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İmin Fonksiyonu İçeren Bazı Benzimidazol Türevlerinin Mikrodalga Destekli Sentezi

Year 2015, Volume: 2 Issue: 4, 123 - 127, 19.06.2015

Gülay Akyüz Fatih Yılmaz , Emre Menteşe

Abstract

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.

Keywords

Benzimidazol Schiff bazı Mikrodalga Işıma İmin fonksiyonu

References

  • 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 Chemistry 45 (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 Chemistry 235:480-488.
  • 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 Pharmazie 347 (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 Science 13 (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. Arkivoc 1:111-195.
  • 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 Letters 19 (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. Molecules 10 (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 Chemistry 51 (4):982-990.
  • Kappe, C. O. 2004. Controlled microwave heating in modern organic synthesis. Angewandte Chemie-International Edition 43 (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 Chem 9 (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 Chemistry 54 (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 Chemistry 29 (1):64-68.
  • Mentese, E., S. Ulker, and B. Kahveci. 2015. Synthesis and study of α-glucosidaseinhibitory, antimicrobial and antioxidant activities of some benzimidazole derivatives containing triazole, thiadiazole, oxadiazole, and morpholine rings. Chemistry of Heterocyclic Compounds 50 (12):1671-1682.
  • Patil, A., S. Ganguly, and S. Surana. 2008. Asystematic review of benzimidazole derivatives as an antiulcer agent. Rasayan J Chem 1 (3):447-460.
  • Rashid, M., A. Husain, and R. Mishra. 2012. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents. European Journal of Medicinal Chemistry 54:855-866.
  • 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 Chemistry 11 (11):1340-1351.
  • Soni, L. K., T. Narsinghani, and A. Sethi. 2012. Anti-microbial benzimidazole derivatives: synthesis and in vitro biological evaluation. Medicinal Chemistry Research 21 (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 Chemistry 44 (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 Science 76 (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. Tetrahedron 68 (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 Ethiopia 27 (2):265-271.

Microwave-Assisted Synthesis of Some Benzimidazole Derivatives Containing Imine Function

Year 2015, Volume: 2 Issue: 4, 123 - 127, 19.06.2015

Gülay Akyüz Fatih Yılmaz , Emre Menteşe

Abstract

Benzimidazole is an important pharmacophore in modern drug discovery. Many benzimidazole derivatives have been synthesized by organic chemist 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.

Keywords

Benzimidazole Schiff base Microwave irradiation Imine function

References

  • 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 Chemistry 45 (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 Chemistry 235:480-488.
  • 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 Pharmazie 347 (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 Science 13 (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. Arkivoc 1:111-195.
  • 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 Letters 19 (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. Molecules 10 (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 Chemistry 51 (4):982-990.
  • Kappe, C. O. 2004. Controlled microwave heating in modern organic synthesis. Angewandte Chemie-International Edition 43 (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 Chem 9 (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 Chemistry 54 (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 Chemistry 29 (1):64-68.
  • Mentese, E., S. Ulker, and B. Kahveci. 2015. Synthesis and study of α-glucosidaseinhibitory, antimicrobial and antioxidant activities of some benzimidazole derivatives containing triazole, thiadiazole, oxadiazole, and morpholine rings. Chemistry of Heterocyclic Compounds 50 (12):1671-1682.
  • Patil, A., S. Ganguly, and S. Surana. 2008. Asystematic review of benzimidazole derivatives as an antiulcer agent. Rasayan J Chem 1 (3):447-460.
  • Rashid, M., A. Husain, and R. Mishra. 2012. Synthesis of benzimidazoles bearing oxadiazole nucleus as anticancer agents. European Journal of Medicinal Chemistry 54:855-866.
  • 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 Chemistry 11 (11):1340-1351.
  • Soni, L. K., T. Narsinghani, and A. Sethi. 2012. Anti-microbial benzimidazole derivatives: synthesis and in vitro biological evaluation. Medicinal Chemistry Research 21 (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 Chemistry 44 (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 Science 76 (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. Tetrahedron 68 (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 Ethiopia 27 (2):265-271.
There are 24 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Gülay Akyüz This is me

Fatih Yılmaz

Emre Menteşe

Publication Date June 19, 2015
Published in Issue Year 2015 Volume: 2 Issue: 4

Cite

APA Akyüz, G., Yılmaz, F., & Menteşe, E. (2015). Microwave-Assisted Synthesis of Some Benzimidazole Derivatives Containing Imine Function. Avrupa Bilim Ve Teknoloji Dergisi, 2(4), 123-127.
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