The theoretical investigation of solvent effects on the relative stability and 15N NMR shielding of antidepressant heterocyclic drug

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• 作者：Arezoo Tahan ; Mahya Khojandi ; Ali Akbar Salari
• 关键词：heterocyclic drug ; mirtazapine ; PCM model ; NMR tensors ; NBO analysis
• 刊名：Russian Journal of Physical Chemistry A, Focus on Chemistry
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：90
• 期：1
• 页码：130-135
• 全文大小：260 KB
• 参考文献：1.P. M. Hartmann, Am. Fam. Phys. 59, 159 (1999).
  2.T. de Boer, J. Clin. Psychiatry 57 (Suppl. 4), 19 (1996).
  3.S. A. Anttila and E. V. Leinonen, CNS Drug Rev. 7, 249 (2001).CrossRef
  4.T. de Boer, F. Nefkens, and A. van Helvoirt, Eur. J. Pharmacol. 253, R5 (1994).CrossRef
  5.T. de Boer, G. Maura, M. Raiteri, C. de Vos, J. Wieringa, and R. Pinder, Neuropharmacol. 27, 399 (1988).CrossRef
  6.K. J. Holm and A. Markham, Drugs 57, 607 (1999).CrossRef
  7.G. S. Ruigt, B. Kemp, C. M. Groenhout, and H. A. Kamphuisen, Eur. J. Clin. Pharmacol. 38, 551 (1990).CrossRef
  8.G. L. Stimmel, J. A. Dopheide, and S. M. Stahl, Pharmacotheraphy 17, 10 (1997).
  9.P. Jolliet, G. Veyrac, and M. Bourin, Eur. Psychiatry 16, 503 (2001).CrossRef
  10.T. Romiguieres, F. Pehourcq, M. Matoga, B. Begaud, and C. Jarry, J. Chromatogr. B 775, 163 (2002).CrossRef
  11.S. Dodd, G. D. Burrows, and T. R. Norman, J. Chromatogr. B 748, 439 (2000).CrossRef
  12.U. Selditz, Y. Liao, J. P. Franke, R. A. de Zeeuw, and H. Wikstr枚m, J. Chromatogr. A 803, 169 (1998).CrossRef
  13.C. Kirkton and I. M. McIntyre, J. Anal. Toxicol. 30, 687 (2006).CrossRef
  14.J. E. Paanakker and H. J. M. van Hal, J. Chromatogr. Biomed. Appl. 417, 203 (1987).CrossRef
  15.I. Meineke, I. Kress, W. Poser, E. R眉ther, and J. Brockm枚ller, Ther. Drug. Monit. 26, 277 (2004).CrossRef
  16.N. Karasen and S. Altin枚z, J. Pharm Biomed. Anal. 24, 11 (2000).CrossRef
  17.P. M. Bhatt, N. V. Ravindra, R. Banerjee, and G. R. Desiraju, Chem. Commun. 8, 1073 (2005).CrossRef
  18.E. Iishi and Y. Imamiya, US Patent No. 6723845 B2, EP 1225174 B1 (2007).
  19.B. Sarma, R. Thakuria, N. K. Nath, and A. Nangia, Cryst. Eng. Commun. 13, 3232 (2011).CrossRef
  20.J. Kelder, C. Funke, T. de Boer, L. Delbressine, D. Leysen, and V. Nickolson, J. Pharm. Pharmacol. 49, 403 (1997).CrossRef
  21.S. G. Sagdinc and A. E. Sahinturk, J. Mol. Struct. 1021, 53 (2012).CrossRef
  22.S. G. Sagdinc and A. E. Sahinturk, Spectrochim. Acta A: Mol. Biomol. Spectrosc. 104, 222 (2013).CrossRef
  23.H. Demirhan, M. Arslan, M. Zengin, and M. Kucukislamoglu, J. Spectrosc. 2013, 1 (2013).CrossRef
  24.C. W. Funke, Recl. Trav. Chim. Pays-Bas 101, 437 (1982).CrossRef
  25.B. Chankvetadze, G. Endresz, D. Bergenthal, and G. Blaschke, J. Chromatogr. A 717, 245 (1995).CrossRef
  26.A. A. Salari, M. Talebi Tari, M. Noei, and A. Tahan, Arab. J. Chem., Available online August 27, 2013 (in press).
  27.A. Tahan and N. Ahmadinejad, J. Struct. Chem. 55, C877 (2014).CrossRef
  28.J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian, and M. J. Frisch, J. Phys. Chem. 100, 16098 (1996).CrossRef
  29.E. D. Glendening, A. E. Reed, J. E. Carpenter, and F. Reinhold, NBO, Version 3.1 (1998).
  30.A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev. 88, 899 (1988).CrossRef
  31.R. Cammi, B. Mennucci, and B. Tomasi, J. Chem. Phys. 110, 7627 (1999).CrossRef
  32.M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgometry, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Milliam, S. S. Iyengar, J. Jomasi, V. Barone, B. Mennucci, et al., Gaussian 03, Revision A.1 (Gaussian Inc., Pittsburgh, PA, 2003).
  
• 作者单位：Arezoo Tahan (1)
  Mahya Khojandi (1)
  Ali Akbar Salari (1)
  
  1. Semnan Branch, Islamic Azad University, Semnan, Iran
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Physical Chemistry
  Russian Library of Science
  
• 出版者：MAIK Nauka/Interperiodica distributed exclusively by Springer Science+Business Media LLC.
• ISSN：1531-863X

文摘

The density functional theory (DFT) and Tomasi鈥檚 polarized continuum model (PCM) were used for the investigation of solvent polarity and its dielectric constant effects on the relative stability and NMR shielding tensors of antidepressant mirtazapine (MIR). The obtained results indicated that the relative stability in the polar solvents is higher than that in non-polar solvents and the most stable structure was observed in the water at the B3LYP/6-311++G (d,p) level of theory. Also, natural bond orbital (NBO) interpretation demonstrated that by increase of solvent dielectric constant, negative charge on nitrogen atoms of heterocycles and resonance energy for LP(N₁₀) 鈫?蟽* and 蟺* delocalization of the structure鈥檚 azepine ring increase and the highest values of them were observed in water. On the other hand, NMR calculations showed that with an increase in negative charge of nitrogen atoms, isotropic chemical shielding (蟽_iso) around them increase and nitrogen of piperazine ring (N₁₉) has the highest values of negative charge and 蟽_iso among nitrogen atoms. NMR calculations also represented that direct solvent effect on nitrogen of pyridine ring (N₁₅) is more than other nitrogens, while its effect on N₁₉ is less than other ones. Based on NMR data and NBO interpretation, it can be deduced that with a decrease in the negative charge on nitrogen atoms, the intramolecular effects on them decrease, while direct solvent effect increases. Keywords heterocyclic drug mirtazapine PCM model NMR tensors NBO analysis