H. Ali DÖNDAŞ, Yahya NURAL, Nizami DURAN

Synthesis, Crystal Structure and Antifungal/Antibacterial Activity of Some Novel Highly Functionalized Benzoylaminocarbothioyl Pyrrolidines

A series of novel highly functionalized benzoylaminocarbothioyl pyrrolidines were prepared from benzoylisothiocyanate and substituted pyrrolidines in excellent yield. The crystal structure of the novel 1-benzoylaminocarbothioyl-5-(naphthyl)- pyrrolidine-2,3,4-tricarboxylicacid trimethyl ester (3a) was determined by X-ray crystal structure analysis. The synthesized compounds were characterized and screened for their in vitro antibacterial and antifungal activities and toxicity. The prepared compounds were tested against the standard strains: Escherichia coli (ATCC 25922), Enterobacter cloacae (ATCC 13047), Enterococcus faecalis (ATCC 29212), Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (ATCC 29213) and Staphylococcus epidermidis (ATCC 12228) and the yeasts Candida albicans (ATCC 90028), Candida krusei (ATCC 6258), Candida parapsilosis (ATCC 22019), Candida tropicalis (ATCC 22019) and Candida glabrata (ATCC 32554).

Anahtar Kelimeler:

Pyrrolidine derivatives, aminocarbothioyl derivatives, bioactivity, antibacterial activity, antifungal activity, toxicity

Synthesis, Crystal Structure and Antifungal/Antibacterial Activity of Some Novel Highly Functionalized Benzoylaminocarbothioyl Pyrrolidines

Keywords:

Pyrrolidine derivatives, aminocarbothioyl derivatives, bioactivity, antibacterial activity, antifungal activity, toxicity,

