Research Article
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Year 2024, , 512 - 518, 29.06.2024
https://doi.org/10.17798/bitlisfen.1469293

Abstract

References

  • [1] H. Kolancilar, “DFT Yöntemi Kullanılarak 1,3-Bis- {(2-Aminobenzoil) Amino} Propanın Teorik Hesaplamaları Ve Bu Değerlerin Literatürdeki Deneysel Değerler İle Karşılaştırılması”, Düzce Üniversitesi Bilim Ve Teknol. Derg., vol. 7, no 3, pp. 1319-1334, Tem. 2019, doi: 10.29130/dubited.463963.
  • [2] L. Liu and H. Miao, “A Specification-Based Approach to Testing Polymorphic Attributes”,in Formal Methods and Software Engineering, vol. 3308, J. Davies, W. Schulte, ve M. Barnett, Ed., ine Lecture Notes in Computer Science, vol. 3308. , Berlin, Heidelberg: Springer Berlin Heidelberg, 2004, pp. 306-319. doi: 10.1007/978-3-540-30482-1_28.
  • [3] T. Yu, Z. Zhu, Y. Bao, Y. Zhao, X. Liu, and H. Zhang, “Investigation of novel carbazole-functionalized coumarin derivatives as organic luminescent materials”, Dyes Pigments, vol. 147, pp. 260-269, Ara. 2017, doi: 10.1016/j.dyepig.2017.08.017.
  • [4] M. S. A. Abdel-Mottaleb, E. Hamed, M. Saif, and H. S. Hafez, “Binding, and thermodynamics of β-cyclodextrin inclusion complexes with some coumarin laser dyes and coumarin-based enzyme substrates: a simulation study”, J. Incl. Phenom. Macrocycl. Chem., vol. 92, no 3-4, pp. 319-327, Ara. 2018, doi: 10.1007/s10847-018-0850-9.
  • [5] “Frisch, M. J. E. A. (2009). gaussian 09, Revision d. 01, Gaussian. Inc, Wallingford CT, 201.”.
  • [6] “T. K. R. Dennington and J. Millam, GaussView, Version 5 (Semichem Inc., Shawnee Mission, KS, 2009).”.
  • [7] T. J. Gilligan ve G. Schwarz, “The self-association of adenosine-5’-triphosphate studied by circular dichroism at low ionic strengths”, Biophys. Chem., vol. 4, no 1, pp. 55-63, Oca. 1976, doi: 10.1016/0301-4622(76)80007-5.
  • [8] X. Du vd., “Synthesis and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain”, J. Med. Chem., c. 45, sy 13, ss. 2695-2707, Haz. 2002, doi: 10.1021/jm010459j.
  • [9] R. A. Omar, P. Koparir, K. Sarac, M. Koparir, and D. A. Safin, “A novel coumarin-triazole-thiophene hybrid: synthesis, characterization, ADMET prediction, molecular docking and molecular dynamics studies with a series of SARS-CoV-2 proteins”, J. Chem. Sci., vol. 135, no 1, p. 6, Oca. 2023, doi: 10.1007/s12039-022-02127-0.
  • [10] N. M. O’boyle, A. L. Tenderholt, and K. M. Langner, “cclib: A library for package-independent computational chemistry algorithms”, J. Comput. Chem., vol. 29, no 5, pp. 839-845, 2008, doi: 10.1002/jcc.20823.
  • [11] M. Franco-Pérez ve J. L. Gázquez, “Electronegativities of Pauling and Mulliken in Density Functional Theory”, J. Phys. Chem. A, vol. 123, no 46, pp. 10065-10071, Kas. 2019, doi: 10.1021/acs.jpca.9b07468.
  • [12] J. A. Harrison, J. D. Schall, S. Maskey, P. T. Mikulski, M. T. Knippenberg, ve B. H. Morrow, “Review of force fields and intermolecular potentials used in atomistic computational materials research”, Appl. Phys. Rev., vol. 5, no 3, p. 031104, Ağu. 2018, doi: 10.1063/1.5020808.
  • [13] E. V. Schmidt vd., “Antiviral Activity of Jodantipyrin – An Anti-Inflammatory Oral Therapeutic with Interferon-Inducing Properties”, Anti-Inflamm. Anti-Allergy Agents Med. Chem., vol. 7, no 2, pp. 106-115.
  • [14] C. H. Reynolds, B. A. Tounge, and S. D. Bembenek, “Ligand Binding Efficiency: Trends, Physical Basis, and Implications”, J. Med. Chem., vol. 51, no 8, pp. 2432-2438, Nis. 2008, doi: 10.1021/jm701255b.
  • [15] S. Schultes, C. de Graaf, E. E. J. Haaksma, I. J. P. de Esch, R. Leurs, ve O. Krämer, “Ligand efficiency as a guide in fragment hit selection and optimization”, Drug Discov. Today Technol., vol. 7, no 3, pp. e157-e162, Eyl. 2010, doi: 10.1016/j.ddtec.2010.11.003.
  • [16] J. Hughes, S. Rees, S. Kalindjian, and K. Philpott, “Principles of early drug discovery”, Br. J. Pharmacol., vol. 162, no 6, pp. 1239-1249, 2011, doi: 10.1111/j.1476-5381.2010.01127.x.

