Synthesis and in Vitro Antimicrobial and Cytotoxicity Activities of 2-[(2-nitro-1-phenylalkyl)thio]benzoic Acid Derivatives

In this research 14 compounds were tested for their antimicrobial activity. The synthesis of 7 compounds corresponding to 2-[(2-nitro-1-phenyl-propyl)thio]benzoic acids 4 has not been reported before and 7 compounds corresponding to 2-[(2-nitro-1-phenyl-ethyl) thio]benzoic acid 3 were reported by our research group. The antibacterial activity of the title compounds was evaluated by 2 Gram (+) (Staphylococcus aureus, Bacillus subtilis) and 2 Gram (-)(Pseudomonas aeruginosa, Escherichia coli) microorganisms. The antifungal activity of the compounds was also determined against yeast-like fungi (Candida albicans, C. krusei). For antibacterial activity, ampicillin and for antifungal activity, fluconazole and ketoconazole have been used as reference compounds. All of the 2-[(2-nitro-1-phenyl-ethyl)thio]benzoic acid 3 derivatives were more active than the reference compound ketoconazole in the antifungal activity test. The title compounds were also screened by consecutive dilution to explore their toxicity to a Vero cell line. Except for 3d and 3e all of the compounds 3 exhibited lower toxicity than ketoconazole.

Synthesis and in Vitro Antimicrobial and Cytotoxicity Activities of 2-[(2-nitro-1-phenylalkyl)thio]benzoic Acid Derivatives

In this research 14 compounds were tested for their antimicrobial activity. The synthesis of 7 compounds corresponding to 2-[(2-nitro-1-phenyl-propyl)thio]benzoic acids 4 has not been reported before and 7 compounds corresponding to 2-[(2-nitro-1-phenyl-ethyl) thio]benzoic acid 3 were reported by our research group. The antibacterial activity of the title compounds was evaluated by 2 Gram (+) (Staphylococcus aureus, Bacillus subtilis) and 2 Gram (-)(Pseudomonas aeruginosa, Escherichia coli) microorganisms. The antifungal activity of the compounds was also determined against yeast-like fungi (Candida albicans, C. krusei). For antibacterial activity, ampicillin and for antifungal activity, fluconazole and ketoconazole have been used as reference compounds. All of the 2-[(2-nitro-1-phenyl-ethyl)thio]benzoic acid 3 derivatives were more active than the reference compound ketoconazole in the antifungal activity test. The title compounds were also screened by consecutive dilution to explore their toxicity to a Vero cell line. Except for 3d and 3e all of the compounds 3 exhibited lower toxicity than ketoconazole.