PDF

___

E. Rodr´ıguez-Fern´andez, J.L. Manzano, J.J. Benito, R. Hermosa, E. Monte and J.J. Criado. J. Inorg. Biochem. Rev., 99, 1558-1572 (2005).
J.J. Criado, E. Rodr´ıguez-Fern´andez, E. Garc´ıa, M.R. Hermosa and E. Monte, J. Inorg. Biochem., 69, 119 (1998).
R. Del Campo, J.J. Criado, E. Garc´ıa, M.R. Hermosa, A.Jim´enez-S´anchez, J.L. Manzano, E. Monte, E. Rodr´ıguez-Fern´andez and F. Sanz, J. Inorg. Biochem., 89, 74-82 (2002).
E. Rodr´ıguez-Fern´andez, E. Garc´ıa, M.R. Hermosa, A. Jim´enez-S´anchez, M.M. S´anchez, E. Monte and J.J. Criado. J. Inorg. Biochem., 75, 181-188 (1999).
R. Del Campo, J.J. Criado, R. Gheorghe, F.J. Gonz´alez, M.R. Hermosa, F. Sanz, J.L. Manzano, E. Monte and E. Rodr´ıguez-Fern´andez, J. Inorg. Biochem., 98, 1307-1314 (2004).
D.A. Pennington, P.N. Horton, M.B. Hursthouse, M. Bochmann and S.J. Lancaster, Polyhedron, 24, 151-156 (2005).
C. Sacht, M.S. Datt, S. Otto and A. Roodt, J. Chem. Soc. Dalton Trans, 5, 727-733 (2000).
R. Nicolae and B. Lucica, Revista de Chimie. 53, 758-760 (2002).
K.R. Koch, Coordin. Chem. Rev., 216, 473-488 (2001).
L. Beyer, E. Hoyer, H. Hartman and J. Liebscher, Z. Chem. 21, 81-91 (1981).
P. M¨uhl, K. Gloe, F. Dietze, E. Hoyer and L. Beyer, Z. Chem. 26, 81-94 (1986).
L. Beyer, E. Hoyer, E. Hennig, H. Kirmse, H. Hartman and J. Liebscher, Fresen. J. Anal. Chem. (Leipzig). , 829-839 (1975).
M. Guttmann, K.H. Lubert and L. Beyer, Fresenius J. Anal. Chem. 356, 263-266 (1996).
X. Shen, X. Shi, B. Kang, Y. Tong, Y. Liu, L. Gu, Q. Liu and Y. Huang, Polyhedron, 18, 33-37 (1998).
J.C. Brindley, J.M. Caldwell, G.D. Meakins, S.J. Plackett and J.P. Price, J. Chem. Perkin Trans. 1, 1153- (1987).
A. Mohamadou, I. Dechamps-Olivier and J.P. Barbier, Polyhedron, 13, 3277-3283 (1994).
I. Dechamps-Olivier, E. Guillion, A. Mohamadou and J.P. Barbier, Polyhedron, 15, 3617-3622 (1996).
M. Schuster, B. Kugler and K.H. K¨onig, J. Anal. Chem. 338, 717-720 (1990).
M. Schuster, J. Anal. Chem. 342, 791-794 (1992).
K.H. K¨onig, M. Schuster, G. Schneeweis and B. Steinbrech, Fresenius Zeit. Anal. Chem. 319, 66-69 (1984).
K.H. K¨onig, M. Schuster, G. Schneeweis, B. Steinbrech and R. Schlodder, Fresenius Zeit. Anal. Chem. , 457-460 (1985).
P. Vest, M. Schuster and K.H. K¨onig, Fresen. J. Anal. Chem. 335, 759-763 (1989).
P. Vest, M. Schuster and K.H. K¨onig, Fresen. J. Anal. Chem. 339, 142-144 (1991).
P. Vest, M. Schuster and K.H. K¨onig, Fresen. J. Anal. Chem. 341, 566-568 (1991).
M. Schuster and E. Unterreitmeier, Fresen. J. Anal. Chem. 346, 630-633 (1993).
M. Schuster and M. Sandor, Fresen. J. Anal. Chem. 356, 326-330 (1996).
M. Schuster and E. Unterreitmeier, Anal. Chim. Acta. 309, 339-344 (1995).
M. Schuster and M. Schwarzer, Anal. Chim. Acta. 328, 1-11 (1996).
R. Grigg, Chem Soc. Rev. 16, 89-121 (1987).
H.A. D¨onda¸s, PhD thesis, The University of Leeds, England, 1997.
H.A. D¨onda¸s, R. Grigg and C. Killner, Tetrahedron, 59, 8481-8487 (2003).
A.D. Barr, R. Grigg, N.H.Q. Gunarate, J. Kemp, P. McMeekin and V. Sridharan, Tetrahedron, 44, 557-570 (1988).
H.A. D¨onda¸s. R. Grigg and M. Thornton-Pett, Tetrahedron, 52, 13455-13466 (1996).
H.A. D¨onda¸s and S. Sonmez, Heterocyl. Commun., 9, 23-30 (2003).
H.A. D¨onda¸s, C.W.G. Fiswick, R. Grigg and C. Killner, Tetrahedron, 60, 3473-3485 (2004).
R. Grigg, M. Thornton-Pett, J. Xu and L.H. Xu, Tetrahedron, 55, 13841-13866 (1999).
H.A. D¨onda¸s, R. Grigg, W.S. MacLachan, D.T. MacPherson, J. Markandu, V. Sridharan and S. Suganthan, Tetrahedron Letters, 55, 967-970 (2000).
H.A. D¨onda¸s, J. Duraisingham, R. Grigg, W.S. MacLaclan, D.T. MacPherson, M. Thornton-Pett, V. Sridharan and S. Suganthan, Tetrahedron, 56, 4063-4070 (2003).
H.A D¨onda¸s and ¨O. Altınba¸s, Heterocyl. Commun., 10, 167-174 (2004).
R. Frank, H. Davis, S. Drake and J. McPherson, J. Am. Chem. Soc. 66, 1509-1515 (1944).
H.A. D¨onda¸s, C.W.G. Fishwick, X. Gai, R. Grigg, C. Kilner, N. Dumrongchai, C. Polysuk and V. Sridharan, Angew. Chem. Int. Ed. 44, 7570-7574 (2005).
P. Blaney, R. Grigg, Z. Rankovich, M. Thornton-Pett and J. Xu, Tetrahedron, 58, 1719-1737 (2002).
L. Beyer, J.J. Criado, E. Garci´a, F. Lessmann, M. Medarde, R. Richter and E. Rodr´ıguez, Tetrahedron, 52, 6240 (1996).
C.J. Alexopoulos and C.W. Mims, Introductory Mycology, 3rd ed. Wiley, NY, 1979.
M.A. Ghannoum and L.B. Rice, Clin. Microbiol. Rev. 12, 501-517 (1999).
F.G. Burlesson, T.M Chambers and D.L. Wedbrauk, “Cytopathic Eﬀect Inh. Bioassay, In Virology A Laboratory Manual”, Academic Press, ING., New York, 1992.
National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal sus- ceptibility testing of yeasts. Approved standard NCCLS document M27-A. National Committee for Clinical Laboratory Standards, Wayne, Pa., (2002).
E. Borenfreund and J.A. Puerner, J. Tissue Cult. Meth., 9, 7-9 (1984).
E. Borenfreund and J.A. Puerner, Toxicol. Lett. 24, 119-124 (1985).