J. Pharmaceutical Substances: Syntheses, Patents, Applications. Stuttgart, Germany: Georg Thieme Verlag; 2001.

Liu SL, Li Y, Guo JR, Yang GC, Li XH, Gong JF, Song MP. An approach to 3-(Indol-2-yl)succinimide derivatives by manganese-catalyzed C-H activation. Org Lett. 2017; 19: 4042 – 4045.

Chauhan P, Kaur J, Chimni SS. Asymmetric organocatalytic addition reactions of maleimides. A promising approach towards the synthesis of chiral succinimide derivatives. Chem-Asian J. 2013; 8: 328 – 346.

Han SH, Kim S, De U, Mishra NK, Park J, Sharma S, Kwak JH, Han S, Kim HS, Kim IS. Synthesis of succinimide-containing chromones, naphthoquinones, and xanthones under Rh(III) catalysis: evaluation of anticancer activity. J Org Chem. 2016; 81: 12416 – 12425.

Kishikawa K, Furukawa Y, Watanabe T, Kohri M, Taniguchi T, Kohmoto S. Why chiral tartaric imide derivatives give large helical twisting powers in nematic liquid crystal phases: substituent-effect approach to investigate intermolecular interactions between dopant and liquid crystalline molecules. Liq Cryst. 2017; 44: 956 – 968.

Shirini F, Khaligh NG. Succinimide-N-sulfonic acid: An efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions. Dyes Pigments. 2012; 95: 789 – 794.

Peng H, Kather M, Rübsam K, Jakob F, Schwaneberg U, Pich A. Water-soluble reactive copolymers based on cyclic N-vinylamides with succinimide side groups for bioconjugation with proteins. Macromolecules. 2015; 48: 4256 – 4268.

Doll KM, Shogrent RL, Holser RA, Willett JL, Swift G. Polymerization of L-aspartic acid to polysuccinimide and copoly(succinimide-aspartate) in supercritical carbon dioxide. Lett Org Chem. 2005; 2: 687 – 689.

Hughes JP, Rees S, Kalindjian SB, Philpott KL. Principles of early drug discovery. Brit J Pharmacol. 2011; 162: 1239 – 1249.

Milosevic NP, Kojic V, Curcic J, Jakimov D, Milic N, Banjac N, Uscumlic G, Kaliszan R. Evaluation of in silico pharmacokinetic properties and in vitro cytotoxic activity of selected newly synthesized N-succinimide derivatives. J Pharmaceut Biomed. 2017; 137: 252 – 257.

Perisic-Janjic N, Kaliszan R, Milosevic N, Uscumlic G, Banjac N. Chromatographic retention parameters in correlation analysis with in silico biological descriptors of a novel series of N-phenyl-3-methyl succinimide derivatives. J Pharmaceut Biomed. 2013; 72: 65 – 73.

Perisic-Janjic N, Kaliszan R, Wiczling P, Milosevic N, Uscumlic G, Banjac N. Reversed-phase TLC and HPLC retention data in correlation studies with in silico molecular descriptors and druglikeness properties of newly synthesized anticonvulsant succinimide derivatives. Mol Pharmaceutics. 2011; 8: 555 – 563.

Chamundeeswaria SPV, Samuela EJJ, Sundaraganesan N. Quantum mechanical and spectroscopic (FT-IR, FT-Raman, 13C, 1H and UV) investigations of antiepileptic drug Ethosuximide. Spectrochim Acta A. 2011; 83: 478 – 489.

Vitnik VD, Vitnik ŽJ, Banjac NR, Valentić NV, Ušćumlić GS, Juranić IO. Quantum mechanical and spectroscopic (FT-IR, 13C, 1H NMR and UV) investigations of potent antiepileptic drug 1-(4-chlorophenyl)-3-phenylsuccinimide. Spectrochim Acta A. 2014; 117: 42 – 53.

Banjac NR, Božić BÐ, Mirković JM, Vitnik VD, Vitnik ŽJ, Valentić NV, Ušćumlić GS. Experimental and theoretical study on the structure-property relationship of novel 1-aryl-3-methylsuccinimides. J Mol Struct. 2017; 1129: 271 – 282.

Miller CA, Long LM. Anticonvulsants. I. N-R-α-R1-α-phenylsuccinimides. J Am Chem Soc. 1951; 73: 4895 – 4898.

Miller CA, Long LM. Anticonvulsants. III. A study of N,α,β-trialkylsuccinimides. J Am Chem Soc. 1953; 75: 373 – 375.

Katritzky AR, Nair SK, Witek RM, Hutchins SM. Synthesis of 3,3-diarylpyrrolidines from diaryl ketones. ARKIVOC. 2003; V: 9 – 18.

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 09, Revision D.01. Wallingford CT: Gaussian, Inc.; 2009.

Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993; 98: 5648 – 5652.

Zhao Y, Truhlar DG. Density functionals with broad applicability in chemistry. Accounts Chem Res. 2008; 41: 157 – 167.

Scott AP, Radom L. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Moeller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem. 1996; 100: 16502 – 16513.

Dennington R, Keith T, Millam J. GaussView, Version 5.0.9. Shawnee Mission, Semichem Inc., KS; 2009.

Cossi M, Rega M, Scalmani G, Barone V. Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model. J Comput Chem. 2003; 24: 669 – 681.

Hammett LP. Effect of structure upon the reactions of organic compounds. Benzene derivatives. J Am Chem Soc. 1937; 59: 96 – 103.

Brown H, Okamoto Y. Electrophilic Substituent Constants. J Am Chem Soc. 1958; 80: 4979 – 4987.

Petković Cvetković J, Božić B, Banjac N, Petrović J, Soković M, Vitnik V, Vitnik Ž, Ušćumlić G, Valentić N. Synthesis, antimicrobial activity and quantum chemical investigation of novel succinimide derivatives. J Mol Struct. 2019; 1181: 148 –156.

Fleming I. Frontier Orbitals and Organic Chemical Reactions. New York, USA: John Wiley and Sons; 1976.

Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev. 1997; 23: 3 – 25.

Remko M, Swary M, Bickelhaupt FM. Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives. Bioorgan Med Chem. 2006; 14: 1715 – 1728.

Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem. 2002; 45: 2615 – 2623.

Ghose AK, Viswanadhan VN, Wendoloski JJ. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. a qualitative and quantitative characterization of known drug databases. J Comb Chem. 1999; 1: 55 – 68.

Molinspiration (2019). Calculation of Molecular Properties and Bioactivity Score. Molinspiration Cheminformatics [online].

Sinha L, Karabacak M, Narayan V, Cinar M, Prasad O. Molecular structure, electronic properties, NLO, NBO analysis and spectroscopic characterization of Gabapentin with experimental (FT-IR and FT-Raman) techniques and quantum chemical calculations. Spectrochim Acta A. 2013; 109: 298 – 307.

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