Synthesis of Pyridine-Based Imine Compounds and Molecular Docking Studies Against Dopamine D2 Receptors

Abstract

In this study, new pyridine-based imine compounds (8-10) were synthesized and docking studies of these compounds against D2 Dopamine receptor (6CM4) were performed. The structures of these compounds, which were synthesized using the microwave method, were determined by 1H-NMR, 13C-NMR and elemental analysis techniques. The binding energy values vary range from -6.79 to -7.07 kcal/mol with D2 Dopamine Receptor/PDB: 6MC4. Compound 10 (-7.07 kcal mol-1) showed better binding energy than 9 (-6.95 kcal mol-1) and 8 (-6.79 kcal/mol).

Keywords

• β-Phenylethylamine
• Dopamine
• Imine
• D2 receptor
• Molecular docking

References

1. 1. Koçak D. β-Benzil ve β-Fenil Sübstitüeye Yeni Dopamin Analoğu Bileşikler ve Bunların Sülfamit Türevlerinin Sentezi. Atatürk Üniversitesi Fen Bilimleri Enstitüsü Yüksek Lisans Tezi (2016).
2. 2. Xiaomin C, Qin M, Li P, Zhou B, Tang X, Ge M, Yang L, Liu J. Probing catecholamine neurotransmitters based on ironcoordination surface enhanced resonance Raman spectroscopy label. Sensors and Actuators B 268 (2018) 350-358.
3. 3. Mo JW and Ogorevc B. Simultaneous measurement of dopamine and ascorbate at their physiological levels using voltammetric microprobe based on overoxidized poly (1,2-phenylenediamine)- coated carbon fiber. Anal. Chem. 73, 6 (2001) 1196-1202.
4. 4. Naderi A. α-Benzil Dopamin ve Bazı Sülfamit Türevlerinin İlk Sentezi. Atatürk Üniversitesi Fen Bilimleri Enstitüsü Doktora Tezi. 2017.
5. 5. Haadsma-Svensson SR, Svensson KA. PNU-99194A:A preferential dopamine D3 receptor antagonist. CNS Drug Rev. 4 (1998) 42-53.
6. 6. Aksu K. Dopamin Benzeri Bileşiklerin Sülfamit Türevlerinin Sentezi. Atatürk Üniversitesi Fen Bilimleri Enstitüsü Doktora Tezi. (2014).
7. 7. Cannon JG. Dopamine agonists: structure-activity relationships. Progress in Drug Research. 29 (1985) 303-414.
8. 8. Riederer P and Laux G. MAO-inhibitors in Parkinson’s Disease. Experimental Neurobiology 20 (2011) 1-17.

9. 9. Saikia A, Bhattacharya P, Paul S. Importance of dopamine in Parkinson’s disease. Advances in Tissue Engineering and Regenerative Medicine 4, 3, (2018) 47-48.
10. 10. Summakoğlu D. and Ertuğrul B. Schızophrenıa and its Treatment. Lectio Scientific Journal of Health and Natural Sciences 2,1 (2018) 43-61.
11. 11. Peiyan N, Linhui L, Yingcheng W, Jinxue W, Xiaochu G, Z, Xiaohong M, Tao L. Risperidone regulates Dopamine D2-like receptors expression in rat brain in a time-dependent manner. Eur. J. Psychiat. 29, 1 (2015) 33-43.
12. 12. Minwalla HD, Wrzesinski P, Desforges A, Caskey J, Wagner B, Ingraffia P, Patterson II JC, Edinoff AN, Kaye AM, Kaye AD, Viswanath O, and Urits I. Paliperidone to Treat Psychotic Disorders. Neurol. Int. 13 (2021) 343-358.
13. 13. Sabelli HC, Mosnaim AD, Vazquez AJ, Giardina WJ, Borison RL Pedemonte WA. Biochemical plasticity of synaptic transmission: A critical review of Dale's Principle.Biological Psychiatry 11, 4 (1976) 481–524.
14. 14. Hatim IH, Al-Masoudi WA, Ghadhban RF. Synthesis, characterization and acute toxicity of new Schiff base derived from phenylethyl amine and 2-hydroxy naphthaldehyde. European Journal of Chemistry 10, 1 (2019) 26-29.
15. 15. Percot A, Yalcın A, Aysel A, Erdugan H. β-Phenylethylamine content in marine algae around Turkish coasts. Botanica Marina 52 (2009) 87–90.
16. 16. Zawodny W and Montgomery SL. Evolving New Chemistry: Biocatalysis for the Synthesis of Amine-Containing Pharmaceuticals. Catalysts 12 (2022) 595.
17. 17. Ömerustaoğlu H, 5-Pirazolon-Üre Türevli Schiff Bazlarının Sentezi ve Karakterizasyonu. Ordu Üniversitesi Fen bilimleri Ents. Yüksek Lisans Tezi (2017).
18. 18. Nayak SG, Poojar B, Synthesis of novel Schiff bases containing arylpyrimidines as promising antibacterial agents. Heliyon 5 (2019) e02318.
19. 19. Özgen A and Ünlü N, Moleküler Kenetleme (Docking) Yöntemi ile Bakteriyel Bir Sinyal Kompleksi ve Peonidin Molekülü Etkileşiminin İncelenmesi Fırat Üniversitesi Fen Bilimleri Dergisi 34(2) (2022) 201-206.
20. 20. Bıcak B, Kecel Gunduz S, Kokcu Ozel AE, Akyuz S. Molecular Docking and Molecular Dynamics Studies of L-Glycyl-L-Glutamic Acid Dipeptide. Bilge International Journal of Science and Technology Research. 3 (1) (2019) 1-9.
21. 21. Bhargava K, Nath R, Seth PK, Pant KK and Dixit RK. Molecular Docking studies of D2 Dopamine receptor with Risperidone derivatives. Bioinformation 10(1) (2014) 008-012.
22. 22. Marić S, Hasić N, Horozić E, Cipurković A, Antić A, Zerina M, Pelemiš K, Brkić K, Bjelošević D. Synthesıs, Characterızatıon and Bıoactıvıty of Selected Metal Complexes Wıth Imıne Lıgands. Technologica Acta, 13, 2 (2020) 39-42.
23. 23. Ayaz M, Gündoğdu Ö, Aytaç S, Erdem B, Çiftçi H, and Erdogdu Y. Microwave-assisted synthesis, characterizations, antimicrobial activities, and DFT studies on some pyridine derived Schiff bases. Journal of Molecular Structure 1269, (2022) 133791.
24. 24. Aytaç S. Schiff Bazı Bileşiklerinin Çevreci Bir Yöntemle Yeniden Sentezi. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi 11(4) (2021) 2979-2991.
25. 25. Morris GM, Doodsell DS, Pique ME, Lindstrom W L, Huey R, Forli S, Hart W E, Halliday S, Belew R, Olson AJ, Automated docking of flexible lagands to flexible receptors, (2014).