In this study, A series of triazolo quinazolinone bearing carbohydrate moieties were synthesized to investigate their possible antibacterial and antifungal activities. Some nucleosides 3a-f were prepared by treating an aqueous ethanolic solution of hydrazino quinazolinone derivative 2 with aldohexoses and aldo-pentoses in the presence of a catalytic amount of acetic acid. Acetylation of the sugar hydrazones with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 4a-f. Attempted oxidative cyclization of the sugar hydrazones 3b,d,f following intramolecular nucleophilic substitution protocol, using one pot conditions with bromine in acetic acid in the presence of anhydrous sodium acetate, followed by acetylation with acetic anhydride afford the corresponding triazolo acetate derivatives 5b, d, f . Continuously, the reaction of the sugar hydrazones 3b, d, f with bromine water gave the corresponding quinazolino triazole derivatives 6b, d, f. On the other hand, deacetylation of triazolo per-O-acetylated derivatives 5b, d, f with methanolic ammonia gave the triazolo derivatives 6b, d, f. The structural elucidation of the products was confirmed by their elemental analyses and spectral data. To identify the experimentally observed results, quantum chemical calculations have been performed on the sugar hydrazone 3b in both forms and its precursors using a Gaussian 09 program, applying density functional method, DFT/B3LYP exchange-correlation with the 6-311G (d, p) basis set. From the output file we can consider different reactivity descriptors from frontier molecular orbitals energies such as ionization potential (IP), chemical potential (μ ), electron affinity (EA), hardness (η), softness( σ), electrophilicity and nucleophilicity, from this data we can conclude the active sites of the studied molecules and charge transfer was evidenced from quinazolin hydrazone 2 to glucose , this was in good agreement with Mulliken atomic charges calculated at DFT/B3LYP/6311. Also, optimization of the two forms of 3b takes place using Ab initio Hartree-Fock at 6-311G (d, p) basis set and semi-empirical calculations PM3&PM6 were used for calculating the optimization energies and dipole moments to compare the nature of the molecule after optimization at different levels. On the other hand, some of the synthesized compounds were screened for their antimicrobial activities using the inhibition zone diameter test, some of these compounds showed promising antibacterial and antifungal activities. "/> In this study, A series of triazolo quinazolinone bearing carbohydrate moieties were synthesized to investigate their possible antibacterial and antifungal activities. Some nucleosides 3a-f were prepared by treating an aqueous ethanolic solution of hydrazino quinazolinone derivative 2 with aldohexoses and aldo-pentoses in the presence of a catalytic amount of acetic acid. Acetylation of the sugar hydrazones with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 4a-f. Attempted oxidative cyclization of the sugar hydrazones 3b,d,f following intramolecular nucleophilic substitution protocol, using one pot conditions with bromine in acetic acid in the presence of anhydrous sodium acetate, followed by acetylation with acetic anhydride afford the corresponding triazolo acetate derivatives 5b, d, f . Continuously, the reaction of the sugar hydrazones 3b, d, f with bromine water gave the corresponding quinazolino triazole derivatives 6b, d, f. On the other hand, deacetylation of triazolo per-O-acetylated derivatives 5b, d, f with methanolic ammonia gave the triazolo derivatives 6b, d, f. The structural elucidation of the products was confirmed by their elemental analyses and spectral data. To identify the experimentally observed results, quantum chemical calculations have been performed on the sugar hydrazone 3b in both forms and its precursors using a Gaussian 09 program, applying density functional method, DFT/B3LYP exchange-correlation with the 6-311G (d, p) basis set. From the output file we can consider different reactivity descriptors from frontier molecular orbitals energies such as ionization potential (IP), chemical potential (μ ), electron affinity (EA), hardness (η), softness( σ), electrophilicity and nucleophilicity, from this data we can conclude the active sites of the studied molecules and charge transfer was evidenced from quinazolin hydrazone 2 to glucose , this was in good agreement with Mulliken atomic charges calculated at DFT/B3LYP/6311. Also, optimization of the two forms of 3b takes place using Ab initio Hartree-Fock at 6-311G (d, p) basis set and semi-empirical calculations PM3&PM6 were used for calculating the optimization energies and dipole moments to compare the nature of the molecule after optimization at different levels. On the other hand, some of the synthesized compounds were screened for their antimicrobial activities using the inhibition zone diameter test, some of these compounds showed promising antibacterial and antifungal activities. "/> In this study, A series of triazolo quinazolinone bearing carbohydrate moieties were synthesized to investigate their possible antibacterial and antifungal activities. Some nucleosides 3a-f