Therefore,2acan be a pro-drug as an anticancer, antibacterial, and antifungal agent.
📌 3 Key Takeaways
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Objective & Hypothesis:A series of novel positional oximes (2a{2d),O-methyl oxime ethers (3a{3d), andO-benzyl oxime ethers(4a{4d) were synthesized in high yields starting from their corresponding methyl 3-, 4-, 6-, and 13-keto tetradecanoates.The synthesized compounds were characterized by1H NMR,13C NMR, FT-IR, mass, and elemental analyses fortheir structures and (E)/(Z) isomerizations.
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Key Findings & Data:The relationship between the structure and the mentioned biological activities was discussed.Compound2ashowed good antibacterial activity against ve types of bacteria.
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Conclusion & Impact:Therefore,2acan be a pro-drug as an anticancer, antibacterial, and antifungal agent.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters
Abstract
A series of novel positional oximes (2a{2d),O-methyl oxime ethers (3a{3d), andO-benzyl oxime ethers(4a{4d) were synthesized in high yields starting from their corresponding methyl 3-, 4-, 6-, and 13-keto tetradecanoates.The synthesized compounds were characterized by1H NMR,13C NMR, FT-IR, mass, and elemental analyses fortheir structures and (E)/(Z) isomerizations. Their DNA binding abilities were investigated in vitro by agarose gelelectrophoresis. The antibacterial and antifungal activities were tested also in vitro against eleven bacterial strainsand three fungal strains. The relationship between the structure and the mentioned biological activities was discussed.Compound2ashowed good antibacterial activity against ve types of bacteria. Compounds2b,2c,2d, and4dwereeffective against several microorganisms. Among these,2ashowed the best DNA binding, antibacterial, and antifungalactivities. Therefore,2acan be a pro-drug as an anticancer, antibacterial, and antifungal agent.
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Cite This Article
AÇIK, L., AYDIN, B., ARSLAN, L., YUSUFOĞLU, A. S., KÜÇÜK, H. B. (2022). Synthesis, (E)/(Z)-isomerization, and DNA binding, antibacterial, and antifungalactivities of novel oximes andO-substituted oxime ethers. Turkish Journal of Chemistry, Cilt: 40 - Sayı: 5, 816–829. https://ajindex.com/articles/602000
Aakeroy, C. B.; Salmon, D. J.; Smith, M. M.; Desper, J.Cryst. Eng. Comm.2009,11, 439-444. 2.Aakeroy, C. B.; Fasulo, M.; Schultheiss, N.; Desper, J.; Moore, C.J. Am. Chem. Soc.2007,129, 13772-13773. 3.Scarso, A.; Pellizzaro, L.; Lucchi, O. D.; Linden, A.; Fabris, F.Angew. Chem., Int. Ed.2007,46, 4972-4975. 4.Rappoport, Z.; Liebman, J. F.The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, Part 1; PataiSeries: The Chemistry of Functional Groups; John Wiley & Sons, Ltd.: Chichester, UK, 2009, pp. 609-612. 5.Eyer, P. A.; Worek, F. InChemical Warfare Agents: Toxicology and Treatment, 2nd ed.; Marrs, T. C., Maynard,R. L., Sidell, F. R., Eds.; John Wiley & Sons, Ltd.: Chichester, UK, 2007, pp. 304-310. 6.Brain, G. E.; Forrest, K. A.; Hunt, E.; Shillingford, C.; Wilson, M. J.J. Antibiot.1989,42, 1817-1822. 7.Chern, J. H.; Lee, C. C.; Chang, C. S.; Lee, Y. C.; Tai, C. L.; Lin, Y. T.; Shia, K. S.; Lee, C. Y.; Shih S. R.Bioorg.Med. Chem. Lett.2004,14, 5051-5056. 8.Emami, S.; Falahati, M.; Banifatemi, A.; Amanlou, M.; Sha ee, A.Bioorg. Med. Chem.2004,12, 3971-3976. 9.Jindal, D. P.; Chattopadhaya, R.; Guleria, S.; Gupta, R.Eur. J. Med. Chem.2003,38, 1025-1034. 10.Tu, S.; Xie, Y. Q.; Gui, S. Z.; Ye, L. Y.; Huang, Z. L.; Huang, Y. B.; Che, L. M.Bioorg. Med. Chem. Lett.2014,24, 2173-2176. 11.Karakurt, A.; Dalkara, S.;Ozalp, M.;Ozbey, S.; Kendi, E.; Stables, J. P.Eur. J. Med. Chem.2001,36, 421-433. 12.Prabhu, V. A.; Brown, R. G.; Delgado, N. J.J. Pharm. Sci.1981,70, 558-562. 13.Eyer, P.Toxicol Rev.2003,22, 165-190. 14.Eddleston, M.; Szinics, L.; Eyer, P.; Buckley, N.Q. J. Med.2002,95, 275-283. 15.Wilhelm, C. M.; Snider, T. H.; Babin, M. C.; Jett, D. A.; Platoff Jr., G. E.; Yeung D. T.Toxicol. Appl. Pharm.2014,281, 254-265. 16.Ichimaru, Y.; Saito, H.; Uchiyama, T.; Metori, K.; Tabata, K.; Suzuki, T.; Miyairi, S.Bioorg. Med. Chem. Lett.2015,25, 1403-1406. 17.Wang, R.; Zhang, X.; Song, H.; Zhou, S.; Li, S.Bioorg. Med. Chem. Lett.2014,24, 4304-4307. 18.Kim, Y.; Hong, Y. D.; Joo, Y. H.; Woo, B. Y.; Kim, S. Y.; Koh, H. J.; Park, M.; Byoun, K. H.; Shin, S. S.Bioorg.Med. Chem. Lett.2014,24, 2807-2810. 19.Surkau, G.; Bohm, K. J.; Muller, K.; Prinz, H.Eur. J. Med. Chem.2010,45, 3354-3364. 20.Yang, Y.; Wang, X.; Zhu, Q.; Gong, G.; Luo, D.; Jiang, A.; Yang, L.; Xu, Y.Bioorg. Med. Chem. Lett.2014,24,1851-1855. 21.Liu, S.; Ji, D.; Yang, Y.; Zhen, X.; Tian X.; Han, J.Lett. Org. Chem.2009,6, 156-158. 22.Noverges, B.; Simon, M. M.; Asensio, G.Adv. Synth. Catal.2015,357, 4