Research Article
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The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives

Year 2023, Volume: 36 Issue: 4, 1795 - 1809, 01.12.2023

Yadigar Gülseven Sıdır , İsa Sıdır

https://doi.org/10.35378/gujs.1051216

Abstract

The electronic, hydrophobic and global reactivity parameters of modeled 28 different 5,8-quinolinequinone derivatives have been calculated using DFT (B3LYP)/6-31G(d,p) method and basis set. The molecular descriptors are chosen molecular polarizability, dipole moment, frontier molecular orbital energy, molecular volume, ionization potential, electron affinity, electronegativity, molecular hardness, molecular softness, electrophilic index, molar refractivity, octanol–water partition coefficient, entropy and capacity of heat. The relations between molecular descriptors have been investigated dependent on their correlations. QSAR/QSPR models have been derived for anti-proliferative and anti-inflammatory activity of these 5, 8-quinolinequinone (s) derivatives. The dependence of the electronegativity parameter on both electronic and thermochemical parameters is found to be the best correlated parameter.

Keywords

5-8-Quinolinequinones DFT QSAR QSPR Biological activity

Supporting Institution

BİTLİS EREN UNIVERSITY

Thanks

The authors greatly acknowledge to Bitlis Eren University for providing Gaussian09W and GausView5.0.

