Nucleophilic Substitution Reaction of Imidazole with Various 2-Bromo-1-arylethanone Derivatives: A Computational Study

Year 2019, Volume: 23 Issue: 3, 322 - 332, 01.06.2019

Taner Erdoğan , Fatma Oğuz Erdoğan

https://doi.org/10.16984/saufenbilder.418343

Abstract

In
this study, it was intended to investigate the reactions between imidazole and
2-bromo-1-arylethanones such as 2-bromoacetophenone,
2-bromo-1-(4-chlorophenyl)ethan-1-one,
2-bromo-1-(2,4-dichlorophenyl)ethan-1-one and 2-bromo-1-(furan-2-yl)ethan-1-one,
computationally. In the study, some Density Functional Theory (DFT)
calculations have been performed on the chemical species involved in the
investigated chemical reactions. DFT calculations have been performed at DFT
B3LYP (Becke, three-parameter, Lee-Yang-Parr) level of theory using 6-31G(d),
6-31G(d,p), 6-311G(d,p) and 6-311+G(2d,p) basis sets. Single Point Energy (SPE)
calculations, geometry optimizations, vibrational analysis, Frontier Molecular
Orbital (FMO) calculations, global reactivity descriptor determinations,
Molecular Electrostatic Potential (MEP) map calculations and estimation of the
nuclear magnetic shielding tensors have been carried out at the same levels of
theory. In ¹H-NMR calculations, CSGT (Continuous Set of Gauge
Transformations) and GIAO (Gauge-Independent Atomic Orbital) models were used
and experimental data have been compared with the computationally obtained
data.

