Cocsuline, a biologically active natural product, is biosynthetically related to the more common bisbenzylisoquinoline alkaloids. We perform a comprehensive quantum chemical analysis on cocsuline using density functional theory at B3LYP/6-311G(d,p) level. The equilibrium molecular structure of cocsuline has been obtained. The weak intra-molecular C-H…O interaction is recognized, characterized and quantified by quantum theory of atoms in molecule (QTAIM). The chemical reactivity of cocsuline is explained and discussed with the help of HOMO, LUMO and MESP surfaces. The vibrational infrared spectrum of cocsuline has been calculated and prominent vibrational modes have been assigned. A good agreement between our calculated wavenumbers and experimentally reported values has been observed. The molecular docking of cocsuline into dihydrofolate reductase receptor shows that it may inhibits this enzyme and acts as an effective antimalarial drug.
SrivastavaA.K. and MisraN., A comparative theoretical study on the biological activity, chemical reactivity, and coordination ability of dichloro-substituted (1,3-thiazol-2-yl) acetamides, Can J Chem92 (2014), 234–239.
9.
SrivastavaA.K., BabooV., NarayanaB., SarojiniB.K. and MisraN., Comparative DFT study on reactivity and vibrational spectra of halogen substituted phenylacetic acids, Indian J Pure & Appl Phys52 (2014), 507–519.
10.
SrivastavaA.K., NarayanaB., SarojiniB.K. and MisraN., Vibrational, structural and hydrogen bonding analysis of N’-[(E)-4-Hydroxybenzylidene]-2-(naphthalene-2-yloxy) acetohydrazide: Combined density functional and atoms-in-molecule based theoretical studies, Indian J Phys88 (2014), 547–556.
11.
SrivastavaA.K., PandeyA.K., GangwarS.K. and MisraN., Structural, vibrational and electronic properties of cis and trans conformers of 4-hydroxy-l-proline: A density functional approach, J At Mol Sci5 (2014), 279–288.
12.
DwivediA., SrivastavaA.K. and BajpaiA., Vibrational spectra, HOMO, LUMO, MESP sufaces and reactivity descriptors of amylamine and its isomers: A DFT study, Spectrochim Acta A149 (2015), 343–351.
13.
SrivastavaA.K., PandeyA.K., JainS. and MisraN., FT-IR spectroscopy, intra-molecular C-H—O interactions, HOMO, LUMO, MESP analysis and biological activity of two natural products, triclisine and rufescine: FT and QTAIM approaches, Spectrochim Acta A136 (2015), 682–689.
14.
KumarA., SrivastavaA.K., GangwarS., MisraN., MondalA. and BrahmachariG., Combined experimental (FT-IR, UV-visible spectra, NMR) and theoretical studies on the molecular structure, vibrational spectra, HOMO, LUMO, MESP suefaces, reactivity descriptor and molecular docking of Phomarin, J Mol Struct1096 (2015), 94–101.
15.
BaderR.F.W., Atoms in Molecules. A Quantum Theory (New York: oxford) 2nd ed. (1990).
16.
DenningtonR., KeithT. and MillamJ., GaussView Version 5.0, Semichem Inc. KS (2005).
17.
BeckeA.D., Density functional thermochemistry.III. The role of exact exchange, J Chem, Phys98 (1993), 5648.
18.
LeeC., YangW. and ParrR.G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys Rev B1337 (1988), 785.
19.
MerrickJ.P., MoranD. and RadomL., An Evaluation of Harmonic vibration frequency scale factors, J Phys Chem A111 (2007), 11683–11700.
KeithT.A., AIMAll Version 12.09.23, TK Gristmill Software, Overland Park KS USA, (2012).
22.
RozasI., AlkortaI. and ElgueroJ., Behavior of Ylides containing N, O and C atoms as Hydrogen bond Acceptors, J Am Chem Soc122 (2000), 11154.
23.
EspinosaE., MolinsE. and LecomteC., Hydrogen bond strength revealed by topological analyses of experimentally observed electron densities, Chem Phys Lett285 (1998), 170.
24.
GeorgeS., Infrared and Raman characteristic group frequencies-Tables and Charts, Third ed., Wiley, Chichester, (2001).
25.
ArjunanV., Sakila deviS.,
MarchewkaM.K.,
MohanS.,
FT-IR and FT-Raman, FT-NMR and quantum chemical investigations of 3-acetylcoumarin, Spectrochim Acta A109 (2013), 79.
26.
ManolopoulosD.E., MayJ.C. and DownS.E., Systematic relationships between fullerenes without spirals, Chem Phys Lett181 (1991), 105.
27.
LuqulF.J., LopezJ.M. and OrozcoM., Perspective on “Electrostatic interactions of a solute with a continuum, A direct utilization of ab initio molecular potentials for the prevision of solvent effects”, Theor Chem Acc103 (2000), 343.
28.
ScroccoE. and TomasiJ., The electrostatic molecular potential as a tool for the interpretation of molecular properties, Top Curr Chem42 (1973), 95.
29.
SrivastavaV., KumarA., MishraB.N. and SiddiquiM.I., Molecular docking studies on DMDP derivatives as human DHFR inhibitors, Bioinformation4 (2008), 180–188.
