Quantum Chemical Analysis of Structural and Conformational Properties of Methisazone and Prototropic Tautomerism of Isatin
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The conformational diversity of methisazone and prototropic molecular tautomerism of isatin were investigated by means of ab initio calculations at the MP2/6-311++G(2df,pd)//DFT B3LYP/6-311++G(d,p) level of theory. A comprehensive conformational, energetical and polar analysis of the methisazone (1-methyl-1H-indole-2,3-dione 3-thiosemicarbazone), a thiosemicarbazone, was provided. We established that flexibility of the thiosemicarbazone group causes conformational diversity of methisazone molecule. Structural, energetical and electron-topological characteristics of specific intramolecular contacts in methisazone conformers were analyzed. In general, two types of H-bonds (NH…O, CH…N), one type of dihydrogen bond (CH…HN) and three types of van der Waals contacts (N…N, N…O, C…O) were detected by performing electron density topological analysis for all 11 conformers of methisazone. A wide range of biological activity of izatizon based on conformational capacity of methisazone molecule, the main constituent part of this drug, was shortly discussed. Five molecular prototropic tautomers of isatin (1H-indole-2,3-dione) – one diketo and four enol tautomeric forms - were indicated. All five isomers have relative Gibbs free energies within a wide range of ~40 kcal∙mol−1 at physiological temperature. The possible biochemical role of tautomeric forms of isatin was briefly discussed
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L.A. Zaika, O.I. Bolsunova, A.I. Potopalsky, Antiviral, Antitumor and Immunomodulatory Properties of Izatizon Drug (Kolobih, 2010).
A.I. Potopalsky, L.V. Lozyuk, Izatizon is an Antiviral and Antitumor Drug (Naukova Dumka, 1995).
D.J. Bauer, L. St. Vincent, et al., Prophylaxis of Smallpox with Methisazone, American Journal of Epidemiology, Volume 90, (Issue 2), August 1969, pp. 130-145.
C.G. Heiner, N. Fatima, et al., Field Trial of Methisazone as a Prophylactic Agent Against Smallpox, American Journal of Epidemiology, Volume 94, (Issue 5), November 1971, pp. 435-449.
L.A. do Valle, P.R. de Melo et al., Methisazone in Prevention of Variola Minor Among Contacts, Lancet, Volume 2, (Issue 7420), November 1965, pp. 976-978.
J.C. Deavin, D.H. Mitchell, The Analysis Of Methisazone, Journal of Pharmacy and Pharmacology, Volume 17, (Issue S1), December 1965, pp. 56S–59S.
A.L. Potyahaylo, O.I. Bolsunova et al., Conformational Analysis of Metysazon Molecule: the Results of Semi-Empirical Quantum-Chemical Calculations, Biopolymers and Cell, Volume 19, (Issue 3), May-June 2003, pp. 292 -294.
A.L. Potyahaylo, O.I. Bolsunova et al., Prototropic Tautomerism and Proton-Donor - Proton-Acceptor Properties of Isatin According to the Semiempirical Quantum-Chemical Calculations, Biopolymers and Cell, Volume 19, (Issue 2), March-April 2003, pp. 202 -204.
O.O. Brovarets’, D.M. Hovorun How Stable are the Mutagenic Tautomers of DNA Bases? Biopolymers and Cell, Volume 26, (Issue 1), January-February 2010, pp. 72 – 76.
O.O. Brovarets’, D.M. Hovorun Intramolecular Tautomerization and the Conformational Variability of Some Classical Mutagens – Cytosine Derivatives: Quantum Chemical Study, Biopolymers and Cell, Volume 27, (Issue 3), May-June 2011, pp. 221-230.
J. Tirado-Rives, W.L. Jorgensen, Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules, Journal of Chemical Theory and Computation, Volume 4, (Issue 2), January 2008, pp. 297-306.
A. Muller, M. Losada et al., Ab Initio Benchmark Study of (2-Pyridone)2, a Strongly Bound Doubly Hydrogen-Bonded Dimer, Journal of Physical Chemistry A, Volume 108, (Issue 1), November 2004, pp. 157–165.
J. Gu, J. Leszczynski, A DFT Study of the Water-Assisted Intramolecular Proton Transfer in the Tautomers of Adenine, Journal of Physical Chemistry A, Volume 103, (Issue 15), March 1999, pp. 2744–2750.
A.M. Mebel, K. Morokuma, et al., Modification of the GAUSSIAN-2 Theoretical Model: The Use of Coupled-Cluster Energies, Density-Functional Geometries, and Frequencies, Journal of Chemical Physics, Volume 103, (Issue 17), November 1995, pp. 7414–7421.
M.J. Frisch, M. Head-Gordon, et al., Semi-Direct Algorithms for the MP2 Energy and Gradient, Chemical Physics Letters, Volume 166, (Issue 3), February 1990, pp. 281-289.
Gaussian 03, Revision С. 02, Frisch M. J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., 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., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J. J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J. B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A./Gaussian, Inc., Wallingford CT, 2004.
R.W.F. Bader, Atoms in Molecules. A Quantum Theory (Clarendon Press, 1990).
AIMAll (Version 10.07.01), Keith, T.A., 2010 (aim.tkgristmill.com).
E. Espinosa, E. Molins, et al., Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities, Chemical Physics Letters, Volume 285, (Issues 3-4), March 1998, pp. 170-173.
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