Abstract

Structure based biological and chemical properties of 4-(carboxyamino)-benzoic acid has been studied by quantum chemical methods. The revamped geometric structure and its quantum chemical parameters were obtained by DFT-B3LYP/6-311G method. Normal mode analysis is performed to assign the fundamental vibrational frequencies as per the potential energy distribution (PED) by using the VEDA program. Simulation of IR and Raman spectral patterns are observed by refinement of scale factors. TD-DFT approach is used to explore the excited states of molecule and prediction of electronic absorption spectra. NMR chemical shifts of the molecule are determined by the gauge independent atomic orbital method. The molecular docking is performed to recognize the binding energy of the ligand with the dynamic site of protein. In our docking analysis, the protein 5DT6 shows the best results than other three proteins which could be used for further analysis. Further inter and intra molecular interactions, electrophilic, nucleophilic and chemical reactivity sites are found by molecular electrostatic potential, HOMO-LUMO and Global chemical reactivity descriptors. Thermodynamic property of the title compound is also reported. The determined quantum chemical parameters show high reactivity and the dipole moment was sufficiently high enough to induce nonlinear characteristics which are required for applications in optoelectronic devices.

Keywords: DFT; HOMO; LUMO; MEP; FMO; RDG; ADMET

References

1. Chang Te-Yang and Miao-Lin Hu. "Concentrations And Lipid Peroxidation In Tissues And Toxicity Of Para-Aminobenzoic Acid Fed To Rats In Drinking Water". The Journal of Nutritional Biochemistry7 (1996): 408-413. 
2. Basset GJC., et al. "Folate Synthesis In Plants: The P-Aminobenzoate Branch Is Initiated By A Bifunctional Paba-Pabb Protein That Is Targeted To Plastids". Proceedings of the National Academy of Sciences6 (2004): 1496-1501. 
3. Pierrel Fabien., et al. "Involvement Of Mitochondrial Ferredoxin And Para-Aminobenzoic Acid In Yeast Coenzyme Q Biosynthesis". Chemistry and Biology5 (2010): 449-459. 
4. Marbois Beth., et al. "Para-Aminobenzoic Acid Is A Precursor In Coenzyme Q6 Biosynthesis In Saccharomyces Cerevisiae". Journal Of Biological Chemistry36 (2010): 27827-27838. 
5. Kostic N., et al. “Diagnostic value of the NBT-PABA test in the functional evaluation of the exocrine pancreas”. Srp Arb Celok Lek 120 (1992): 269-272.
6. Song Geun Cheol., et al. "The Folate Precursor Para-Aminobenzoic Acid Elicits Induced Resistance Against Cucumber Mosaic Virus And Xanthomonas Axonopodis". Annals of Botany5 (2013): 925-934. 
7. Zajkov Gennady E., et al.Progress In Organic And Physical Chemistry. Apple Academic Press (2013).
8. Short James H., et al. "Sympathetic Nervous System Blocking Agents. V. Derivatives Of Isobutyl-, Tert-Butyl-, And Neopentylguanidine". Journal Of Medicinal Chemistry6 (1968): 1129-1135. 
9. Alcolea Palafox M., et al. “Theoretical Quantum Chemical Study Of Benzoic Acid: Geometrical Parameters And Vibrational Wavenumbers”. International Journal of Quantum Chemistry1 (2002): 1-24.
10. Wang B and Ma H Z. “Chiroptical Lanthanide (III) schiff base complexes derived from p-Nitrophenyl-hydrazine and D-Camphor-β-sulphonic acid”. Inorganic Chemistry Communications5 (2001): 248-251.
11. Muthu S and J Uma Maheswari. “Quantum mechanical study and spectroscopic (FT-IR, FT-Raman, 13C, 1H, UV) study, first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis of 4-[ (4-aminobenzene) sulfonyl] aniline by ab initio HF and density functional method”. Spectrochimica acta. Part A, Molecular and Biomolecular Spectroscopy 92 (2012): 154-163.
12. Bunce S J., et al. “Synthetic Polyisoprenes Studied By Fourier Transform Raman Spectrocopy”. Spectrochimica Acta Part A: Molecular Spectroscopy 49 (1993): 775-783.
