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Bir Florlu Aminoimidazolin Olan Midaflur'un Karşılaştırmalı Kuantum Kimyasal Analizi

Year 2022, Volume: 9 Issue: 1, 433 - 452, 30.06.2022
https://doi.org/10.35193/bseufbd.1075723

Abstract

Flor içeren heterosiklik bileşiklerin farmasötik kimyadaki dikkat çekici başarılarından esinlenilen bu çalışmada, iskelet-kas gevşetici ve merkezi sinir sistemi (MSS) depresan özelliklerine sahip midaflur bileşiği üzerinde kuantum kimyasal hesaplamalar yapılmıştır.Öncelikle midaflur'un her iki tautomerik yapısı için toplam enerji (ΔETotal), entalpi (ΔH) ve Gibbs serbest enerji (ΔG) değerleri hesaplanarak hangi formun daha kararlı olduğu belirlendi ve çalışmaya bu yapı üzerinden devam edildi.Kararlı amino formuna ait geometrik parametreleri incelemek için HF yöntemi ve B3LYP/B3PW91 DFT fonksiyonelleri farklı temel setlerle kullanılmıştır.Sonuçların literatürde verilen deneysel değerlerle uyum içinde olduğu belirlenmiştir.Ayrıca FT-IR analizi, Mulliken popülasyon analizi, sınır moleküler orbital (FMO) analizi, doğal bağ orbital (NBO) analizi, doğrusal olmayan optik (NLO) özellikler ve elektrostatik yüzey özellikleri detaylı olarak incelenmiştir.Çalışmanın başka bir bölümünde, bir ilacın MSS'ye giriş için lipofilitesinin sayısal ifadesi olan logPow (n-oktanol/su partisyon katsayısının logaritması) değeri midaflur için tahmin edilmiştir.Bu amaçla, bu çalışmada kullanılan tüm metodolojiler için yoğunluğa dayalı evrensel solvasyon modeli (SMD) kullanılarak su ve n-oktanol fazları için hesaplamalar tekrarlanmış ve solvasyon serbest enerji değerleri tahmin edilmiştir. Hesaplamalı yöntemlerin tahmin gücünün HF < B3PW91 < B3LYP sırasına göre arttığı sonucuna varılmıştır.

References

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Comparative Quantum Chemical Analysis of Midaflur, a Fluorinated Aminoimidazoline

Year 2022, Volume: 9 Issue: 1, 433 - 452, 30.06.2022
https://doi.org/10.35193/bseufbd.1075723

Abstract

Inspired by the striking achievements of fluorine-containing heterocyclic compounds in pharmaceutical chemistry, in this study quantum chemical calculations were carried out on the midaflur compound, which has skeletal-muscle relaxant and central nervous system (CNS) depressant properties. First of all, the total energy (ΔETotal), enthalpy (ΔH), and Gibbs free energy (ΔG) values for both tautomeric structures of midaflur were calculated and it was determined which form was more stable and the rest of the study was continued on this structure. For the stable amino form, the HF method and B3LYP/B3PW91 DFT functionals with different basis sets were used in order to examine the geometric parameters. The results were found to be in good agreement with the experimental values given in the literature. Furthermore, FT-IR analysis, Mulliken population analysis, frontier molecular orbital (FMO) analysis, natural bond orbital (NBO) analysis, nonlinear optical (NLO) properties, and electrostatic surface properties were studied in detail. In another part of the study, the logPow (logarithm of the n-octanol/water partition coefficient) value, which is the numerical expression of the lipophilicity of a drug for entry into the CNS, was estimated for midaflur. For this purpose, the calculations were repeated for the water and n-octanol phases using the universal solvation model based on density (SMD) for all the methodologies used in this study, and the free energies of solvation were predicted. It was concluded that the predictive power of the computational methods increased in the order of HF < B3PW91 < B3LYP.

