Synthesis and in vitro antibacterial evaluation of some thiosemicarbazides and thiosemicarbazones

Abstract

In the present study various thiosemicarbazides and thiosemicarbazones were synthesized and screened for their antimicrobial activity. Among the ligands tested, compounds 1, 3, 4 and 5 demonstrated inhibitory effects at 0.4 - 0.5 μM concentrations against E. coli while 1-(4-fluorobenzoyl)-N4-ethyl-thiosemicar-bazide (3) demonstrated the maximum inhibitory effective compound against E. coli, also possessing high water solubility. Instead, compound 3 demonstrated weak antibiotic effects against S. aurous while compounds 4 - 6 demonstrated significant antibacterial effects at 0.4 - 0.42 μM against the latter organism. Chloramphenicol was used as the positive control.

Share and Cite:

Sheikhy, M. , Jalilian, A. , Novinrooz, A. and Motamedi-Sedeh, F. (2012) Synthesis and in vitro antibacterial evaluation of some thiosemicarbazides and thiosemicarbazones. Journal of Biomedical Science and Engineering, 5, 39-42. doi: 10.4236/jbise.2012.52006.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] Barchiesi, F., Arzeni, D., Fothergill, A.W., Di Francesco, L.F., Caselli, F., Rinaldi, M.G. and Scalise, G. (1999) In vitro activities of the new antifungal triazole SCH 56592 against common and emerging yeast pathogens. Antimicrob Agents Chemother, 44, 226-229. doi:10.1128/AAC.44.1.226-229.2000
[2] Shafiee, A., Jalilian, A.R. and Tabatabaiee-Yazdi, M. (1998) Synthesses, antibacterial and antifungal activities of substituted-thiazolo-1,3,4-thiadiazoles, oxadiazoles and 1, 2,4-triazoles. Iranian Journal of Chemistry & Chemical Engineering, 17, 14-20.
[3] Jalilian, A.R., Sattari, S., Bineshmarvasti, M., Shafiee, A. and Daneshtalab M. (2000) Synthesis and in vitro antifungal and cytotoxicity evaluation of thiazolo-4H-1,2,4-triazoles and 1,2,3-thiadiazolo-4H-1,2,4-triazoles. Arch Pharm (Weinheim), 333, 347-354. doi:10.1002/1521-4184(200010)333:10<347::AID-ARDP347>3.0.CO;2-6
[4] Jalilian, A.R., Sattari, S., Bineshmarvasti, M. and Daneshtalab, M. (2003) A shafiee, synthesis and in vitro antifungal and cytotoxicity evaluation of substituted 4,5-dihydronaphtho[1,2-d][1,2,3]thia(or selena)diazoles. Il Farmaco, 58, 63-68.
[5] Shafiee, A.R. and Jalilian, B. (2000) Rezaei, selenium heterocycles XLIV. Syntheses of 8,9-dihydro-1,2,3-thiadiazolo[4,5-a]-4,7-dihydronaphthalene and 1,2,3-selena- diazolo[4,5-a]-4,7-dimethoxynaphthalene. Journal of Heterocyclic Chemistry, 37, 1325-1327. doi:10.1002/jhet.5570370551
[6] Varvaresou, T., Siatra-Papastaikoudi, A., Tsotinis, D., Tsantili-Kakoulidou, A. and Amvakides, V.A. (1998) Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2, 4-triazole. Farmaco, 53, 320-326.
[7] Bineshmarvasti, M., Sharifzadeh, M., Jalilian, A.R., Soltaninejad, K. and Shafiee, A. (2003) Syntheses and anticonvulsant activity of N4-substituted triazolylthiazoles. Daru, 11, 74-78.
[8] Boon, W.R. (1945) The action of thionyl chloride on 2: 4-dimethylthiazole-5-carboxylic acid. Journal of the Chemical Society, 162, 601-603. doi:10.1039/jr9450000601
[9] Kane, J.M., Staeger, M.A., Dalton, C.R., Miller, F.P., Dudley, M.W., Ogden, A.M., Kehne, J.H., Ketteler, H.J., McCloskey, T.C. and Senyah, Y. (1994) 5-Aryl-3-(alkylthio)-4H-1,2,4-triazoles as selective antagonists of stry-chnine-induced convulsions and potential antispastic agents. Journal of Medicinal Chemistry, 37, 125-132. doi:10.1021/jm00027a015
[10] Gingras, B.A., Suprunchuk, T. and Bayley, C.H. (1962) The preparation of some thiosemicarbazones and their copper complexes, Part III. Canadian Journal of Chemistry, 40, 1053-1057. doi:10.1139/v62-161
[11] Muanza, D.N., Kim, B.W., Eluer, K.L. and Williams, L. (1994) Antibacterial and antifungal activities of nine medicinal plants of Zaire. International Journal of Pharmacology, 32, 337-345.
[12] Mitscher, L., Lue, R., Bathala, M.S., Wu, W. and Beal, J.L. (1972) Antimicrobial agents from higher plants. I. Introduction, rational and methodology. Lloydia, 35, 157-161.
[13] National Committee for Clinical Laboratory Standards (1992) Reference method for broth dilution antifungal susceptibility testing for yeasts. Proposed Standards, Document M27-P, Villanova.

Copyright © 2021 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.