___

  • F. Sch¨ofer and M. Schooh, Arzneimmittel-Forsch., 8, 374-376 (1948).
  • O. Schales and H.A. Grafee, J. Am. Chem. Soc. 74, 4486-4490 (1952).
  • A.D. Xorge and S.S. Jorge, J. Am. Chem. Soc. 75, 4581-4582 (1953).
  • L.F. Cason, US, 3,376,340(CL. 260-562)02 Apr. 1968, Appl. 23 Nov. 1965; 3pp. Ref. Chem Abst. 70, 3507b (1968).
  • P. Messinger, Arch. Pharm. (Weinheim, Ger) 30(6), 458-462 (1973).
  • T.A. Lies and J.W. Clapp., US 4, 038, 288 (Cl. 260-329S;C07D333/00), 26 Jul 1977, Appl 127, 825, 24 Mr
  • ; 16pp. Ref. Chem. Abst., 87 167565w (1977).
  • E. Ber¸cin, M. G¨ok¸ce, U. Abbaso˘glu and N. Noyanalpan, J. Fac. Pharm. Gazi, 12(2) 117-128 (1995).
  • E. Ber¸cin, M. G¨ok¸ce, B. ¨Oz¸celik, M. Yurtsever and N. Noyanalpan, J. Fac. Pharm. Gazi, 12(2) 173-187 (1995).
  • E. Ber¸cin and M. G¨ok¸ce, J. Fac. Pharm. Gazi, 13(1) 33-44 (1996).
  • E. Ber¸cin and S. ¨Ozg¨u¸cl¨u, J. Fac. Pharm. Gazi, 13(2) 133-142 (1996).
  • S. ¨Ozg¨u¸cl¨u, M. G¨ok¸ce, E. Ber¸cin, B. ¨Oz¸celik, T. Karao˘glu and N. Noyanalpan, Archiv Der Pharmazie, submitted.
  • M. G¨ok¸ce, B. ¨Oz¸celik, G. Bakır, T. Karao˘glu, E. Ber¸cin, and N. Noyanalpan, Arzneim-Forsch., in press.
  • V. Climesova, J. Koci, M. Pour, J. Stachel, K. Waisser and J. Kaustova, Eur. J. Pharm. Chem,, 37, 409-418 (2002).
  • J. Valdez, R. Cedillo, A. Hernandez-Campos, L.Yepez, F. Hernandez-Luis, G. Navarrete-Vazquez, A.Tapia, R. Cortes, M.Hernandez and R.Castillo, Bioorganic & Medicinal Chem. Letters, 12, 2221-2224 (2002).
  • T.C. K¨uhler., M. Swanson, B. Christenson, C.A. Klintenberg, B. Lamm, J. Fagerhag, G. Roberto, M. ¨Olwegard- Halvarsson, V. Shcherbuchin, T. Elebring and J.E. Sj¨ostr¨om, J. Med. Chem., 45, 4282-4299 (2002).
  • M. Andrzejewska, L. Yepez-Mulia, A. Tapia, R. Cedillo-Rivera, A.E. Laudy, B.J. Starosciak and Z. Kazimier- czuk, Eur. J. Pharm. Chem., 21, 323-329 (2004).
  • M. G¨ok¸ce, E. Ber¸cin, J. Fac. Pharm. Gazi, 13(2) 153-160 (1996).
  • D.E. Worral, Organic Synthesis, Coll. Volume 1, 413-415 (1941).
  • M. Koremura, H. Oku, T. Shono, T. Nakanishi, Takamine Kenkyusho Nempo, 13, 198-204 (1961).
  • a) C. Thornsberry, J. Anhalt, A.L. Barry, L. Cotton, E.H. Gerlach¨o, R.N. Jones, R.A. Norton, NCCLS, 5, b) National Committee for Clinical Laboratory Standards: method for broth dilution antifungal susceptibility testing yeast; approved standard, M27-A, 15, NCCLS, 10, VA Medical Center, Tuscon (1996).
  • W.E. Walker, B.A. Waisbren, R.R. Martins, G.E. Bataiyas, Am. Clin. Path. 56, 687-692 (1971).
  • A. Hensten-Pettersen, Int. End. J., 21, 89-99 (1988).
  • J.M.T. Hamilton-Miller, International Journal of Antimicrobial Agents, 23, 209-212 (2004).
  • M.E. Jones, J.A. Karlowsky, D.C.Draghi, C. Thornsberry, D.F. Sahm and D. Nathwani, International Journal of Antimicrobial Agents, 23, 240-246 (2004).
  • G. Fadda, T. Spanu, F. Ardito , C. Taddei , R. Santangelo , A. Siddu, D. Ciccaglione, International Journal of Antimicrobial Agents, 23, 254-261 (2004).
  • Z. Wang, T. Jian , L.T. Phan and Y.S. Or, Bioorganic & Medicinal Chemistry Letters, 14, 519-521 (2004)
  • J.A. Dromigny, B. Ndoye, E.A. Macondo, P. Nabeth, T. Siby and J. D.Perrier-Gros-Claude, Diagnostic Microbiology and Infectious Disease, 47, 595-600 (2003).
  • A.D. Russell, The Lancet Infectious Diseases, 3, 794-803 (2003).
  • H. Hanaki, Y. Yamaguchi, S. Nomura, I Haraga, A. Nagayama, K. Sunakawa, International Journal of Antimicrobial Agents, 23, 1-5 (2004).
  • H.V. Melckebeke, C. Vreuls, P. Gans, P. Filee, G. Liabres, B. Joris, and J.P. Simorre, Journal of Molecular Biology, 333, 711-720 (2003).
  • T. Korpimaki, J. Kurittu, M. Karp, Journal of Microbiological Methods, 53, 37-42 (2003).
  • L.E. Nunez, C. Mendez, A.F. Brana, G. Blanco and J.A. Salas, Chemistry & Biology, 10, 301-311(2003).
  • S.K. Bouchillon, D.J. Hoban, J.L. Johnson, B.M. Johnson, D.L. Butler, K.A. Saunders, L.A. Miller, and J.A. Poupard, International Journal of Antimicrobial Agents, 23, 181-196 (2004).
  • P. Butaye, A. Cloeckaert and S. Schwarz, International Journal of Antimicrobial Agents, 22, 205-210 (2003).
  • U. Odakowska-Jedynak, L. Paczek, M. Krawczyk, K. Zieniewicz, P. Nckowski, J. Pawlak, W. Patkowski, A. Skwarek and A. Paczkowska, Transplantation Proceedings, 35, 2304-2306 (2003).
  • Yee Y.C., Clinical Microbiology Newsletter, 25, 9-16 (2003).
  • M.A. Abraham, P.P. Thomas, G.T. John, V. Job, Shankar V., Jacob C. K., Transplantation Proceedings, 35, 215-216 (2003).
  • E.M. Abdel-Moety, F.I. Khattab, K.M. Kelani and A.M. AbouAl-Alamein, Il Farmaco, 57, 931-938 (2003).
  • Bonhomme-Faivre L., Forestier F., Auchere D., Soursac M., Orbach- Arbouys S., Farinotti R., International Journal of Pharmaceutics, 238, 133-137 (2002).
  • D. Cordoba-Diaz, M. Cordoba-Diaz, S. Awad,and M. Cordoba-Borrego, International Journal of Pharma- ceutics, 226, 61-68 (2001).
  • J.R. Cupp-Vickery, C. Garcia, A. Hofacre, K. McGee-Estrada, Journal of Molecular Biology, 311, 101-110 (2001).
  • M.E. Carroll, U C. Campbell and P. Heideman, Experimental and Clinical Psychopharmacology, 9,
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Flavonol Glycosides from Asperula arvensis L.