References

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  • [2] Hansch, C., Leo, A., Taft, R. W., “A survey of Hammett substituent constants and resonance and field parameters”, Chemical Reviews, 91: 165-195, (1991).
  • [3] Gao, H., Katzenellenbogen, J. A., Garg, R., “Comparative QSAR analysis of estrogen receptor ligands”, Chemical Reviews, 99: 723-744, (1999).
  • [4] Franke, R., “Theoretical Drug Design Methods”, Elsevier: Amsterdam, 156-161, (1984).
  • [5] Gupta, S. P., Singh, M., Bindal, C., “QSAR studies on hallucinogens”, Chemical Reviews, 83: 633-649, (1983).
  • [6] Valderrama, J. A., Ibacache, J. A., Arancibia, V., Rodriquez, J., Theoduloz, C., “Studies on quinones. Part 45: Novel 7-aminoisoquinoline-5,8-quinone derivatives with antitumor properties on cancer cell lines”, Bioorganic&Medicinal Chemistry, 17: 2894-2901, (2009).
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  • [8] Cheng, Y., An, L. K., Wu, N., Wang, X. D., Bu, X. Z., Huang, Z. S., Gu, L. Q., “Synthesis, cytotoxic activities and structure–activity relationships of topoisomerase I inhibitors: Indolizinoquinoline-5,12-dione derivatives”, Bioorganic&Medicinal Chemistry, 16: 4617-4625, (2008).
  • [9] Chia, E. W., Pearce, A. N., Berridge, M. V., Larsen, L., Perry, N. B., Sansom, C. E., Godfrey, C. A., Hanton, L. R., Lu, G. L., Walton, M., Denny, W., Webb, V. L., Copp, B. R., Harper, J. L., “Synthesis and anti-inflammatory structure-activity relationships of thiazine-quinoline-quinones: inhibitors of the neutrophil respiratory burst in a model of acute gouty arthritis”, Bioorganic&Medicinal Chemistry, 16: 9432-9442, (2008).
  • [10] Bolognese, A., Correale, G., Manfra, M., Esposito, A., Novellino, E., Lavecchia, A., “Antitumor Agents 6. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Spiro[imidazolidine-4,3′-thieno[2,3-g]quinoline]-tetraones and Spiro[thieno[2,3-g]quinoline-3,5′-[1,2,4]triazinane]-tetraones with Potent Antiproliferative Activity”, Journal of Medicinal Chemistry, 51: 8148-8152, (2008).
  • [11] Benjamin, J. M., Christopher, G. N., James, W. B., Carole, H. G., William, J. M., Michaela, C. W., Emma, M. D., Catherine, H. P., Michael, V. B., Jacquie, L. H., Mattie, S. M. T., Bridget, L. S. “The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones”, Bioorganic & Medicinal Chemistry, 18: 3238–3251, (2010).
  • [12] Cronin, M. T. D., “Computational methods for the prediction of drug toxicity”, Current Opinion in Drug Discovery and Development, 3: 292-297, (2000).
  • [13] Becke, A. D.,”Density functional thermochemistry III. The role of exact exchange”, Journal of Chemical Physics, 98: 5648-5652, (1993).
  • [14] Lee, C., Yang, W., Parr, R. G., “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Physical Review B, 37: 785-789, (1988).
  • [15] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A., Bloino, J., Janesko, B. G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J. V., Izmaylov, A. F., Sonnenberg, J. L., Williams-Young, D., Ding, F., Lipparini, F., Egdi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V. G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, Jr. J. A., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Millam, J. M., Klene, M., Adamo, C., Cammi, R., Ochterski, J. W., Martin, R. L., Morokuma, K., Farkas, O., Foresman, J. B., Fox, D.J., Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, USA, (2009).
  • [16] Nielsen, A. B., Holder, A., “GaussView 5.0, User’s Reference”, GAUSSIAN Inc., Pittsburgh, (2009).
  • [17] IBM Corp. Released. IBM SPSS Statistics for Windows, Version 23.0. Armonk, NY: IBM Corp, (2015).
  • [18] Lien, E. J., Guo, Z.R., “Use of Dipole moment as a Parameter in Drug-Receptor Interaction and Quantitative Structure-Activity Relationship Studies”, Journal of Pharmaceutical Sciences 71(6): 641-655, (1982).
  • [19] Kujawski, J., Popielarska, H., Myka, A., Drabińska, B., Bernard, M. K., “The log P Parameter as a Molecular Descriptor, in the Computer-aided Drug Design – an Overview”, Computational Methods in Science and Technology, 18(2): 81-88, (2012).
  • [20] Avdeef, A., “Physicochemical profiling (solubility, permeability and charge state)”, Current Topics in Medicinal Chemistry, 1: 277-351, (2001).
  • [21] Matoga, M., Laborde-Kummer, E., Langlois, M. H., Dallet, P., Bose, J. J., Jarry, C., Dubost, P., “Determination of pKa values of 2-amino-2-oxazolines by capillary electrophoresis”, Journal of Chromatography A, 984: 253-260, (2003).
  • [22] Remko, M., Liedl, K. R., Rode, B. M., “Structure, Reaction Enthalpies, Entropies, and Free Energies of Cation−Molecule Complexes. A Theoretical Study by Means of the ab Initio Complete Basis Set CBS-Q Method”, The Journal of Physical Chemistry A, 102: 771-777, (1998).
  • [23] Ruffolo, R. R., Bondinell, Jr. W., Hieble, J. P., “Alpha- and beta-adrenoceptors: from the gene to the clinic. 1. Molecular biology and adrenoceptor subclassification”, Journal of Medicinal Chemistry, 38: 3681-3761, (1995).
  • [24] Szabo, B., “Imidazoline antihypertensive drugs: a critical review on their mechanism of action”, Pharmacology & Therapeutics, 93: 1-35, (2002).
  • [25] Anastassiadou, M., Danoun, S., Crane, L., Baziard-Mouysset, G., Payard, M., Caignard, D. H., Rettori, M.C., Renard, P., “Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands”, Bioorganic & Medicinal Chemistry, 9: 585-592, (2001).
  • [26] Yoshida, F., Topliss, J. G., “Isoquinoline and Quinazoline Urea Analogues as Antagonists for the Human Adenosine A3 Receptor”, Journal of Medicinal Chemistry, 43: 5272-5275, (2000).
  • [27] Kubinyi, H., QSAR: Hansch analysis and Related Approaches, VCH, New York, 1-117, (1993).
  • [28] Dunn, W. J., “Molar refractivity as an independent variable in quantitative structure-activity studies”, European Journal of Medicinal Chemistry - Chimie thérapeutique, 12: 109-112, (1977).
  • [29] Darros‐Barbosa, R., Balaban, M. O., Teixeira, A. A., “Temperature and Concentration Dependence of Density of Model Liquid Foods”, International Journal of Food Properties, 6(2): 239-258, (2003).
  • [30] Varese, M., Guardiola, S., Garcia, J., Giralt, E., “Enthalpy- versus Entropy-Driven Molecular Recognition in the Era of Biologics”, ChemBioChem, 20: 2981 –2986, (2019).
  • [31] Verma, R. P., Kurup, A., Hansch, C., “On the role of polarizability in QSAR”, Bioorganic & Medicinal Chemistry, 13: 237–255, (2005).
  • [32] Pauling, L., “The Nature of the Chemical Bond”, 3rd ed., Cornell University Press: Ithaca, New York, 242-543, (1960).
  • [33] Parr, R. G., Yang, W., “Density Functional Theory of Atoms and Molecules”, Oxford University Press: Oxford, UK, (1989).
  • [34] Kumer, A., Sarkar, N., Paul, S., Zannat, A., “The Theoretical Prediction of Thermophysical properties, HOMO, LUMO, QSAR and Biological Indices of Cannabinoids (CBD) and Tetrahhdrocannabinol (THC) by Computational Chemistry”, Advanced Journal of Chemistry-Section A, 2(3): 190-202, (2019).
  • [35] Gülseven Sıdır, Y., Sıdır, İ., “Structure-activity relationships for novel drug precursor N-substituted-6-acylbenzothiazolon derivatives: A theoretical approach”, Journal of Molecular Structure, 1045: 131-138, (2013).
  • [36] Gülseven Sıdır, Y., Sıdır, İ., “Quantitative structure activity relationships of cytotoxicity effect on various cancer cells of some imidazo[1,2-α] pyrazine derivatives”, Bitlis Eren University Journal of Science and Technology, 3: 9–14, (2013).
  • [37] Topliss, J. G., Costello, R. J., “Chance Correlations in Structure-Activity Studies using Multiple Regression Analysis”, Journal of Medicinal Chemistry, 15(10): 1066-1068, (1972).