13. Varsanyi G. “Vibrational Spectra of Benzene Derivatives”. New York: Academic Press (1969).
14. Kowalczyk I. “Spectroscopic Studies, Molecular Structure And Hydrogen Bonding In Hydrates Of Gemini Betaines”. Journal of Molecular Structure 973 (2010): 163-172.
15. Machida K., et al. “Vibrational Spectra And Intermolecular Potential Of The α-form Crystal Of Glycine”. Spectrochimica Acta Part A: Molecular Spectroscopy5 (1977): 569-574.
16. Sathyanarayana DN. “Vibrational Spectroscopy Theory and Applications”. 2nd ed., New Delhi, Age International (P) Limited Publishers (2004).
17. Ramkumaar Govindaswamy Ranganathan., et al. “Molecular Structure, Vibrational Spectra, UV-VIS, NBO, And NMR Analysis On Nevirapine Using AB Initio Methods”. Journal of Theoretical and Applied Physics 7 (2013): 1-14.
18. Renuga S., et al. “FTIR And Raman Spectra, Electronic Spectra And Normal Coordinate Analysis Of N,N-dimethyl-3-phenyl-3-pyridin-2-yl-propan-1-amine By DFT Method”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 127 (2014): 439-453.
19. Halil Gökce and Semiha Bahçeli. “A Study Of Molecular Structure And Vibrational Spectra Of Copper (II)halide Complex Of 2- (2’-thienyl)pyridine”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012): 139-147.
20. Saravanamoorthy S N. “Computational Analysis And Molecular Docking Study Of 4- (carbodyamino)-3-guanidino-benzoic acid”. Advanced Journal of Chemistry-Section B2 (2021): 120-147.
21. Sundaraganesan N. “Molecular Structure And Vibrational Spectra Of 3-chloro-4-fluoro benzonitrile by ab initio HF And Density Functional Method”. Spectrochimca Acta Part A: Molecular and Bimolecular Spectroscopy3 (2008): 1134-1139.
22. Govindasamy P., et al. “Molecular Geometry, Conformational, Vibrational Spectroscopic, Molecular Orbital And Mulliken Charge Analysis Of 2-acetoxybenzoic Acid”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 130 (2014): 329-336.
23. Agarwal P., et al. “Density Functional Theory Studies On The Structure, Spectra (FT-IR, FT-Raman, And UV) And First Order Molecular Hyperpolarizability Of 2-hydroxy-3-methoxy-N- (2-chloro-benzyl)-benzaldehyde-imine: Comparison To Experimental Data”. Vibrational Spectroscopy 64 (2013): 134-147.
24. 24.   Andrea Alparone. “Second Harmonic Generation, Electrooptical Pockels Effect, And Static First-Order Hyperpolarizabilities Of 2,2’-Bithiophene Conformers: An HF, MP2, and DFT Theoretical Investigation”. Advances in Physical Chemistry 2013 (2013): 1-8.
25. 25.   Anuj Kumar., et al. “Computational Studies Of Third-Order Nonlinear Optical Properties Of Pyridine Derivative 2-aminopyridinium p-toluenesulphonate crystal”. Pramana-Journal of Physics 89 (2017): 7.
26. Jan Fleming. Frontier Orbitals and Organic Chemical Reactions, John Wiley and Sons, New York 320.5 (1978): 879-880.
27. Parr RG and Pearson RG. “Absolute Hardness: Companion Parameter To Absolute Electronegativity”. Journal of the American Chemical Society26 (1983): 7512-7516.
28. Parr R G and Yang W. Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York 47.1 (1989): 101.
29. Ersin Inkaya. “Synthesis, X-ray Structure, FT-IR, NMR, UV-Vis Spectroscopy, TG/DTA Study And DFT Calculations On 2- (benzo[d]thiazol-2-ylthio)-1- ( (1s, 3s)-3-mesityl-3-methylcyclobutyl ethan-1-one”. Journal of Molecular Structure 1173 (2018): 148-156.
30. Bakkiyaraj D., et al. “Spectroscopic (FT-IR, FT-Raman, FT-NMR And UV-Vis) investigation on benzyl dioxime Using Quantum Computational methods”. Journal of Molecular Structure 1108 (2016): 33-45.
31. 31.   Arshad MN., et al. “Synthesis, Crystal Structures and Spectroscopic Properties Of Triazine-Based Hydrazone Derivatives; A Comparative Experimental-Theoretical Study”. Molecules 20 (2015): 5851-5874.