Keywords

imidazole, phenacyl bromide, computational chemistry, azoles, DFT

References

• Guven, O.O., T. Erdogan, H. Goker, and S. Yildiz, "Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers." Bioorganic & Medicinal Chemistry Letters, 17(8), 2233-2236, 2007.
• Abdel-Megid, M., "Reactivity of functionally substituted azoles towards electrophiles. Novel synthesis of thienylazoles and phenylazoles." Synthetic Communications, 33(1), 153-160, 2003.
• Amir, M., I. Ali, and M.Z. Hassan, "Imidazole Incorporated Semicarbazone Derivatives as a New Class of Anticonvulsants: Design, Synthesis and In-Vivo Screening." Medicinal Chemistry, 9(4), 571-580, 2013.
• Belai, I., B. Darvas, K. Bauer, and M.H.T. Eldin, "EFFECTS OF ANTI-ECDYSTEROID AZOLE ANALOGS OF METYRAPONE ON THE LARVAL DEVELOPMENT OF THE FLESHFLY, NEOBELLIERIA-BULLATA." Pesticide Science, 44(3), 225-232, 1995.
• De Vita, D., F. Pandolfi, R. Cirilli, L. Scipione, R. Di Santo, L. Friggeri, M. Mori, D. Fiorucci, G. Maccari, R.S.A. Christopher, C. Zamperini, V. Pau, A. De Logu, S. Tortorella, and M. Botta, "Discovery of in vitro antitubercular agents through in silico ligand-based approaches." European Journal of Medicinal Chemistry, 121, 169-180, 2016.
• Dogan, I.S., S. Sarac, S. Sari, D. Kart, S.E. Gokhan, I. Vural, and S. Dalkara, "New azole derivatives showing antimicrobial effects and their mechanism of antifungal activity by molecular modeling studies." European Journal of Medicinal Chemistry, 130, 124-138, 2017.
• Florentino, L., F. Aznar, and C. Valdes, "Synthesis of (Z)-N-Alkenylazoles and Pyrroloisoquinolines from -N-Azoleketones through Pd-Catalyzed Tosylhydrazone Cross-Couplings." Chemistry-a European Journal, 19(32), 10506-10510, 2013.
• Liu, C.L., C. Shi, F. Mao, Y. Xu, J.Y. Liu, B. Wei, J. Zhu, M.J. Xiang, and J. Li, "Discovery of New Imidazole Derivatives Containing the 2,4-Dienone Motif with Broad-Spectrum Antifungal and Antibacterial Activity." Molecules, 19(10), 15653-15672, 2014.
• Morris, D.J., A.M. Hayes, and M. Wills, "The "reverse-tethered" ruthenium (II) catalyst for asymmetric transfer hydrogenation: Further applications." Journal of Organic Chemistry, 71(18), 7035-7044, 2006.
• Porretta, G.C., R. Fioravanti, M. Biava, R. Cirilli, N. Simonetti, A. Villa, U. Bello, P. Faccendini, and B. Tita, "RESEARCH ON ANTIBACTERIAL AND ANTIFUNGAL AGENTS .10. SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF 1-PHENYL-2-(1H-AZOL-1-YL) ETHANE DERIVATIVES - ANTICONVULSANT ACTIVITY OF 1-(4-METHYLPHENYL)-2-(1H-IMIDAZOL-1-YL) ETHANOL." European Journal of Medicinal Chemistry, 28(10), 749-760, 1993.
• Przheval'skii, N.M., N.S. Skvortsova, and I.V. Magedov, "New derivatives of 3-aminoindole. Synthesis of 2-aryl(hetaryl)-3-(3,5-dimethyl-1-pyrazolyl)indoles." Khimiya Geterotsiklicheskikh Soedinenii, (11), 1662-1669, 2004.
• Rad, M.N.S., A. Khalafi-Nezhad, and S. Behrouz, "Design and Synthesis of Some Novel Oxiconazole-Like Carboacyclic Nucleoside Analogues, as Potential Chemotherapeutic Agents." Helvetica Chimica Acta, 92(9), 1760-1774, 2009.
• Rad, M.N.S., A. Khalafi-Nezhad, and S. Behrouz, "Synthesis of some novel hydrazono acyclic nucleoside analogues." Beilstein Journal of Organic Chemistry, 6, 2010.
• Rohrig, U.F., S.R. Majjigapu, M. Chambon, S. Bron, L. Pilotte, D. Colau, B.J. Van den Eynde, G. Turcatti, P. Vogel, V. Zoete, and O. Michielin, "Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors." European Journal of Medicinal Chemistry, 84, 284-301, 2014.
• Roman, G., J.Z. Vlahakis, D. Vukomanovic, K. Nakatsu, and W.A. Szarek, "Heme Oxygenase Inhibition by 1-Aryl-2-(1H-imidazol-1-yl/1H-1,2,4-triazol-1-yl)ethanones and Their Derivatives." Chemmedchem, 5(9), 1541-1555, 2010.
• Shah, K., B. Jandu, A. Abdullah, and S. Ahmed, "Synthesis, Biochemical Evaluation and Rationalisation of the Inhibitory Activity of a Range of Derivatives of 2-imidazol-1-yl-1-phenyl-ethanone as Potential Novel Inhibitors of 17 alpha-hydroxylase/17,20-lyase (P-450(17 alpha))." Letters in Drug Design & Discovery, 8(6), 516-522, 2011.
• Steiner, G., H. Kopacka, K.H. Ongania, K. Wurst, P. Preishuber-Pflugl, and B. Bildstein, "Heteroditopic imino N-heterocyclic carbenes and their sulfur, selenium, and tungsten tetracarbonyl derivatives." European Journal of Inorganic Chemistry, (7), 1325-1333, 2005.
• Wagman, A.S., R.S. Boyce, S.P. Brown, E. Fang, D. Goff, J.M. Jansen, V.P. Le, B.H. Levine, S.C. Ng, Z.I. Ni, J.M. Nuss, K.B. Pfister, S. Ramurthy, P.A. Renhowe, D.B. Ring, W. Shu, S. Subramanian, X.H.A. Zhou, C.M. Shafer, S.D. Harrison, K.W. Johnson, and D.E. Bussiere, "Synthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-lmidazol-2-yl-4-phenylpyrimidin-2-yl) 2-(2-pyridylamino)ethyl amine Inhibitors of Glycogen Synthase Kinase 3." Journal of Medicinal Chemistry, 60(20), 8482-8514, 2017.
