Structural and quantum chemical studies on aryl sulfonyl piperazine derivatives
The optimized molecular structure and electronic features of aryl sulfonyl piperazine derivatives 1-4 have been investigated theoretically using Gaussian 09 software package and DFT/B3LYP method with 6-31G (d,p) basis set. The reactivity of the title molecules was investigated and both the positive and negative centers of the molecules were identiﬁed using molecular electrostatic potential (MEP) analysis which the results illustrate that the regions reveal the negative electrostatic potential are localized in sulfamide function while the regions presenting the positive potential are localized in the hydrogen atoms. The energies of the frontier molecular orbitals and LUMO-HOMO energy gap are measured to explain the electronic transitions. Global reactivity parameters of the aryl sulfonyl piperazine derivatives molecules were predicted to find that the more reactive and softest compound is the compound 3. Mulliken’s net charges have been calculated and results show that 3N is the more negative and 33S is the more positive charge, which Indicates extensive charge delocalization in the entire molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization (π→π transitions) has been analyzed using NBO analysis. Fist hyperpolarizability is calculated in order to ﬁnd its importance in non-linear optics and the results show that the studied molecules have not the NLO applications.
Keywords: sulfamide; density functional theory; computational chemistry; electronic structure; quantum chemical calculations.
2. Drew J, Drug discovery: a historical perspective, Science, 2000; 287:1960-1964.
3. Owa T, Nagasu T, Novel sulphonamide derivatives for the treatment of cancer, Exp Opin Ther Patents 2000; 10(11):1725-1740. https://doi.org/10.1517/135437184.108.40.2065.
4. Supuran CT, Scozzafava A, Carbonic anhydrase inhibitors and their therapeutic potential. Exp. Opin. Ther. Patents, 2000; 10(5):575-600. https://doi.org/10.1517/135437220.127.116.115.
5. Supuran CT, Scozzafava A, Carbonic Anhydrase Inhibitors Curr Med Chem-Imm., Endoc. Metab. Agents, 2001; 1(1):61-97. https://doi.org/10.2174/1568013013359131.
6. Maren TH, Relations Between Structure and Biological Activity of Sulfonamides. Annu Rev Pharmacol Toxicol, 1976; 16:309-327. https://doi.org/10.1146/annurev.pa.16.040176.001521.
7. Boyd AE, Sulfonylurea Receptors, Ion Channels, and Fruit Flies, Diabetes, 1988; 37(7):847-850. https://doi.org/10.2337/diab.37.7.847.
8. Thornber CW, Isosterism and molecular modification in drug design, Chem. Soc. Rev, 1979; 8(4):563-580. Available: https://doi.org/10.1039/CS9790800563.
9. Ogden RC, Flexner CW, Protease Inhibitors in AIDS Therapy, New York, U.S.A: Marcel Dekker; 2001.
10. Supuran CT, Scozzafava A, Mastrolorenzo A, Bacterial proteases: current therapeutic use and future prospects for the development of new antibiotics, Exp. Opin. Therap. Patents, 2001; 11(2):221-259. https://doi.org/10.1517/13543718.104.22.168.
11. Scozzafava A, Supuran CT, Carbonic Anhydrase and Matrix Metalloproteinase Inhibitors: Sulfonylated Amino Acid Hydroxamates with MMP Inhibitory Properties Act as Efficient Inhibitors of CA Isozymes I, II, and IV, and N-Hydroxysulfonamides Inhibit Both These Zinc Enzymes, J. Med. Chem, 2000; 43(20):3677-3687. https://doi.org/10.1021/jm000027t.
12. Parr RG, Yang W, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
13. Srivastava AK, Pandey AK, Jain S, Misra N, FT-IR spectroscopy, intra-molecular C−H⋯O interactions, HOMO, LUMO, MESP analysis and biological activity of two natural products, triclisine and rufescine: DFT and QTAIM approaches, Spectrochim. Acta A, 2015; 136:682-689. https://doi.org/10.1016/j.saa.2014.09.082.
14. Narendra Sharath Chandra JN, Sadashiva CT, Kavitha CV, Rangappa KS, Synthesis and in vitro antimicrobial studies of medicinally important novel N-alkyl and N-sulfonyl derivatives of 1-[bis(4-ﬂuorophenyl)-methyl]piperazine, Bioorg. Med. Chem, 2006; 14(19):6621-6627. https://doi.org/10.1016/j.bmc.2006.05.064.
15. Dennington R, Keith T, Millam J, Gaussview, Version 5, Semichem. Inc.,Shawnee Missions, KS, 2009.
16. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al, Gaussian 09, Revision C.01; Gaussian Inc.: Wallingford, CT, USA, 2010.
17. Becke AD. Density‐functional thermochemistry. III. The role of exact exchange, J. Chem. Phys, 1998; 1998(7): 5648-5652. https://doi.org/10.1063/1.464913.
18. Gunasekaran S, Balaji RA, Kumeresan S, Anand G, Srinivasan S. Can, Experimental and theoretical investigations of spectroscopic properties of N-acetyl-5-methoxytryptamine, J. Anal. Sci. Spectrosc, 2008; 53:149-160.
19. Kavitha E, Sundaraganesan N, Sebastian S, Molecular structure, vibrational spectroscopic and HOMO, LUMO studies of 4-nitroaniline by density functional method, Ind. J. Pure Appl. Phys. 2010; 48:20-30.
20. Geerlings P, Proft FD, Langenaeker W, Conceptual Density Functional Theory, Chem. Rev. 2003; 103(5):1793-1873. https://doi.org/10.1021/cr990029p.
21. Jug K, Maksic ZB, in: Z.B. Maksic (Ed.), Theoretical Model of Chemical Bonding, Part 3, Springer, Berlin, 1991, p. 233.
22. Xiao-Hong L, et al, Calculation of vibrational spectroscopic and NMR parameters of 2-Dicyanovinyl-5-(4-N,N-dimethylaminophenyl) thiophene by ab initio HF and density functional methods, Comput. Theor. Chem, 2011; 969(1-3):27-34. https://doi.org/10.1016/j.comptc.2011.05.010.
23. Bailey RT, Dines TJ, Tedford MC, Electron-phonon coupling in the molecular charge transfer crystal 2-(α-methylbenzylamino)-5-nitropyridine, J. Mol. Struct, 2011; 992(1-3):52-58. https://doi.org/10.1016/j.molstruc.2011.02.035.
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License. that allows others to share the work with an acknowledgment of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgment of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (SeeÂ The Effect of Open Access).