Year 2023, Volume: 36 Issue: 4, 1795 - 1809, 01.12.2023

Yadigar Gülseven Sıdır , İsa Sıdır

https://doi.org/10.35378/gujs.1051216

Abstract

Keywords

5-8-Quinolinequinones DFT QSAR QSPR Biological activity

References

  • [1] Gülseven Sıdır, Y., Sıdır, İ., Taşal, E., Öğretir, C., “A Theoretical Study on Electronic Structure and Structure-Activity Properties of Novel Drug Precursor 6-Acylbenzothiazolon Derivatives”, International Journal of Quantum Chemistry, 111: 3616–3629, (2011).
  • [2] Hansch, C., Leo, A., Taft, R. W., “A survey of Hammett substituent constants and resonance and field parameters”, Chemical Reviews, 91: 165-195, (1991).
  • [3] Gao, H., Katzenellenbogen, J. A., Garg, R., “Comparative QSAR analysis of estrogen receptor ligands”, Chemical Reviews, 99: 723-744, (1999).
  • [4] Franke, R., “Theoretical Drug Design Methods”, Elsevier: Amsterdam, 156-161, (1984).
  • [5] Gupta, S. P., Singh, M., Bindal, C., “QSAR studies on hallucinogens”, Chemical Reviews, 83: 633-649, (1983).
  • [6] Valderrama, J. A., Ibacache, J. A., Arancibia, V., Rodriquez, J., Theoduloz, C., “Studies on quinones. Part 45: Novel 7-aminoisoquinoline-5,8-quinone derivatives with antitumor properties on cancer cell lines”, Bioorganic&Medicinal Chemistry, 17: 2894-2901, (2009).
  • [7] Ryu, C. K., Lee, J. Y., Jeong, S. H., Nho, J. H., “Synthesis and antifungal activity of 1H-pyrrolo[3,2-g] quinoline-4,9-diones and 4,9-dioxo-4,9-dihydro-1H-benzo[f]indoles”, Bioorganic&Medicinal Chemistry Letter, 19: 146-148, (2009).
  • [8] Cheng, Y., An, L. K., Wu, N., Wang, X. D., Bu, X. Z., Huang, Z. S., Gu, L. Q., “Synthesis, cytotoxic activities and structure–activity relationships of topoisomerase I inhibitors: Indolizinoquinoline-5,12-dione derivatives”, Bioorganic&Medicinal Chemistry, 16: 4617-4625, (2008).
  • [9] Chia, E. W., Pearce, A. N., Berridge, M. V., Larsen, L., Perry, N. B., Sansom, C. E., Godfrey, C. A., Hanton, L. R., Lu, G. L., Walton, M., Denny, W., Webb, V. L., Copp, B. R., Harper, J. L., “Synthesis and anti-inflammatory structure-activity relationships of thiazine-quinoline-quinones: inhibitors of the neutrophil respiratory burst in a model of acute gouty arthritis”, Bioorganic&Medicinal Chemistry, 16: 9432-9442, (2008).
  • [10] Bolognese, A., Correale, G., Manfra, M., Esposito, A., Novellino, E., Lavecchia, A., “Antitumor Agents 6. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Spiro[imidazolidine-4,3′-thieno[2,3-g]quinoline]-tetraones and Spiro[thieno[2,3-g]quinoline-3,5′-[1,2,4]triazinane]-tetraones with Potent Antiproliferative Activity”, Journal of Medicinal Chemistry, 51: 8148-8152, (2008).
  • [11] Benjamin, J. M., Christopher, G. N., James, W. B., Carole, H. G., William, J. M., Michaela, C. W., Emma, M. D., Catherine, H. P., Michael, V. B., Jacquie, L. H., Mattie, S. M. T., Bridget, L. S. “The anti-cancer, anti-inflammatory and tuberculostatic activities of a series of 6,7-substituted-5,8-quinolinequinones”, Bioorganic & Medicinal Chemistry, 18: 3238–3251, (2010).
  • [12] Cronin, M. T. D., “Computational methods for the prediction of drug toxicity”, Current Opinion in Drug Discovery and Development, 3: 292-297, (2000).
  • [13] Becke, A. D.,”Density functional thermochemistry III. The role of exact exchange”, Journal of Chemical Physics, 98: 5648-5652, (1993).
  • [14] Lee, C., Yang, W., Parr, R. G., “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density”, Physical Review B, 37: 785-789, (1988).
  • [15] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A., Bloino, J., Janesko, B. G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J. V., Izmaylov, A. F., Sonnenberg, J. L., Williams-Young, D., Ding, F., Lipparini, F., Egdi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V. G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, Jr. J. A., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Millam, J. M., Klene, M., Adamo, C., Cammi, R., Ochterski, J. W., Martin, R. L., Morokuma, K., Farkas, O., Foresman, J. B., Fox, D.J., Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, USA, (2009).
  • [16] Nielsen, A. B., Holder, A., “GaussView 5.0, User’s Reference”, GAUSSIAN Inc., Pittsburgh, (2009).