were prepared by treating an aqueous ethanolic solution of hydrazino quinazolinone derivative 2 with aldohexoses and aldo-pentoses in the presence of a catalytic amount of acetic acid. Acetylation of the sugar hydrazones with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 4a-f. Attempted oxidative cyclization of the sugar hydrazones 3b,d,f following intramolecular nucleophilic substitution protocol, using one pot conditions with bromine in acetic acid in the presence of anhydrous sodium acetate, followed by acetylation with acetic anhydride afford the corresponding triazolo acetate derivatives 5b, d, f . Continuously, the reaction of the sugar hydrazones 3b, d, f with bromine water gave the corresponding quinazolino triazole derivatives 6b, d, f. On the other hand, deacetylation of triazolo per-O-acetylated derivatives 5b, d, f with methanolic ammonia gave the triazolo derivatives 6b, d, f. The structural elucidation of the products was confirmed by their elemental analyses and spectral data. To identify the experimentally observed results, quantum chemical calculations have been performed on the sugar hydrazone 3b in both forms and its precursors using a Gaussian 09 program, applying density functional method, DFT/B3LYP exchange-correlation with the 6-311G (d, p) basis set. From the output file we can consider different reactivity descriptors from frontier molecular orbitals energies such as ionization potential (IP), chemical potential (μ ), electron affinity (EA), hardness (η), softness( σ), electrophilicity and nucleophilicity, from this data we can conclude the active sites of the studied molecules and charge transfer was evidenced from quinazolin hydrazone 2 to glucose , this was in good agreement with Mulliken atomic charges calculated at DFT/B3LYP/6311. Also, optimization of the two forms of 3b takes place using Ab initio Hartree-Fock at 6-311G (d, p) basis set and semi-empirical calculations PM3&PM6 were used for calculating the optimization energies and dipole moments to compare the nature of the molecule after optimization at different levels. On the other hand, some of the synthesized compounds were screened for their antimicrobial activities using the inhibition zone diameter test, some of these compounds showed promising antibacterial and antifungal activities. "/> In this study, A series of triazolo quinazolinone bearing carbohydrate moieties were synthesized to investigate their possible antibacterial and antifungal activities. Some nucleosides 3a-f were prepared by treating an aqueous ethanolic solution of hydrazino quinazolinone derivative 2 with aldohexoses and aldo-pentoses in the presence of a catalytic amount of acetic acid. Acetylation of the sugar hydrazones with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 4a-f. Attempted oxidative cyclization of the sugar hydrazones 3b,d,f following intramolecular nucleophilic substitution protocol, using one pot conditions with bromine in acetic acid in the presence of anhydrous sodium acetate, followed by acetylation with acetic anhydride afford the corresponding triazolo acetate derivatives 5b, d, f . Continuously, the reaction of the sugar hydrazones 3b, d, f with bromine water gave the corresponding quinazolino triazole derivatives 6b, d, f. On the other hand, deacetylation of triazolo per-O-acetylated derivatives 5b, d, f with methanolic ammonia gave the triazolo derivatives 6b, d, f. The structural elucidation of the products was confirmed by their elemental analyses and spectral data. To identify the experimentally observed results, quantum chemical calculations have been performed on the sugar hydrazone 3b in both forms and its precursors using a Gaussian 09 program, applying density functional method, DFT/B3LYP exchange-correlation with the 6-311G (d, p) basis set. From the output file we can consider different reactivity descriptors from frontier molecular orbitals energies such as ionization potential (IP), chemical potential (μ ), electron affinity (EA), hardness (η), softness( σ), electrophilicity and nucleophilicity, from this data we can conclude the active sites of the studied molecules and charge transfer was evidenced from quinazolin hydrazone 2 to glucose , this was in good agreement with Mulliken atomic charges calculated at DFT/B3LYP/6311. Also, optimization of the two forms of 3b takes place using Ab initio Hartree-Fock at 6-311G (d, p) basis set and semi-empirical calculations PM3&PM6 were used for calculating the optimization energies and dipole moments to compare the nature of the molecule after optimization at different levels. On the other hand, some of the synthesized compounds were screened for their antimicrobial activities using the inhibition zone diameter test, some of these compounds showed promising antibacterial and antifungal activities. "/>

Call for Paper - Upcoming Issues

Efficient Synthesis, Spectral Characterization, Computational Studies and Antimicrobial Activities of Some Quinazolinone C-nucleosides Derivatives

International Journal of Applied Chemistry
© 2019 by SSRG - IJAC Journal
Volume 6 Issue 3
Year of Publication : 2019
Authors : Nagwa M. M. Hamada
10.14445/23939133/IJAC-V6I3P108
pdf
How to Cite?

