Synthesis, characterization and antimicrobial activity of novel benzofuran- and thiophene-containing diketoxime derivatives

Demet Coskun, Seher Gur, Mehmet Fatih Coskun

Abstract


The aim of this study was the preparation of 1,1'-(2,5-thiophenediyl)bis[1-(2-benzofuranyl)methanone] (2), the corresponding diketoxime (3), and the ether and ester derivatives (4ae) of the diketoxime. These compounds were prepared in good yields. Minimum inhibitory concentrations (MIC) of the synthesized compounds 14 were determined against Salmonella enterica subsp. enterica serovar Typhimurium, Escherichia coli and Staphylococcus aureus. Among the synthesized com­pounds, 1 and 4e showed good activity against E. coli, S. enterica and S. aureus.


Keywords


bisbenzofuran; thiophene; diketoxime; antimicrobial activity

References


O. Oter, K. Ertekin, C, Kirilmis, M. Koca, M. Ahmedzade, Sens. Actuators, B 122 (2007) 450

F. Karatas, M. Koca, H. Kara, S. Servi, Eur. J. Med. Chem. 41 (2006) 664

R. W. Sabnis, D. W. Rangnekar, N. D. Sonawane, J. Heterocycl. Chem. 36 (1999) 333

A. M. Khalil, M. A. Berghot, E. Ghada, E. G. Abd, M. A. Gouda, Synth. Commun. 40 (2010) 1658

P. G. Costa Susana, E. Oliveira, C. Lodeiro, Tetrahedron Lett. 49 (2008) 5258

G. N. Schrauzer, Angew. Chem. Int. Ed. 15 (1976) 417

T. W. Thomas, A. E. Underhill, Chem. Soc. Rev. 1 (1972) 99

A. E. Underhill, D. M. Watkins, R. Pethig, Inorg. Nucl. Chem. Lett. 9 (1973) 1269

A. Chakravorty, Coord. Chem. Rev. 13 (1974) 1

K. Kurita, Polym. Degrad. Stab. 59 (1998) 117

N. K. Mathur, C. K. Narang, J. Chem. Educ. 67 (1990) 938

M. N. V. Ravi Kumar, React. Funct. Polym. 46 (2000) 1

A. Amalraj, R. Raghunathan, M. R. Sridevi Kumari, N. Raman, Bioorg. Med. Chem. 11 (2003) 407

I. G. Mobio, A. T. Soldatenkov, V. O. Federov, E. A. Ageev, N. D. Sergeeva, S. Lin, E. E. Stashenko, N. S. Prostakov, E. I. Andreeva, Khim.-Farm. Zh. 23 (1989) 421

R. V. Perumal, M. Adiraj, P. Shanmugapandiyan, Indian Drugs 38 (2001) 156

S. Balasubramanin, C. Ramalingan, G. Aridoss, S. Kabilan, Eur. J. Med. Chem. 40 (2005) 694

S. Balasubramanin, C. Ramalingan, G. Aridoss, P. Parthiban, S. Kabilan, Med. Chem. Res. 13 (2004) 297

C. Ramalingan, S. Balasubramanin, S. Kabilan, M. Vasudevan, Eur. J. Med. Chem. 39 (2004) 527

C. Ramalingan, S. Balasubramanin, S. Kabilan, M. Vasudevan, Med. Chem. Res. 12 (2003) 41

M. Srinivasan, S. Perumal, S. Selvaraj, Chem. Pharm. Bull. 54 (2006) 795

K. Narayanan, M. Shanmugan, S. Jothivel, S. Kabilan, Bioorg. Med. Chem. Lett. 22 (2012) 6602

J. V. Dijk, J. M. A. Zwagemakers, J. Med. Chem. 20 (1977) 1199

A. Bishnoi, S. Singh, A. K. Tiwari, A. Sethi, C. M. Tripathi, Med. Chem. 9 (2013) 45

A. Fravolini, F. Schiaffella, G. Orzalesi, R. Selleri. I. Volpato, Eur. J. Med. Chem. 13 (1978) 347

S. J. Burditt, P. B. Hamilton, Poultry Sci. 62 (1983) 2183

D. P. Jindal, R. Chattopadhaya, S. Guleria, R. Gupta, Eur. J. Med. Chem. 38 (2003) 1025

B. Premalatha, D. Bhakiaraj, B. Chellakili, M. Gopalakrishnan, J. Pharm. Res. 6 (2013) 730

N. O. Iskeleli, C. Kazak, C. Kirilmis, M. Koca, Acta Crystallogr., E 61 (2005) 1212

C. Kirilmis, M. Koca, A. Cukurovali, M. Ahmedzade, C. Kazaz, Molecules 10 (2005) 1399

Y. Miyahara, J. Heterocycl. Chem. 16 (1979) 1147

F. Yuksel, A. G. Gurek, M. Durmus, I. Gurol, V. Ahsen, E. Jeanneau, D. Luneau, Inorg. Chim. Acta 361 (2008) 2225

G. Massolini, M. L. Carmellino, A. Baruffini, Farmaco 49 (1994) 747

H. A. Dondas, R. Grigg, J. Markandu, T. Perrior, T. Suzuki, S. Thibault, W. A. Thomas, M. Thornton-Pett, Tetrahedron 58 (2002) 161

C. B. Li, H. Zhang, Y. Cui, S. M. Zhang, Z. Y. Zhao, M. C. K. Choi, A. S. C. Chan, Synth. Commun. 33 (2003) 543

A. B. Zaitsev, A. M., Vasil'tsov, E. Y. Schmidt, A. L. Mikhaleva, L. V. Morozova, A. V. Afonin, I. A. Ushakov, B. A. Trofimov, Tetrahedron 58 (2002) 10043

H. Sharghi, M. H. Sarvari, Synlett 1 (2001) 99

A. Gül, O. Bekaroglu, J. Chem. Soc. Dalton. Trans. 12 (1983) 2537

V. Ahsen, F. Gokceli, O. Bekaroglu, J. Chem. Soc. Dalton Trans. 8 (1987) 1827

A. Nakamura, A. Konishi, S. Otsuka, J. Chem. Soc. Dalton. Trans. 3 (1979) 488

M. S. Ma, R. J. Angelici, Inorg. Chem. 19 (1980) 363.




DOI: http://dx.doi.org/10.2298/JSC160517003C

Refbacks

  • There are currently no refbacks.


Copyright (c) 2017 J. Serb. Chem. Soc.

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

IMPACT FACTOR 0.970 (120 of 163 journals)
5 Year Impact Factor 0.997 (111 of 163 journals)