  • [17] IBM Corp. Released. IBM SPSS Statistics for Windows, Version 23.0. Armonk, NY: IBM Corp, (2015).
  • [18] Lien, E. J., Guo, Z.R., “Use of Dipole moment as a Parameter in Drug-Receptor Interaction and Quantitative Structure-Activity Relationship Studies”, Journal of Pharmaceutical Sciences 71(6): 641-655, (1982).
  • [19] Kujawski, J., Popielarska, H., Myka, A., Drabińska, B., Bernard, M. K., “The log P Parameter as a Molecular Descriptor, in the Computer-aided Drug Design – an Overview”, Computational Methods in Science and Technology, 18(2): 81-88, (2012).
  • [20] Avdeef, A., “Physicochemical profiling (solubility, permeability and charge state)”, Current Topics in Medicinal Chemistry, 1: 277-351, (2001).
  • [21] Matoga, M., Laborde-Kummer, E., Langlois, M. H., Dallet, P., Bose, J. J., Jarry, C., Dubost, P., “Determination of pKa values of 2-amino-2-oxazolines by capillary electrophoresis”, Journal of Chromatography A, 984: 253-260, (2003).
  • [22] Remko, M., Liedl, K. R., Rode, B. M., “Structure, Reaction Enthalpies, Entropies, and Free Energies of Cation−Molecule Complexes. A Theoretical Study by Means of the ab Initio Complete Basis Set CBS-Q Method”, The Journal of Physical Chemistry A, 102: 771-777, (1998).
  • [23] Ruffolo, R. R., Bondinell, Jr. W., Hieble, J. P., “Alpha- and beta-adrenoceptors: from the gene to the clinic. 1. Molecular biology and adrenoceptor subclassification”, Journal of Medicinal Chemistry, 38: 3681-3761, (1995).
  • [24] Szabo, B., “Imidazoline antihypertensive drugs: a critical review on their mechanism of action”, Pharmacology & Therapeutics, 93: 1-35, (2002).
  • [25] Anastassiadou, M., Danoun, S., Crane, L., Baziard-Mouysset, G., Payard, M., Caignard, D. H., Rettori, M.C., Renard, P., “Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands”, Bioorganic & Medicinal Chemistry, 9: 585-592, (2001).
  • [26] Yoshida, F., Topliss, J. G., “Isoquinoline and Quinazoline Urea Analogues as Antagonists for the Human Adenosine A3 Receptor”, Journal of Medicinal Chemistry, 43: 5272-5275, (2000).
  • [27] Kubinyi, H., QSAR: Hansch analysis and Related Approaches, VCH, New York, 1-117, (1993).
  • [28] Dunn, W. J., “Molar refractivity as an independent variable in quantitative structure-activity studies”, European Journal of Medicinal Chemistry - Chimie thérapeutique, 12: 109-112, (1977).
  • [29] Darros‐Barbosa, R., Balaban, M. O., Teixeira, A. A., “Temperature and Concentration Dependence of Density of Model Liquid Foods”, International Journal of Food Properties, 6(2): 239-258, (2003).
  • [30] Varese, M., Guardiola, S., Garcia, J., Giralt, E., “Enthalpy- versus Entropy-Driven Molecular Recognition in the Era of Biologics”, ChemBioChem, 20: 2981 –2986, (2019).
  • [31] Verma, R. P., Kurup, A., Hansch, C., “On the role of polarizability in QSAR”, Bioorganic & Medicinal Chemistry, 13: 237–255, (2005).
  • [32] Pauling, L., “The Nature of the Chemical Bond”, 3rd ed., Cornell University Press: Ithaca, New York, 242-543, (1960).
  • [33] Parr, R. G., Yang, W., “Density Functional Theory of Atoms and Molecules”, Oxford University Press: Oxford, UK, (1989).
  • [34] Kumer, A., Sarkar, N., Paul, S., Zannat, A., “The Theoretical Prediction of Thermophysical properties, HOMO, LUMO, QSAR and Biological Indices of Cannabinoids (CBD) and Tetrahhdrocannabinol (THC) by Computational Chemistry”, Advanced Journal of Chemistry-Section A, 2(3): 190-202, (2019).
  • [35] Gülseven Sıdır, Y., Sıdır, İ., “Structure-activity relationships for novel drug precursor N-substituted-6-acylbenzothiazolon derivatives: A theoretical approach”, Journal of Molecular Structure, 1045: 131-138, (2013).
  • [36] Gülseven Sıdır, Y., Sıdır, İ., “Quantitative structure activity relationships of cytotoxicity effect on various cancer cells of some imidazo[1,2-α] pyrazine derivatives”, Bitlis Eren University Journal of Science and Technology, 3: 9–14, (2013).
  • [37] Topliss, J. G., Costello, R. J., “Chance Correlations in Structure-Activity Studies using Multiple Regression Analysis”, Journal of Medicinal Chemistry, 15(10): 1066-1068, (1972).
There are 37 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Physics
Authors