Nagwa M. M. Hamada, "Efficient Synthesis, Spectral Characterization, Computational Studies and Antimicrobial Activities of Some Quinazolinone C-nucleosides Derivatives," SSRG International Journal of Applied Chemistry, vol. 6,  no. 3, pp. 40-57, 2019. Crossref, https://doi.org/10.14445/23939133/IJAC-V6I3P108

Abstract:

In this study, A series of triazolo quinazolinone bearing carbohydrate moieties were synthesized to investigate their possible antibacterial and antifungal activities. Some nucleosides 3a-f were prepared by treating an aqueous ethanolic solution of hydrazino quinazolinone derivative 2 with aldohexoses and aldo-pentoses in the presence of a catalytic amount of acetic acid. Acetylation of the sugar hydrazones with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 4a-f. Attempted oxidative cyclization of the sugar hydrazones 3b,d,f following intramolecular nucleophilic substitution protocol, using one pot conditions with bromine in acetic acid in the presence of anhydrous sodium acetate, followed by acetylation with acetic anhydride afford the corresponding triazolo acetate derivatives 5b, d, f . Continuously, the reaction of the sugar hydrazones 3b, d, f with bromine water gave the corresponding quinazolino triazole derivatives 6b, d, f. On the other hand, deacetylation of triazolo per-O-acetylated derivatives 5b, d, f with methanolic ammonia gave the triazolo derivatives 6b, d, f. The structural elucidation of the products was confirmed by their elemental analyses and spectral data. To identify the experimentally observed results, quantum chemical calculations have been performed on the sugar hydrazone 3b in both forms and its precursors using a Gaussian 09 program, applying density functional method, DFT/B3LYP exchange-correlation with the 6-311G (d, p) basis set. From the output file we can consider different reactivity descriptors from frontier molecular orbitals energies such as ionization potential (IP), chemical potential (μ ), electron affinity (EA), hardness (η), softness( σ), electrophilicity and nucleophilicity, from this data we can conclude the active sites of the studied molecules and charge transfer was evidenced from quinazolin hydrazone 2 to glucose , this was in good agreement with Mulliken atomic charges calculated at DFT/B3LYP/6311. Also, optimization of the two forms of 3b takes place using Ab initio Hartree-Fock at 6-311G (d, p) basis set and semi-empirical calculations PM3&PM6 were used for calculating the optimization energies and dipole moments to compare the nature of the molecule after optimization at different levels. On the other hand, some of the synthesized compounds were screened for their antimicrobial activities using the inhibition zone diameter test, some of these compounds showed promising antibacterial and antifungal activities.

Keywords:

quinazolinone, aldohexoses, aldopentoses, sugar hydrazones, triazolo-quinazolinone, antibacterial, antifungal, DFT, HOMO, LUMO, MEP.

References:

[1] Bartroli, J., Turmo, E., Algueró, M., Boncompte, E., Vericat, M.L., Conte, L., Ramis, J., Merlos, M., García-Rafanell, J. ; Forn, J. Synthesis and antifungal activity of 3-substituted-4 (3 H)-quinazolinones. Journal of medicinal chemistry, 1998. 41(11), 1869-1882.
[2] El-Sharief, A.M., Ammar, Y.A., Zahran, M.A., Ali, A.H. and El-Gaby, M.S.A. Amino acids in the synthesis of heterocyclic systems: The synthesis of triazinoquinazolinones, triazepinoquinazolinones and triazocinoquinazolinones of potential biological interest. Molecules, 2001, 6(3), 267-278.
[3] Panneer, Selvam, T. ; Kumar, P.V. Quinazoline marketed drugs—A review. Res. Pharm, 2011, 1(1), 1-21.
[4] Connolly, D.J., Cusack, D., O'Sullivan, T.P. and Guiry, P.J. Synthesis of quinazolinones and quinazolines. Tetrahedron, 2005, 61(43), 10153-10202.