New Coumarin Ring-Containing Ester Molecule: Facile Synthesis, Characterization, Computational Studies and SwissADME Prediction

Year 2024, , 512 - 518, 29.06.2024
https://doi.org/10.17798/bitlisfen.1469293

Abstract

The aim of the study was to synthesize 4-Coumarinyl-2-methylbenzoate, elucidate the reaction mechanism, perform quantum chemical calculations, and examine the swiss adme properties of the compound. 4-Coumarinyl-2-methylbenzoate compound was synthesized by nucleophilic substitution reaction. The compound 4-coumarinyl 2-methyl benzoate has been characterized both experimentally and theoretically using quantum chemical calculations and spectral techniques. Nuclear magnetic resonances and infrared spectroscopic values of 1H and 13C in the ground state of the compound were calculated both experimentally and theoretically (density functional theory method was used when making theoretical calculations). It was observed that the calculated infrared and nuclear magnetic resonance values were compatible with the experimental values. The energy difference between the HOMO-LUMO of the 4-Coumarinyl-2-methylbenzoate compound was calculated and it was found that this difference was 1.409 Ev.
Finally, swiss adme properties of 4-Coumarinyl-2-methylbenzoate compound such as Molecular Mass (Size), Flexibility (FLEX), Polarity, Saturation (Insatu), Lipophilia, Water Solubility were examined.

