Microvawe assisted synthesis of N-(methyl and methoxy) benzylidene-4-fluoroaniline derivatives and their carbonic anhydrase I and II inhibition properties
Their inhibitory effects were studied on carbonic anhydrase isozymes (hCA I and II), purified from human erythrocyte cells by Sepharose-4B-L-tyrosine-sulfanilamide affinity chromatography and the compounds N-3-Methylbenzylidene-4-fluoroaniline (6b), N-4-Methylbenzylidene-4-fluoroaniline (6c),N-2-Methoxybenzylidene-4-fluoroaniline(6d)showed moderateactivity on hCAII in the range of IC50values.
📌 3 Key Takeaways
🎯
Objective & Hypothesis:In this study, some Schiff base derivatives (6a-f) were synthesized using a microwave method.
📊
Key Findings & Data:The synthesized compounds were characterized by 1D, 2D NMR and mass spectral data.
💡
Conclusion & Impact:Their inhibitory effects were studied on carbonic anhydrase isozymes (hCA I and II), purified from human erythrocyte cells by Sepharose-4B-L-tyrosine-sulfanilamide affinity chromatography and the compounds N-3-Methylbenzylidene-4-fluoroaniline (6b), N-4-Methylbenzylidene-4-fluoroaniline (6c),N-2-Methoxybenzylidene-4-fluoroaniline(6d)showed moderateactivity on hCAII in the range of IC50values.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters
Özet
In this study, some Schiff base derivatives (6a-f) were synthesized using a microwave method. The synthesized compounds were characterized by 1D, 2D NMR and mass spectral data. Their inhibitory effects were studied on carbonic anhydrase isozymes (hCA I and II), purified from human erythrocyte cells by Sepharose-4B-L-tyrosine-sulfanilamide affinity chromatography and the compounds N-3-Methylbenzylidene-4-fluoroaniline (6b), N-4-Methylbenzylidene-4-fluoroaniline (6c),N-2-Methoxybenzylidene-4-fluoroaniline(6d)showed moderateactivity on hCAII in the range of IC50values.
🔖
Cite This Article
ÇELİK, H., KUZU, M. (2019). Microvawe assisted synthesis of N-(methyl and methoxy) benzylidene-4-fluoroaniline derivatives and their carbonic anhydrase I and II inhibition properties. Organic Communications, Cilt: 12 - Sayı: 4, 210–216. https://ajindex.com/articles/288470
Schiff, H. Untersuchungen Uber Salicin Derivate. Ann. Chem.Pharm.1864, 131, 118-119. [2]da Silva, C.M.; da Silva, D.L.; Modolo, L.V.; Alves, R.B.; de Resende, M.A.; Martins, C.V.B.; de Fatima, A. Schiff bases: a short review of their antimicrobial activities. J. Adv. Res. 2011, 2, 1–8. [3]Dubey, S.N.; Vaid, B. K. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry.Rani, A., Kumar, M.; Khare, R.; Tuli,H.S.Schiff bases as an antimicrobial agent: A review. J. Biol.Chem. Sci. (JBCS). 2015, 1, 62-69. [4]Kajal, A.; Bala, S.; Kamboj, S.; Sharma, N.; Saini V. Schiff Bases: A Versatile Pharmacophore. J. Catal.2013,ArticleID893512, 14 pages. [5]Sztanke, K.; Maziarka, A.; Osinka,A.; Sztanke, M.An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorg. Med. Chem.2013,21, 3648-3666. [6]Murtaza,S.; Akhtar, M.S.; Kanwal, F.; Abbas, A.; Ashiq S.; Shamim, S.Synthesis and biological evaluation of Schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent.J. Saudi Chem. Soc.2017, 21, 359-372. [7]Pandeya, S. N.; Sriram, D. Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin Mannich bases. Acta. Pharm. Turc.1998, 40, 33-38. [8]Zhao, Q. J.; Song, Y.; Hu, H. G.; Yu, S. C.; Wu, Q. Y. Design, synthesis and antifungal activity of novel triazole derivatives. Chinese Chem. Lett. 2007, 18, 670-672. [9] [9] Kumar, S.; Niranjan, M. S.; Chaluvaraju, K. C.; Jamakhandi, C. M.; Kadadevar, D. Synthesis and Antimicrobial Study of Some Schiff Bases of Sulfonamides. J. Curr. Pharm. Res.2010, 1, 39-42. [10] Invidiata, F. P.; Furno, G.; Simoni, D.; Lampronti, I.; Musiu, C.; Milia, C.; Scintu, F.; La Colla, P. 3,6-Disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles: synthesis and evaluation for antimicrobial and antiviral activity. Farmaco 1997, 52, 259-261. [11] Chen, J.; Sun, X. Y.; Chai, K. Y.; Lee, J. S.; Song, M. S.; Quan, Z. S. Synthesis and anticonvulsant evaluation of 4-(4-alkoxylphenyl)-3-ethyl4H-1,2,4-triazoles as open-chain analogues of 7-alkoxyl-4,5dihydro[1,2,4]triazolo[4,3-a]quinolones. Bioorg. Med. Chem.2015, 15, 6775-6781. [12] Varma, M.; Pandeya, S. N.; Singh, K. N.; Stables J. P.Anticonvulsant activity of Schiff bases of isatin derivatives.Acta. Pharm.2004, 54, 49-56. [13] Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin Mannich bases. Eur. J. Med. Chem. 2000, 35, 249-255. [14] Akhtar, T.; H