Yadigar Gülseven Sıdır 0000-0002-5329-2815

İsa Sıdır 0000-0001-6050-3775

Publication Date December 1, 2023
Published in Issue Year 2023 Volume: 36 Issue: 4

Cite

APA Gülseven Sıdır, Y., & Sıdır, İ. (2023). The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives. Gazi University Journal of Science, 36(4), 1795-1809. https://doi.org/10.35378/gujs.1051216
AMA Gülseven Sıdır Y, Sıdır İ. The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives. Gazi University Journal of Science. December 2023;36(4):1795-1809. doi:10.35378/gujs.1051216
Chicago Gülseven Sıdır, Yadigar, and İsa Sıdır. “The Study on QSAR and Relations Between Molecular Descriptors of 5, 8-Quinoline Quinones Derivatives”. Gazi University Journal of Science 36, no. 4 (December 2023): 1795-1809. https://doi.org/10.35378/gujs.1051216.
EndNote Gülseven Sıdır Y, Sıdır İ (December 1, 2023) The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives. Gazi University Journal of Science 36 4 1795–1809.
IEEE Y. Gülseven Sıdır and İ. Sıdır, “The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives”, Gazi University Journal of Science, vol. 36, no. 4, pp. 1795–1809, 2023, doi: 10.35378/gujs.1051216.
ISNAD Gülseven Sıdır, Yadigar - Sıdır, İsa. “The Study on QSAR and Relations Between Molecular Descriptors of 5, 8-Quinoline Quinones Derivatives”. Gazi University Journal of Science 36/4 (December 2023), 1795-1809. https://doi.org/10.35378/gujs.1051216.
JAMA Gülseven Sıdır Y, Sıdır İ. The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives. Gazi University Journal of Science. 2023;36:1795–1809.
MLA Gülseven Sıdır, Yadigar and İsa Sıdır. “The Study on QSAR and Relations Between Molecular Descriptors of 5, 8-Quinoline Quinones Derivatives”. Gazi University Journal of Science, vol. 36, no. 4, 2023, pp. 1795-09, doi:10.35378/gujs.1051216.
Vancouver Gülseven Sıdır Y, Sıdır İ. The study on QSAR and relations between molecular descriptors of 5, 8-quinoline quinones derivatives. Gazi University Journal of Science. 2023;36(4):1795-809.