Handan ALTINTAŞ, Öznur ATEŞ, Seher BİRTEKSÖZ, Gülten ÖTÜK

Synthesis of Mannich Bases of Some 2,5-Disubstituted 4-Thiazolidinones and Evaluation of Their Antimicrobial Activities

4-Carbethoxymethyl-2-[(a -chloropropionyl/a -bromobutyryl/a-chloro-(a-phenyl)acetyl)amino]thiazoles (2a-c) were synthesized by the reaction of 4-carbethoxymethyl-2-aminothiazole (1) with a-chloropropionyl chloride, a-bromobutyryl bromide and a-chloro-a -phenylacetyl chloride, respectively, which were then refluxed with ammonium thiocyanate to obtain 5-substituted 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones (3a-c). 3a-c were stirred with formaldehyde and various secondary amines to gain 15 novel compounds with the structure 5-substituted 5-(N,N-disubstituted aminomethyl)-2-[(4-carbethoxymethylthiazol-2-yl)imino]-4- thiazolidinones (4a-o). The antibacterial activities of the compounds against S. aureus ATCC 6538, S. epidermidis ATCC 12228, E. coli ATCC 8739, K. pneumoniae ATCC 4352, P. aeruginosa ATCC 1539, S. typhi, Sh. flexneri and Pr. mirabilis ATCC 14153 were tested using disk diffusion, while the antifungal activities of the compounds against M. gypseum NCPF-580, M. canis, T. mentagrophytes, T. rubrum and C. albicans ATCC 10231 were tested using microdilution.

Anahtar Kelimeler:

2, 5-Disubstituted 4-thiazolidinones, synthesis, Mannich bases, antimicrobial activity

Synthesis of Mannich Bases of Some 2,5-Disubstituted 4-Thiazolidinones and Evaluation of Their Antimicrobial Activities

Keywords:

2, 5-Disubstituted 4-thiazolidinones, synthesis, Mannich bases, antimicrobial activity,

PDF

___

B.K. Garnaik and R.K. Behera, Indian J. Chem. Sect. B 27B(12), 1157-1158 (1988).
E.V. Vladzimirskaya, O.T. Novikevich and O.G. Demchuk, Farm. Zh. (Kiev) (6), 67-71 (1991).
R. Lakhan and R. L. Singh, J. Agric. Food Chem. 39 (3), 580-583 (1991).
S.A.H. El-Feky and Z.K. Abd El-Samii, Arch. Pharm. (Weinheim) 324, 381-383 (1991).
S.A.H. El-Feky, Pharmazie 48, 894-896 (1993).
S. Grasso, A. Chimirri, P. Monforte, G. Fenech and M. Zappala, Farmaco 41(12), 713-721 (1986).
M. Kupinic, M. Medic-Saric, M. Movrin and D. Maysinger, J. Pharm. Sci. 68(4), 459-462 (1979).
R.W. Daisley and V.K. Shah, J. Pharm. Sci. 73(3), 407-408 (1984).
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Arzneim.-Forsch./Drug Res. 50(I), 55-59 (2000).
S.N. Pandeya, D. Sriram, G. Nath and E. De Clercq, J. Pharm. Sci. 9, 25-31 (1999).
O. Ate¸s, H. Altınta¸s and G. ¨Ot¨uk, Arzneim.-Forsch./Drug Res. 50(1), 569-575 (2000). ¨
S.M. Rida, A.M. Farghaly and F.A. Ashour, Pharmazie 34, 214-216 (1979).
J. Sahu, S.S. Meher, S. Naik and A. Nayak, J. Indian Chem. Soc. 62, 71-73 (1985).
V.G. Zubenko, Farm. Zh. (Kiev) 26(5), 11-19 (1971).
N.J. Gaikwad and K. Shah, Indian Drugs 26, 341-342 (1989). Ref. CA 111, 167144x (1989).
K.C. Kauer, U.S. Patent 2, 780,631 (1957). Ref. CA 51, 10587e (1957).
Z. Cesur, Pharmazie 42(11), 716-717 (1987).
A. Kocabalkanlı and ¨O. Ate¸s and G. ¨Ot¨uk, Arch. Pharm. Pharm. Med. Chem. 334, 35-39 (2001).
National Committee for Clinical Laboratory Standards. (2000).
National Committee for Clinical Laboratory Standards. (1997).
National Committee for Clinical Laboratory Standards. (1998).
B. Fernandez-Torres, F.J. Cabanes, A. Carilla-Munoz, A. Esteban, I. Inza, L. Abarca and J. Guarro, J. Clinical
Microbiol. 40, 3999-4003 (2002). 23. B. Fernandez-Torres, A.J. Carillo, E. Martin, A.D. Palacio, M.K. Moore, A. Valverde, M. Serrano and J.
Guarro, Antimicrob. Agents Chemother. 45, 2524-2528 (2001). 24. A.K. Gupta and Y. Kohli, Brit. J. of Dermatol. 149, 296-305 (2003). 25. A. Espinel-Ingroff, C.W. Kigh, T.M. Kerkering, R.A. Famthing, K. Bartizal, J.N. Galgiani, K. Villareal, M.A.
Pfaller, T. Gerarden, M.G. Rinaldi and A. Fathergill, J. Clin. Microbiol. 30, 3138-3145 (1992). 26. J.L. Rodriguez-Tudela, J. Berenguer, J.V. Martinez-Suarez and R. Sanchez, Antimicrob. Agents Chemother.
, 1998-2003 (1996). 27. G. C¸ apan and N. Ergen¸c, Sci. Pharm. 61, 243-250 (1993). 28. S. Singh, G.P. Gupta and K. Shanker, Indian J. Chem. Sect. B, 24B(10), 1094-1097 (1985).