32. Rajalakshmi K., et al. “Density Functional Theory, Comparative Vibrational Spectroscopic Studies, Highest Occupied Molecular Orbital And Lowest Unoccupied Molecular Orbital Analysis Of Linezolid”. Indian Journal of Physics 89 (2015): 525-538.
33. Reed A E., et al. “Natural Population Analysis”. The Journal of Chemical Physics 83 (1985): 735-746.
34. Govindarajan M and Karabacak M. “Spectroscopic Properties, NLO, HOMO-LUMO and NBO Analysis Of 2.5-Lutidine”. Spectrochimca Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012): 421-435.
35. Yadav T., et al. “Molecular Modelling And Spectroscopic Investigation Of A Neurotransmitter: Epinephrine”. Journal of Molecular Structure 1176 (2019): 94-109.
36. Sevvanthi S., et al. “Molecular Docking, Vibrational Spectroscopy Studies Of (RS)-2- (tert-butylamino)-1- (3-chlorophenyl)propane-1-one: A Potential Adrenaline Uptake Inhibitor”. Journal of Molecular Structure 1173 (2018): 251-260.
37. Veeraragavan Vijayakumar., et al. “Synthesis, Characterization, Spectroscopic Studies, DFT And Molecular Docking Analysis of N⁴, N⁴’-dibutyle-3-3’-diaminobenzidine”. Journal of Molecular Structure 1179, 2019): 325-335.
38. Noureddine O., et al. “Quantum Chemical Studies On Molecular Structure, AIM, ELF, RDG and Antiviral Activities Of Hybrid Hydroxychloroquine In The Treatment Of COVID-19: Molecular Docking And DFT Calculations”. Journal of Kind Saud University - Science2 (2021): 101334.
39. Schlick T. “Molecular Modeling and Simulation: An Interdisciplinary Guide”. 2nd ed. Springer, New York, 2010): 20 and 243.
40. Marinescu M. “Structural Studies And Optical Nonlinear Response Of Some Pyrazole-5-ones”. Nanoscience and Nanotechnology Letters 7 (2015): 1-9.
41. Wazzan N and Safi Z. “DFT Calculations Of The Tautomerization And NLO Properties Of 5-amino-7- (pyrrolidine-1-yl)-2,4,4-trimethyl-1,4-dihydro-1,6-naphthyridine-8-carbonitrile (APNC)”. Journal of Molecular Structure 1143 (2017): 397-404.
42. Lipinski CA., et al. “Experimental And Computational Approaches To Estimate Solubility And Permeability In Drug Discovery And Development Settings”. Advanced Drug Delivery Reviews1-3 (1997): 3-25.
43. Govindammal M and Prasath M. “Vibrational Spectra, Hirschfield Surface Analysis, Molecular Docking Studies Of (RS)-N,N-bis (2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide by DFT Approach”. Heliyon8 (2020): e04641.
44. Singh S and Singh J. “Transdermal Drug Delivery By Passive Diffusion And Iontophoresis: A Review”. Medicinal Research Reviews 13 (1993): 569-621.
45. Zhao YH., et al. “Evaluation Of Human Intestinal Absorption Data And Subsequent Derivation Of A Quantitative Structure-Activity Relationship (QSAR) With The Abraham Descriptors”. Journal of Pharmaceutical Sciences 90 (2001): 749-784.
46. Alavijeh MS., et al. “Drug metabolism And Pharmacokinetics, The Blood-Brain Barrier, And Central Nervous System Drug Discovery”. NeuroRx24 (2005): 554-571.
47. Ying Han., et al. “In Silico ADME And Toxicity Prediction Of Ceftazidime And Its Impurities”. Frontiers in Pharmacology 10 (2019): 434.
48. Pires DE., et al. “pkCSM: Predicting Small-Molecule Pharmacokinetic And Toxicity Properties Using Graph-Based Signatures”. Journal of Medicinal Chemistry 58 (2005): 4066-4072.
49. Tristani-Firouzi M., et al. “Molecular Biology Of K⁺ Channels And Their Role In Cardiac Arrhythmias”. The American Journal of Medicine1 (2001): 50-59.
50. Hsu KC., et al. “iGemdock: A Graphical Environment Of Enhancing GEMDOCK Using Pharmacological Interactions And Post-Screening Analysis”. BMC Bioinformatics 12 (2011): 1-11.

Citation

Citation: SN Saravanamoorthy., et al. “Molecular Geometry, Vibrational Spectroscopic, Molecular Orbital and Mulliken Charge Analysis of 4-(carboxyamino)-benzoic acid: Molecular Docking and DFT Calculations". Acta Scientific Pharmaceutical Sciences 5.11 (2020): 70-88.

Copyright

Copyright: © 2020 SN Saravanamoorthy., et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.