Microwave-Assisted Synthesis of Some Benzimidazole Derivatives Containing Imine Function

Benzimidazol modern ilaç keşfinde önemli bir farmakofordur. Birçok benzimidazole türevi yeni ilaç adayı bileşikler elde etmek amacıyla organik kimyacılar tarafından sentezlenmektedir. Bu çalışmada, imin fonksiyonu içeren yedi yeni benzimidazol türevi bileşik mikrodalga ışıma ve geleneksel yöntemle sentezlenmiştir. Elde edilen sonuçlara göre mikrodalga ısıtmanın geleneksel ısıtmaya göre verim, üründeki saflık ve zaman yönünde avantajları olduğu görülmüştür.

İmin Fonksiyonu İçeren BazıBenzimidazol Türevlerinin Mikrodalga Destekli Sentezi

Benzimidazole is an important pharmacophore in modern drug discovery. Many benzimidazole derivatives have been synthesized by organic chemists to obtain new drug candidates. In this work, seven new benzimidazole derivatives containing imine function have been synthesized by using microwave irradiation and conventional heating procedure. The results showed that microwave heating has many advantages on classical heating procedure on yields, purity of product and reduced times.

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  • Achar, K. C., K. M. Hosamani, and H. R. Seetharamareddy. 2010. In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives. European Journal of Medicinal Chemistry45 (5):2048-2054.
  • Barker, H. A., R. D. Smyth, H. Weissbach, J. I. Toohey, J. N. Ladd, and B. E. Volcani. 1960. Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5, 6-dimethylbenzimidazole. Journal of Biological Chemistry235:480-488.
  • Bekircan, O., E. Mentese, S. Ulker, and C. Kucuk. 2014. Synthesis of Some New 1,2,4-Triazole Derivatives Starting from 3-(4-Chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol with Anti-Lipase and Anti-Urease Activities. Archiv Der Pharmazie347 (6):387-397.
  • Chen, L. H., Y. S. Hsiao, G. S. Yellol, and C. M. Sun. 2011.Microwave Promoted Simple, Efficient and Regioselective Synthesis of Trisubstituted Imidazo[1,2-a]benzimidazoles on Soluble Support. Acs Combinatorial Science13 (2):112-119.
  • Dawood, K. M., N. M. Elwan, and B. F. Abdel-Wahab. 2011. Recent Advances on the Synthesis of Azoles, Azines and Azepines Fused to Benzimidazole. Arkivoc1:111-195.
  • Gowda, N. R. T., C. V. Kavitha, K. K. Chiruvella, O. Joy, K. S. Rangappa, and S. C. Raghavan. 2009. Synthesis and biological evaluation of novel 1-(4-methoxyphenethyl)-1H-benzimidazole-5-carboxylic acid derivatives and their precursors as antileukemic agents. Bioorganic & Medicinal Chemistry Letters19 (16):4594-4600.
  • Kahveci, B. 2005. Synthesis of 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones and their isatin-3-imine derivatives. Molecules10 (2):376-382.
  • Kahveci, B., F. Yilmaz, E. Mentese, M. Ozil, and S. A. Karaoglu. 2014. Microwave-Assisted Synthesis of Some Novel Benzimidazole Derivatives Containing Imine Function and Evaluation of Their Antimicrobial Activity. Journal of Heterocyclic Chemistry51 (4):982-990.
  • Kappe, C. O. 2004. Controlled microwave heating in modern organic synthesis. Angewandte Chemie-International Edition43 (46):6250-6284.
  • Kubo, K., K. Oda, T. Kaneko, H. Satoh, and A. Nohara. 1990. Synthesis of 2-[[(4-fluoroalkoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazoles as antiulcer agents. Chem Pharm Bull (Tokyo)38 (10):2853-2858.
  • Kulkarni, R. G., S. A. Laufer, C. V. M, and A. Garlapati. 2013. Synthesis, p38 kinase inhibitory and anti-inflammatory activity of new substituted benzimidazole derivatives. Med Chem9 (1):91-99.
  • Kumar, K., D. Awasthi, S. Y. Lee, I. Zanardi, B. Ruzsicska, S. Knudson, P. J. Tonge, R. A. Slayden, and I. Ojima. 2011. Novel trisubstituted benzimidazoles, targeting Mtb FtsZ, as a new class of antitubercular agents. Journal of Medicinal Chemistry54 (1):374-381.
  • Mentese, E., H. Bektas, S. Ulker, O. Bekircan, and B. Kahveci. 2014. Microwave-assisted synthesis of new benzimidazole derivatives with lipase inhibition activity. Journal of Enzyme Inhibition and Medicinal Chemistry29 (1):64-68.
  • Mentese, E., S. Ulker, and B. Kahveci. 2015. Synthesis and study of ?-glucosidaseinhibitory, antimicrobial and antioxidant activities of some benzimidazole derivatives containing triazole, thiadiazole, oxadiazole, and morpholine rings. Chemistry of Heterocyclic Compounds50 (12):1671-1682.
  • Patil, A., S. Ganguly, and S. Surana. 2008. Asystematic review of benzimidazole derivatives as an antiulcer agent. Rasayan J Chem1 (3):447-460.
  • Rashid, M., A. Husain, and R. Mishra. 2012. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents. European Journal of Medicinal Chemistry54:855-866.
  • Sarno, S., E. Papinutto, C. Franchin, J. Bain, M. Elliott, F. Meggio, Z. Kazimierczuk, A. Orzeszko, G. Zanotti, R. Battistutta, and L. A. Pinna. 2011. ATP Site-Directed Inhibitors of Protein Kinase CK2: An Update. Current Topics in Medicinal Chemistry11 (11):1340-1351.
  • Soni, L. K., T. Narsinghani, and A. Sethi. 2012. Anti-microbial benzimidazole derivatives: synthesis and in vitro biological evaluation. Medicinal Chemistry Research21 (12):4330-4334.
  • Tuncbilek, M., T. Kiper, and N. Altanlar. 2009. Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA. European Journal of Medicinal Chemistry44 (3):1024-1033.
  • Uchida, M., M. Chihiro, S. Morita, H. Yamashita, K. Yamasaki, T. Kanbe, Y. Yabuuchi, and K. Nakagawa. 1990. Synthesis and antiulcer activity of 4-substituted 8-[(2-benzimidazolyl)sulfinylmethyl]-1,2,3,4-tetrahydroquinoli nes and related compounds. Chem Pharm Bull (Tokyo)38 (6):1575-1586.
  • Varma, R. S. 2012. Microwave in organic synthesis. Weinheim: Wiley-VCH.
  • Velik, J., V. Baliharova, J. Fink-Gremmels, S. Bull, J. Lamka, and L. Skalova. 2004. Benzimidazole drugs and modulation of biotransformation enzymes. Research in Veterinary Science76 (2):95-108.
  • Wang, P., G. J. Zheng, Y. P. Wang, X. J. Wang, H. G. Wei, and W. S. Xiang. 2012. Highly practical and cost-efficient synthesis of telmisartan: an antihypertensive drug. Tetrahedron68 (11):2509-2512.
  • Yilmaz, F., E. Mentese, N. Karaali, and B. Kahveci. 2013. Microwave-assisted synthesis of some 5(6)-nitro-1H-benzimidazoles and their hydrazide derivatives. Bulletin of the Chemical Society of Ethiopia27 (2):265-271.