Zühal GÜVENALP, L. Ömür DEMİREZER

Flavonal glycosides from Asperula arvensis L.

Zühal GÜVENALP, L.Ömür DEMİREZER

Synthesis and Characterization of New Triheterocyclic Compounds Consisting of 1,2,4-Triazol-3-one, 1,3,4-Thiadiazole and 1,3,4-Oxadiazole Rings

Neslihan DEMİRBAŞ

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

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

Synthesis and Structural Characterization of the 2-[(o-pyridyl)-sulfanylmethyl]-pyrimidine-silver(I) Complex [Ag2(opsp)2](NO3)2

Li-Rong WEN, Ming LI, Gui-Long ZNAO, Xue-Mei LI, Ou-Yang PINGKAI, Shu-Sheng ZHANG

Synthesis and structural characterization of the 2-[(o-pyridyl)-sulfanylmethyl]-pyrimidine-silver(I) complex $[Ag_2(opsp_2](NO_3)_2$

Ming LI, Li-Rong WEN, Gui-Long ZNAO, Ou-Yang PINGKAI, Shu-Sheng ZHANG, Xue-Mei LI

Synthesis and Antimicrobial Evaluation of Some New 2-(2-(p-chlorophenyl) benzimidazol-1-yl methyl)-5-substituted amino-[1,3,4]-thiadiazoles

Gülgün AYHAN KILCIGİL, Canan KUŞ

Anhydrous Proton Conductive Polystyrene Sulfonic Acid Membranes

Ayhan BOZKURT

Terpenoids and Steroids from the Roots of Salvia blepharochlaena

Ufuk KOLAK, Gülaçtı TOPÇU, Seher BİRTEKSÖZ

Synthesis and in vitro antimicrobial and cytotoxicity activities of 2-[(2-nitro-1-phenylalkyl) thio] benzoic acid derivaties

Taner KARAOĞLU, Berrin ÖZÇELİK, Semra UTKU, Ningur NOYANALPAN, Mehtap GÖKÇE, Erdoğan BERÇİN