References

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  • Tri, N. N., Hailu, Y. M., Duong, L. V., & Nguyen, M. T. (2020). Influence of fluorination on energetic parameters of silole, phosphole, thiophene, oligomers of silole and related acenes.Journal of Fluorine Chemistry, 240, 109665.
  • Bogdanov, A. V., Zaripova, I. F., Voloshina, A. D., Sapunova, A. S., Kulik, N. V., Tsivunina, I. V., Dobrynin, A. B., & Mironov, V. F.(2019). Isatin derivatives bearing a fluorine atom. Part 1: Synthesis, hemotoxicity and antimicrobial activity evaluation of fluoro-benzylated water-soluble pyridinium isatin-3-acylhydrazones. Journal of Fluorine Chemistry, 227,109345.
  • Hong, F., Li, H., Zhu, D., Xia, Z., Zhang, H., Wang, H., & Zeng, Z. (2014). Piperidine and 3,3,4,4,5,5-hexafluoropiperidine as terminal groups: Syntheses and properties as new liquid crystals. Journal of Fluorine Chemistry, 168, 61–68.
  • Lipunova, G. N., Nosova, E. V., Charushin, V. N., & Chupakhin, O. N. (2016). Fluorine-containing indazoles: synthesis and biological activity. Journal of Fluorine Chemistry, 192, 1–21.
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  • Feizi-Dehnayebi, M., Dehghanian, E., & Mansouri-Torshizi, H. (2021). DNA/BSA binding affinity studies of new Pd (II) complex with S-S and N-N donor mixed ligands via experimental insight and molecular simulation: Preliminary antitumor activity, lipophilicity and DFT perspective. Journal of Molecular Liquids, 344(1), 117853.
  • Serdaroğlu, G., & Elik, M. (2018). A computational study predicting the chemical reactivity behavior of 1-substituted 9-ethyl-βCCM derivatives: DFT- based quantum chemical descriptors.Turkish Computational and Theoretical Chemistry, 2(1), 1-11.
  • Sayın, K., & Üngördü, A., (2019). Investigations of structural, spectral and electronic properties of enrofloxacin and boron complexes via quantum chemical calculation and molecular docking. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 220, 117102.
  • Serdaroğlu, G., & Ortiz, J. V. (2017). Ab initio calculations on some antiepileptic drugs such as phenytoin, phenobarbital, ethosuximide and carbamazepine.Structural Chemistry, 28, 957-964.
  • Üngördü, A., & Sayın, K. (2019). Quantum chemical calculations on sparfloxacin and boron complexes. Chemical Physics Letters, 733, 136677.
  • Feizi-Dehnayebi, M., Dehghanian, E., & Mansouri-Torshizi, H. (2021). Synthesis and characterization of Pd (II) antitumor complex, DFT calculation and DNA/BSA binding insight through the combined experimental and theoretical aspects.Journal of Molecular Structure, 1240, 130535.
  • 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. V., 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., Egidi, 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, J. A. Jr., Peralta, J. E., Ogliaro, F., Bearpark, M. J., Heyd, J. J., Brothers, E. N., Kudin, K. N., Staroverov, V. N., Keith, T. A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A. P., 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, Rev.D.01, Gaussian, Inc., Wallingford CT, 2009.
  • Becke, A. D. (1993). A new mixing of Hartree–Fock and local density functional theories.Journal of Chemical Physics, 98, 1372–1377.
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Details

Primary Language English
Journal Section Articles
Authors

Sümeyya Serin 0000-0002-4637-1734

Publication Date June 30, 2022
Submission Date February 18, 2022
Acceptance Date June 20, 2022
Published in Issue Year 2022 Volume: 9 Issue: 1

Cite

APA Serin, S. (2022). Comparative Quantum Chemical Analysis of Midaflur, a Fluorinated Aminoimidazoline. Bilecik Şeyh Edebali Üniversitesi Fen Bilimleri Dergisi, 9(1), 433-452. https://doi.org/10.35193/bseufbd.1075723