[5] Nayyar, P.; Arpana, R. ; Mohd, I. An updated review: newer quinazoline derivatives under clinical trial. International journal of pharmaceutical and biological archives, 2011, 2(6), 1651-1657.
[6] Mhaske, S.B. ; Argade, N.P. The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron, 2006, 62(42), 9787-9826.
[7] Witt, A. ; Bergman, J. Recent developments in the field of quinazoline chemistry. Current Organic Chemistry,2003, 7(7), 659-677.
[8] Poonian, M.S. ; Nowoswiat, E.F. A total synthesis of C-nucleoside analog of virazole. The Journal of organic chemistry, 1977, 42(6), 1109-1110.
[9] Hacksell, U. ; Daves Jr, G.D. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. In Progress in medicinal chemistry, 1985, 22, 1-65.
[10] Vaněk, T., Farkaš, J. ; Gut, J. Synthesis of 3, 5-disubstituted 1, 2, 4-triazole derivatives-An alternative preparation of the C-analogue of ribavirin. Collection of Czechoslovak Chemical Communications, 1979, 44(4), 1334-1338.
[11] Awad, L. F. ; El Ashry, E. S. Synthesis and conformational analysis of seco C-nucleosides and their diseco double-headed analogues of the 1, 2, 4-triazole, 1, 2, 4-triazolo [3, 4-b] 1, 3, 4-thiadiazole. Carbohydrate research, 1998, 312(1-2), 9-22.
[12] Wagner, G.; Valz, G.; Dietzsch, B.; Fischer, G., Glucosides and xylosides of 1-phenyl-5-mercaptotetrazole and 3-methyl-4-phenyl-5-mercapto-1, 2, 4-triazole. 49. Glycosides of heterocyclic compounds. Die Pharmazie, 1974, 29(2), 90-95.
[13] El Ashry, E. S.; Awad, L.F. ; Winkler, M. A new approach to the synthesis of nucleosides of 1, 2, 4-triazole. Journal of the Chemical Society, Perkin Transactions, 2000, 1, (5), 829-834.
[14] Balbaa, M., Mansour; H., El-Sawy, H. ; El-Ashry, E.S.H. Inhibition of some hepatic glycosidases by the diseco nucleoside, 4-amino-3-(D-glucopentitol-1-yl)-5-mercapto-1, 2, 4-triazole and its 3-methyl analog. Nucleosides, Nucleotides and Nucleic Acids, 2002, 21(10), pp.695-708.
[15] Abdelaziz, Ouahrouch; Moha, Taourirte; Joachim, W. Engels; Soumaya, Benjelloun ; Hassan, B. Lazrek. Synthesis of New 1,2,3-Triazol-4-yl-quinazoline Nucleoside and Acyclonucleoside Analogues. Molecules 2014, 19, 3638-3653; doi:10.3390/molecules19033638.
[16] Kristen, H.;Meerwald, I.; Borner, A. Acyclische C-Nucleoside mit 1, 2, 4-Triazolen als Aglycon. Pharmazie, 1986, 41(8), 551-553. Kristen, H.; Meerwald, I.; BOERNER, A. Acyclic C‐Nucleosides with 1, 2, 4‐Triazoles as Aglycon. ChemInform, 1987, 18(2), no-no.
[17] Shaban, M. A. ; Nasr, A. Z. The chemistry of C-nucleosides and their analogs I: C-nucleosides of hetero monocyclic bases. Advances in heterocyclic chemistry, 1997, 68, 225.
[18] Györgydeák, Z.; Holzer, W.; Thiem, J. Cyclization reactions of N1-(glycopyranosylamino) guanidines. Carbohydrate research. 1997, 302, (3-4), 229-35.
[19] El Ashry, E. S. ; El Kilany, Y. Acyclonucleosides: part 2. diseco-Nucleosides. In Advances in heterocyclic chemistry, 1997, 68, 1-88.
[20] Abdel‐Aal, M.T.; El‐Sayed, W.A.; El‐Kosy, S.M.; El Sayed, H. El Ashry. Synthesis and Antiviral Evaluation of Novel 5‐(N‐Aryl‐aminomethyl‐1, 3, 4‐oxadiazol‐2‐yl) hydrazines and Their Sugars, 1, 2, 4‐Triazoles, Tetrazoles and Pyrazolyl Derivatives. Archiv der Pharmazie: An International Journal Pharmaceutical and Medicinal Chemistry. 2008, 341(5),307-13.