References

  • [1] H. Kolancilar, “DFT Yöntemi Kullanılarak 1,3-Bis- {(2-Aminobenzoil) Amino} Propanın Teorik Hesaplamaları Ve Bu Değerlerin Literatürdeki Deneysel Değerler İle Karşılaştırılması”, Düzce Üniversitesi Bilim Ve Teknol. Derg., vol. 7, no 3, pp. 1319-1334, Tem. 2019, doi: 10.29130/dubited.463963.
  • [2] L. Liu and H. Miao, “A Specification-Based Approach to Testing Polymorphic Attributes”,in Formal Methods and Software Engineering, vol. 3308, J. Davies, W. Schulte, ve M. Barnett, Ed., ine Lecture Notes in Computer Science, vol. 3308. , Berlin, Heidelberg: Springer Berlin Heidelberg, 2004, pp. 306-319. doi: 10.1007/978-3-540-30482-1_28.
  • [3] T. Yu, Z. Zhu, Y. Bao, Y. Zhao, X. Liu, and H. Zhang, “Investigation of novel carbazole-functionalized coumarin derivatives as organic luminescent materials”, Dyes Pigments, vol. 147, pp. 260-269, Ara. 2017, doi: 10.1016/j.dyepig.2017.08.017.
  • [4] M. S. A. Abdel-Mottaleb, E. Hamed, M. Saif, and H. S. Hafez, “Binding, and thermodynamics of β-cyclodextrin inclusion complexes with some coumarin laser dyes and coumarin-based enzyme substrates: a simulation study”, J. Incl. Phenom. Macrocycl. Chem., vol. 92, no 3-4, pp. 319-327, Ara. 2018, doi: 10.1007/s10847-018-0850-9.
  • [5] “Frisch, M. J. E. A. (2009). gaussian 09, Revision d. 01, Gaussian. Inc, Wallingford CT, 201.”.
  • [6] “T. K. R. Dennington and J. Millam, GaussView, Version 5 (Semichem Inc., Shawnee Mission, KS, 2009).”.
  • [7] T. J. Gilligan ve G. Schwarz, “The self-association of adenosine-5’-triphosphate studied by circular dichroism at low ionic strengths”, Biophys. Chem., vol. 4, no 1, pp. 55-63, Oca. 1976, doi: 10.1016/0301-4622(76)80007-5.
  • [8] X. Du vd., “Synthesis and Structure−Activity Relationship Study of Potent Trypanocidal Thio Semicarbazone Inhibitors of the Trypanosomal Cysteine Protease Cruzain”, J. Med. Chem., c. 45, sy 13, ss. 2695-2707, Haz. 2002, doi: 10.1021/jm010459j.
  • [9] R. A. Omar, P. Koparir, K. Sarac, M. Koparir, and D. A. Safin, “A novel coumarin-triazole-thiophene hybrid: synthesis, characterization, ADMET prediction, molecular docking and molecular dynamics studies with a series of SARS-CoV-2 proteins”, J. Chem. Sci., vol. 135, no 1, p. 6, Oca. 2023, doi: 10.1007/s12039-022-02127-0.
  • [10] N. M. O’boyle, A. L. Tenderholt, and K. M. Langner, “cclib: A library for package-independent computational chemistry algorithms”, J. Comput. Chem., vol. 29, no 5, pp. 839-845, 2008, doi: 10.1002/jcc.20823.
  • [11] M. Franco-Pérez ve J. L. Gázquez, “Electronegativities of Pauling and Mulliken in Density Functional Theory”, J. Phys. Chem. A, vol. 123, no 46, pp. 10065-10071, Kas. 2019, doi: 10.1021/acs.jpca.9b07468.
  • [12] J. A. Harrison, J. D. Schall, S. Maskey, P. T. Mikulski, M. T. Knippenberg, ve B. H. Morrow, “Review of force fields and intermolecular potentials used in atomistic computational materials research”, Appl. Phys. Rev., vol. 5, no 3, p. 031104, Ağu. 2018, doi: 10.1063/1.5020808.
  • [13] E. V. Schmidt vd., “Antiviral Activity of Jodantipyrin – An Anti-Inflammatory Oral Therapeutic with Interferon-Inducing Properties”, Anti-Inflamm. Anti-Allergy Agents Med. Chem., vol. 7, no 2, pp. 106-115.
  • [14] C. H. Reynolds, B. A. Tounge, and S. D. Bembenek, “Ligand Binding Efficiency: Trends, Physical Basis, and Implications”, J. Med. Chem., vol. 51, no 8, pp. 2432-2438, Nis. 2008, doi: 10.1021/jm701255b.
  • [15] S. Schultes, C. de Graaf, E. E. J. Haaksma, I. J. P. de Esch, R. Leurs, ve O. Krämer, “Ligand efficiency as a guide in fragment hit selection and optimization”, Drug Discov. Today Technol., vol. 7, no 3, pp. e157-e162, Eyl. 2010, doi: 10.1016/j.ddtec.2010.11.003.
  • [16] J. Hughes, S. Rees, S. Kalindjian, and K. Philpott, “Principles of early drug discovery”, Br. J. Pharmacol., vol. 162, no 6, pp. 1239-1249, 2011, doi: 10.1111/j.1476-5381.2010.01127.x.
There are 16 citations in total.

Details

Primary Language English
Subjects Computational Chemistry
Journal Section Araştırma Makalesi
Authors

Kamuran Saraç 0000-0001-6684-8969

Early Pub Date June 27, 2024
Publication Date June 29, 2024
Submission Date April 16, 2024
Acceptance Date June 27, 2024
Published in Issue Year 2024

Cite

IEEE K. Saraç, “New Coumarin Ring-Containing Ester Molecule: Facile Synthesis, Characterization, Computational Studies and SwissADME Prediction”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 13, no. 2, pp. 512–518, 2024, doi: 10.17798/bitlisfen.1469293.



Bitlis Eren Üniversitesi
Fen Bilimleri Dergisi Editörlüğü

Bitlis Eren Üniversitesi Lisansüstü Eğitim Enstitüsü        
Beş Minare Mah. Ahmet Eren Bulvarı, Merkez Kampüs, 13000 BİTLİS        
E-posta: fbe@beu.edu.tr