Nurten ALTANLAR, Süheyla ÖZBEY, AYHAN Gülgün KILCIGİL, Canan KUŞ

Synthesis and antimicrobial evaluation of some new 2-(2-(p-chlorophenyl) benzimidazol-1-yl methyl)-5-substituted amino-[1,2,4]-thiadiazoles

Some 2-(2-(p-chlorophenyl)benzimidazol-1-ylmethyl)-5-substituted amino-[1,3,4]-thiadiazoles were synthesized and their in vitro antimicrobial activities were tested against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans and Candida krusei. Compounds 1b and 12b which possess remarkable activity against C. albicans and marginal activity against C. krusei were found to be the most active compounds in this series. Single crystal X-ray diffraction analysis was performed for compound 8b.

PDF

___

1.A.E. Abdel-Rahman, A.M. Mahmoud, G.M. El-Naggar and H.A. El-Sherief, Pharmazie, 38, 589-590 (1983).
2.F.S.G. Soliman, S.M. Rida, E.A.M. Badawey and T. Kappe, Arch. Pharm., 317, 951-958 (1984).
3.R.A. Coburn, M.T. Clark, R.T. Evans and R.J. Genco, J. Med. Chem., 30, 205-208 (1987).
4.N.S. Habib, S. Abdel-Hamid, M and El-Hawash, Farmaco, 44, 1225-1232 (1989).
5.H. Göker, M. Tunçbilek, G. Ayhan and N. Altanlar, Farmaco, 53, 415-420 (1998).
6.G.A. Kılcıgil, M. Tunçbilek, N. Altanlar and H. Göker, Farmaco, 54, 562-565 (1999).
7.V.L. Khairnar, S.R. Lockhande, M.R. Patel and B.G. Khadse, Bull. Haffkine Inst. 8 (1980) 67-70: Chemical Abstract, 95, 203833h (1981).
8.L.I. Kruse, D.L. Ladd, P.B. Harrsch, F.L. McCabe, S.M. Mong, L. Faucette and R. Johnson, J. Med. Chem.,32, 409-417(1989).
9.I. Islam, E.B. Skibo, R.T. Dorr and D.S. Alberts, J. Med. Chem., 34, 2954-2961 (1991).
10.V.J. Habernickel, Drugs made in Germany, 35, 97 (1992).
11.T. Fukuda, Y. Morimoto, R. Iemura, T. Kawashima, G. Tsukamoto and K. Ito, Arzneim.-Forsch./Drug Res., 34, 801-805 (1984).
12.T. Fukuda, T. Saito, S. Tajima, K. Shimohara and K. Ito, Arzneim.-Forsch./Drug Res., 34, 805-810 (1984).
13.H. Nakano, T. Inoue, N. Kawasaki, H. Miyataka, H. Matsumoto, T. Taguchi, N. Inagaki, H. Nagai and T.Satoh, Chem. Pharm. Bull., 47, 1573-1578 (1999).
14.H. Nakano, T. Inoue, N. Kawasaki, H. Miyataka, H. Matsumoto, T. Taguchi, N. Inagaki, H. Nagai and T.Satoh, Bioorg. Med. Chem., 8, 373-380 (2000).
15.B. Can-Eke, M.O. Püsküllü, E. Buyukbingol and M. Iscan, Chemico-Biological Interactions, 113, 65-77 (1998).
16.S. Demirayak, U. Abu Mohsen and A.C. Karaburun, Eur. J. Med. Chem., 37, 255-260 (2002).
17.S. Ersan, S. Nacak, N. Noyanalpan and E. Yesilada, Arzneim.-Forsch./Drug Res., 47, 834-836 (1997).
18.D.H. Boschelli, D.T. Connor, D.A. Bornemeier, R.D. Dyer, J.A. Kennedy, P.J. Kuipers, G.C. Okonkwo, D.J.Schrier and CD. Wright, J. Med. Chem., 36, 1802- 1810 (1993).
19.G. Şahin, E. Palaska, P. Kelicen, R. Demirdamar and G. Altmok, Arzneim.-Forsch./Drug Res., 51, 478-484 (2001).
20.A. Tsotinis, A. Varvaresou, T. Calogeropoulou, T. Siatra-Papastaikoudi and A. Tiligada, Arzneim.-Forsch./Drug Res., 47, 307-310 (1997).
21.A.C.T. North, D.C. Phillips and F.S. Mathews, Açta Cryst., A24, 351-359 (1968).
22.G.M. Sheldrick, SHELXS97 Program for Crystal Structure Solution, University of Göttingen, Germany (1997).
23.G.M. Sheldrick, SHELXL97 Program for Crystal Structure Refinement, University of Göttingen,Germany (1997).
24.D.F. Sahm, J.A. Washington in Am. Soc. Microbiol., (Eds. A. Balowes, W.J. Hausler, K.L. Hermann and H.D. Shadomy) Washington 5tflEd. 1105-1116 (1991).
25.H.F. Ridley, R.G.W. Spickett and G.M. Timmis, J. Heterocyclic Chem., 2, 453-456 (1965).
26.H. Heaney and S.V. Ley, J. Chem. Soc. Perkin I, 499-500 (1973).
27.P.A.S. Smith, The Curtius Reaction. In: R. Adams, W.E. Bachmann, L.F. Fieser, J.R. Johnson and H.R.Snyder (Eds.) Organic Reactions, John Wiley & Sons, Inc. London: Chapman & Hall Limited Volume III,337-389 (1949).
28.T. Siatra-Papastaikoudi, A. Tsotinis, C.P. Raptopoulou, C. Sambani and H. Thomou, Eur. J. Med. Chem.,30, 107-114 (1995).
29.A. Varvaresou, T. Siatra-Papastaikoudi, A. Tsotinis, A. Tsantili-Kakoulidou and A. Vamvakides Farmaco,53, 320-326 (1998).
30.J.K. Johnson, ORTEP II. Report. ORNL-5138 Oak Ridge National Laboratory, Tennessee, USA (1976).