[21] AL‐Masoudi, N. A.; Issa, F. B.; AL‐Timari, U. A. Synthesis of Some Isomeric Glycosyl Derivatives of 3‐Mercapto‐1, 2, 4‐triazole Nucleosides. Bull. Soc. Chim. Belg., 1997, 106, 215.
[22] Ahmad, S. Sh. Tandem in situ generation and 1,5-electrocyclization of N-hetaryl nitrilimines. A facile methodology for synthesis of annulated 1,2,4-triazoles and their acyclo C-nucleosides, Arkivoc, 2010, (i), 33-97.
[23] El-Atawy, M. A ; Abd Al-Moaty, M. N; Amer, Adel. A Global Perspective on a Review of a Three-Year C-Nucleosides Development:2009-2011,American Journal of Chemistry. 2013, 3(4), 77-95. DOI: 10.5923/j.chemistry.20130304.01
[24] Kurasawa, Y.; Suzuki, K.; Nakamura, S.; Moriyama, K., ; Takada, A. Synthesis and Reactions of 3-(1, 2, 4-Triazol-5-yl) methylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines. Chemical and pharmaceutical bulletin, 1984, 32(12), 4752-4757.
[25] Dutta, M. M.; Goswami, B. N; Kataky, J. C. S. Studies on biologically active heterocycles. Part I. Synthesis and antifungal activity of some new aroyl hydrazones and 2, 5‐disubstituted‐1, 3, 4‐oxadiazoles. Journal of heterocyclic chemistry, 1986, 23(3), 793-795.
[26] Goswami, B. N.; Kataky, J. C. S.; Baruah, J. N. Synthesis and biological activity of bridgehead nitrogen heterocycles. Journal of heterocyclic chemistry, 1986, 23(5), 1439-1442.
[27] Wei, T. B.; Tang, J.; Liu, H.; Zhang, Y. M. Synthesis and bioactivity of some new [3-[4-methylphenoxymethyl]-4-phenyl-[1, 2, 4] triazole-5-thio] acetanilide derivatives. Indian Journal of Chemistry, 2007, 46B, 880-883.
[28] Mammino, L. Computational Chemistry Capacity Building in an Underprivileged Context: Challenges, Outcomes and Perspectives. Tanzania Journal of Science, 2012, 38(3), 95-107.
[29] Kurt, M.; Yurdakul, Ş. Molecular structure and vibrational spectra of 1, 2-bis (4-pyridyl) ethane by density functional theory and ab initio Hartree-Fock calculations. Journal of molecular structure, 2003, 654(1-3), 1-9.
[30] Asiri, Yazeed, "Ab Initio and Semi-Empirical Calculations of Cyanoligated Rhodium Dimer Complexes" (2017). Electronic Theses and Dissertations. Paper 3177. htps://dc.etsu.edu/etd/3177 .
[31] Ricca, A.; Bauschlicher Jr.; C. W. Successive H2O binding energies for Fe (H2O) N+. J. Phys. Chem. 1995, 99, 9003-9007.
[32] Rozanska, X.; van Santen, R. A.; Demuth, T.; Hutschka, F.; Hafner, J. (2003). A periodic DFT study of isobutene chemisorption in proton-exchanged zeolites: dependence of reactivity on the zeolite framework structure. The Journal of Physical Chemistry B, 2003,107(6), 1309-1315.
[33] Temelso, B.; Phan, T. N.; Shields, G. C. Computational study of the hydration of sulfuric acid dimers: Implications for acid dissociation and aerosol formation. The Journal of Physical Chemistry A, 2012, 116(39), 9745-9758.
[34] Hamada, Nagwa, M.M. Synthesis, Spectroscopic Characterization, and Time‐Dependent DFT Calculations of 1‐Methyl‐5‐phenyl‐5H‐pyrido[1,2‐a]quinazoline‐3,6‐dione and Its Starting Precursor in Different Solvents. Chemistry Open, 2018, 7(10), 814-823. https://doi.org/10.1002/open.201800146.