• Zampieri, D., M.G. Mamolo, E. Laurini, G. Scialino, E. Banfi, and L. Vio, "Antifungal and antimycobacterial activity of 1-(3,5-diaryl-4,5dihydro-1H-pyrazol-4-yl)-1H-imidazole derivatives." Bioorganic & Medicinal Chemistry, 16(8), 4516-4522, 2008.
• Zampieri, D., M.G. Mamolo, E. Laurini, G. Scialino, E. Banfi, and L. Vio, "2-Aryl-3-(1H-Azol-1-yl)-1H-Indole Derivatives: A New Class of Antimycobacterial Compounds - Conventional Heating in Comparison with MW-Assisted Synthesis." Archiv Der Pharmazie, 342(12), 716-722, 2009.
• Friggeri, L., T.Y. Hargrove, G. Rachakonda, A.D. Williams, Z. Wawrzak, R. Di Santo, D. De Vita, M.R. Waterman, S. Tortorella, F. Villalta, and G.I. Lepesheva, "Structural Basis for Rational Design of Inhibitors Targeting Trypanosoma cruzi Sterol 14 alpha-Demethylase: Two Regions of the Enzyme Molecule Potentiate Its Inhibition." Journal of Medicinal Chemistry, 57(15), 6704-6717, 2014.
• Lakshmanan, B., P.M. Mazumder, D. Sasmal, and S. Ganguly, "Synthesis, antispasmodic and antidiarrheal activities of some 1-substituted imidazole derivatives." Acta Pharmaceutica, 61(2), 227-236, 2011.
• Yamada, K., O. Yajima, Y. Yoshizawa, and K. Oh, "Synthesis and biological evaluation of novel azole derivatives as selective potent inhibitors of brassinosteroid biosynthesis." Bioorganic & Medicinal Chemistry, 21(9), 2451-2461, 2013.
• Dulcevscaia, G.M., V.C. Kravtsov, F.Z. Macaev, G.G. Duca, E.P. Stingachi, S.I. Pogrebnoi, V.V. Boldescu, S.F. Clapco, J.P. Tiurina, A.A. Deseatnic-Ciloci, J. Lipkowski, S.X. Liu, S. Decurtins, and S.G. Baca, "New copper(II) complexes with isoconazole: Synthesis, structures and biological properties." Polyhedron, 52, 106-114, 2013.
• Mangas-Sanchez, J., E. Busto, V. Gotor-Fernandez, F. Malpartida, and V. Gotor, "Asymmetric Chemoenzymatic Synthesis of Miconazole and Econazole Enantiomers. The Importance of Chirality in Their Biological Evaluation." Journal of Organic Chemistry, 76(7), 2115-2122, 2011.
• Oh, K., Y. Shimura, K. Ishikawa, Y. Ito, T. Asami, N. Murofushi, and Y. Yoshizawa, "Asymmetric synthesis and stereochemical structure-activity relationship of (R)- and (S)-8- 1-(2,4-dichlorophenyl)-2-imidazol-1-yl-ethoxy octanoic acid heptyl ester, a potent inhibitor of allene oxide synthase." Bioorganic & Medicinal Chemistry, 16(3), 1090-1095, 2008.
• Bennett, G.A., G.B. Mullen, J.T. Mitchell, W.E. Jones, S.D. Allen, C.R. Kinsolving, and V. Stgeorgiev, "STUDIES ON ANTIFUNGAL AGENTS .30. - NOVEL SUBSTITUTED 3-(2-FURANYL)-3-(1H-IMIDAZOL-1-YLMETHYL)-2-METHYL-5-PHENYL (OR PHENYLOXYMETHYL) ISOXAZOLIDINES." European Journal of Medicinal Chemistry, 24(6), 579-583, 1989.
• Frisch, M.J., G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. Montgomery, J. A. , J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox, Gaussian 09. 2013, Gaussian Inc.: Wallingford CT.
• Dennington, R., T. Keith, and J. Millam, GaussView, Version 5. 2009, Semichem Inc.: Shawnee Mission, KS.
• Hanwell, M.D., D.E. Curtis, D.C. Lonie, T. Vandermeersch, E. Zurek, and G.R. Hutchison, "Avogadro: an advanced semantic chemical editor, visualization, and analysis platform." Journal of Cheminformatics, 4(1), 17, 2012.
• Chattaraj, P.K., U. Sarkar, and D.R. Roy, "Electrophilicity index." Chemical Reviews, 106(6), 2065-2091, 2006.
• Koopmans, T., "Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms." Physica, 1(1), 104-113, 1934.
• Makov, G., "Chemical Hardness in Density Functional Theory." The Journal of Physical Chemistry, 99(23), 9337-9339, 1995.
• Mulliken, R.S., "A New Electroaffinity Scale; Together with Data on Valence States and on Valence Ionization Potentials and Electron Affinities." J. Chem. Phys., 2, 782, 1934.
• Parr, R.G. and R.G. Pearson, "Absolute Hardness-Companion Parameter to Absolute Electronegativity." Journal of the American Chemical Society, 105(26), 7512-7516, 1983.
• Parr, R.G., L. Von Szentpaly, and S.B. Liu, "Electrophilicity index." Journal of the American Chemical Society, 121(9), 1922-1924, 1999.
• Pearson, R.G., "Hard and Soft Acids and Bases." Journal of the American Chemical Society, 85(22), 3533-&, 1963.
• Pearson, R.G., "Hard and Soft Acids and Bases HSAB.1.Fundamental Principles." Journal of Chemical Education, 45(9), 581-&, 1968.
• Pearson, R.G., "Maximum chemical and physical hardness." Journal of Chemical Education, 76(2), 267-275, 1999.
• Erdogan, T., "The First Synthesis of Some Novel 4‐Chloro Chalcone Based Oxime Ethers: An Experimental and Computational Study." Süleyman Demirel University Journal of Natural and Applied Sciences, 20(3), 475-489, 2016.
• Erdogan, T. and F.O. Erdogan, "An Improved, Efficient and Microwave Assisted Synthetic Method for the Synthesis of Chalcone Oximes: An Experimental and Computational Study." Letters in Organic Chemistry, 15(2), 99-110, 2018.