[35] Hamada, Nagwa, M. M.; Alshimaa Abd Elgawad. Experimental and Computational Study of Antioxidant Activities of Synthetic Heterocyclic Quinazoline-4-one Derivatives. American Journal of Organic Chemistry 2019, 9(1): 14-24 DOI: 10.5923/j.ajoc.20190901.03
[36] Frisch, M. J.; Hratchian, H. P.; Nielsen, A. B. Gaussian 09: Programmer's Reference. gaussian, 2009. [37] Shaban, M. A.; Nasr, A. Z. The chemistry of C-nucleosides and their analogs I: C-nucleosides of hetero monocyclic bases. Advances in heterocyclic chemistry, 1997, 68, 225. [38] Shaban, Μ. A., Taha, Μ. A.; Hamouda, Η. M. Synthesis and antimicrobial activities of condensed and uncondensed 1, 2, 4-triazines. Heterocyclic Communications, 1998, 4(4), 351-360. [39] Liu, W., Wise, D. S., & Townsend, L. B. Dimetalation of Pyrazines. A One-Pot Synthesis of Multi substituted Pyrazine C-Nucleosides. The Journal of organic chemistry, 2001, 66(14), 4783-4786. [40] Saleh, M. A.; Abdel‐Megeed, M. F.; Abdo, M. A.; Shkor, A. B. M. Synthesis of Aldehydo Sugar (4‐oxoquinazolin‐2‐yl) hydrazones and their transformation into 1‐(alditol‐1‐yl)‐1, 2, 4‐triazolo‐[4, 3‐a] quinazolin‐5 (4H)‐ones. Journal of heterocyclic chemistry, 2003, 40(1), 85-92.
[41] Sallam, M. A. CD and NMR assignment of the anomeric configuration of 4-(5-deoxy-α, β-l-arabinofuranosyl)-2-phenyl-2H-1, 2, 3-triazole C-nucleoside analogs. Carbohydrate research, 2010, 345(3), 341-345. [42] Khattab, S. N.; Hassan, S. Y.; Bekhit, A. A.; El Massry, A. M.; Langer, V.; Amer, A. Synthesis of new series of quinoxaline-based MAO-inhibitors and docking studies. European journal of medicinal chemistry, 2010, 45(10), 4479-4489.
[43] Shawali, A.S.; Sami, M.; Sherif, S.M.; Párkányi, C., Synthesis of some derivatives of imidazo [1, 2‐a] pyridine, pyrazolo [1,5‐b] imidazole, and 4‐(3H) quinazolinone from α‐ketohydrazidoyl bromides. Journal of Heterocyclic Chemistry, 1980, 17(5), 877-880.
[44] Al-Ahmary ,K. M.; Mekheimer,R. A. ; Al-Enezi ,M. S.; Hamada, Nagwa, M.M. and Habeeb, Moustafa, M. Synthesis, spectrophotometric characterization and DFT computational study of a novel quinoline derivative,2-amino-4-(2,4,6-trinitrophenylamino)-quinoline-3-carbonitrile. Journal of Molecular Liquids, 2018, 249, 501–510. [45] Hamada, Nagwa M. M.; El Sekily Mohamed A. and Mancy, Sohila H. Computational Determination of Reactivity Descriptors, Vibrational Analysis and Nuclear Magnetic Resonance of (E)-5-oxo-1-phenyl-4-(2-phenylhydrazono)-4,5-dihydro- 1H-pyrazole-3-carbaldehyde. American Scientific Research Journal for Engineering, Technology, and Sciences (ASRJETS), 2019, 61(1), 75-91. [46] Domingo,L.R.; Chamorro, E. ; Pérez, P. "Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study". Journal of Organic Chemistry, 2008, 73, 4615–4624.
[47] Jaramillo, P. et al. "A further exploration of a nucleophilicity index based on the gas-phase ionization potentials". J. Mol. Struct.: THEOCHEM, 2008, 865(1-3), 68-72.
[48] Deuri, S.; Phukan, P. "A DFT study on nucleophilicity and site selectivity of nitrogen nucleophiles". Computational and Theoretical Chemistry, 2012, 980, 49-55.
[49] Garza, A.J. ; Scuseria, G.E. ; Khan, S.B.; Asiri, A.M. Assessment of long-range corrected functionals for the prediction of non-linear optical properties of organic materials. Phys. Lett., 2013, 575, 122–125.
[50] Ansari, F.L.; Nazir, S.; Noureen, H.; Miraza, B. Combinatorial synthesis and antibacterial evaluation of an indexed chalcone library. Chem. Biodivers. 2005, 2, 1656–1664.
[51] Prabavathi, N.; Nayaki, S.N. "The spectroscopic (FT-IR, FT-Raman and NMR), first order hyperpolarizability and HOMO–LUMO analysis of 2-mercapto-4(3H)-quinazolinone". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 129, 572–583, 2014.