Seven 2-furanthiocarboxyhydrazones were prepared, 5-nitro-furaldehyde-2-furanthiocarboxyhydrazone from the reaction of 2-furanthiocarboxyhydrazide with 5-nitro-2-furaldiacetate and the others from the condensation of 2-furanthiocarboxyhydrazide with aldehydes: 2- furaldehyde, benzaldehyde, p-hydroxybenzaldehyde, o-methoxybenzaldehyde, o-vanillin, and salicylaldehyde. The seven 2-furanthiocarboxyhydrazones were tested for their antibacterial activities against Staphyloccocus aureus and Bacillus subtilis. 5-Nitro-2-furaldehyde-2- furanthiocarboxyhydrazone was found to display the strongest bacterotoxicity

Chang, James C.

Li, Xiaorong

Sun, Zoumin

Name not available

Synthesis and Antibacterial Studies of Some 2-Furanthiocarboxyhydrazones

University of Northern Iowa

Journal of the Iowa Academy of Science: JIAS Volume 96 Number Article 9 1989 Synthesis and Antibacterial Studies of Some 2-Furanthiocarboxyhydrazones Xiaorong Li Shaanxi Teachers University Zoumin Sun Shaanxi Teachers University James C. Chang University of Northern Iowa Let us know how access to this document benefits you Copyright © Copyright 1989 by the Iowa Academy of Science, Inc. Follow this and additional works at: https://scholarworks.uni.edu/jias  Part of the Anthropology Commons, Life Sciences Commons, Physical Sciences and Mathematics Commons, and the Science and Mathematics Education Commons Recommended Citation Li, Xiaorong; Sun, Zoumin; and Chang, James C. (1989) "Synthesis and Antibacterial Studies of Some 2-Furanthiocarboxyhydrazones," Journal of the Iowa Academy of Science: JIAS, 96(2), 65-66. Available at: https://scholarworks.uni.edu/jias/vol96/iss2/9 This Research is brought to you for free and open access by the Iowa Academy of Science at UNI ScholarWorks. It has been accepted for inclusion in Journal of the Iowa Academy of Science: JIAS by an authorized editor of UNI ScholarWorks. For more information, please contact scholarworks@uni.edu. Jour. Iowa Acad. Sci. 96(2):65-66, 1989 Synthesis and Antibacterial Studies of Some 2-Furanthiocarboxyhydrazones XIAORONG 111, ZUOMIN SUN1 and JAMES C. CHANG2 1Department of Chemistry, Shaanxi Teachers University, Xian, Shaanxi, People's Republic of China 2Department of Chemistry, University of Northern Iowa, Cedar Falls, Iowa 50614 Seven 2-furanrhiocarboxyhydrazones were prepared, 5-nirro-furaldehyde-2-furanrhiocarboxyhydrazone from rhe reacrion of 2-furanrhio-carboxyhydrazide wirh 5-nirro-2-furaldiacerare and rhe orhers from the condensation of 2-furanrhiocarboxyhydrazide with aldehydes: 2-furaldehyde, benzaldehyde, p-hydroxybenzaldehyde, a-merhoxybenzaldehyde, a-vanillin, and salicylaldehyde. The seven 2-furanrhiocar-boxyhydrazones were rested for their anribacrerial activities against Staphyloccocm aurem and Bacillus s11btilis. 5-Nirro-2-furaldehyde-2-furanrhiocarboxyhydrazone was found ro display the strongest bacreroroxiciry. INDEX DESCRIPTORS: 2-Furanrhiocarboxyhydrazones, anribacrerial studies Thiosemicarbazones have been found to exhibit remarkable anti-tumor, 1 antiviral, 2 and antimalarial3 activities. Since thiosemicar-bazones and rhioacylhydrazones have similar structures, both having the - N - C = S group, it is reasonable to expect that the latter will also have bi6logical activities. The only work on 2-furanthiocarboxy-hydrazones reported in the literature are the syntheses of 2-furalde-hyde-2-furanthiocarboxyhydrazone, 4 p-aceramidobenzaldehyde-2-furanrhiocarboxyhydrazone, 4 and salicylaldehyde-2-furanthiocar-boxyhydrazone. 5 Now we report the synthesis of five new aldehyde-2-furanthiocarboxyhydrazones and a study of their antibacterial activi-ties. EXPERIMENTAL All chemicals used in this work were analytical reagent grade or of equivalent quality. 2-Furanthiocarboxyhydrazine and 2-furaldehyde-2-furanrhiocar-boxyhydrazone were prepared as described by Jensen and Pedersen. 4 Salicylaldehyde-2-furanthiocarboxyhydrazone was prepared by the method of Singh et al. 5 5-nirro-2-furaldiacerate was prepared by the method of Wang et al. 6 5-nitrofuraldehyde-2-furanrhiocarboxyhydrazone was prepared by condensing 5-nirro-2-furaldiacetate with 2-furanthiocarboxyhydra-zine in the presence of sulfuric acid. To 15 mL of 73% H1S04 was added 1.0 g of 5-nitro-2-furaldiacerare. The solution was heated to boiling for 5 minutes, and 0. 5 g of 2-furanrhiocarboxyhydrazine was added. The mixture was heated with stirring for an additional 20 minutes. The product appeared as yellow precipitate and was suction-filtered, washed with water and ethanol, and dried in vacuo. The yield was 97%. It is insoluble in water, soluble in acetone, and slightly soluble in methanol and ethanol. All other 2-furanthiocarboxyhydrazones were prepared by condens-ing the appropriate aldehyde with 2-furanrhiocarboxyhydrazine in ethanol. In a typical preparation, 0.68 g (5 mmol) of o-merhoxyben-zaldehyde and 0. 7 1 g (5 mmol) of 2-furanthiocarboxyhydrazine were added to 5mL of ethanol. The mixture was stirred at 50°C for 1 hour and left overnight at room temperature. Then water was added dropwise to the ethanol mixture to precipitate the yellow prod~ct. The product was filtered, washed with ethanol, and recrystallized from 50% ethanol. The yields are given in Table 1. These compounds are all soluble in methanol and ethanol. Carbon, hydrogen, and nitrogen were determined by microanal-yses. IR spectra were measured, as KBr pellets, by a Perkin-Elmer Model 983 spectrophotometer. UV spectra were measured by a UV-260 spectrophotometer, using ethanol as the solvent. The antibacterial activities of the 2-furanthiocarboxyhydrazones were evaluated against Staphyloccocus aureus and Bacillus subtilis by the agar plate technique,7 using fine suspensions of the compounds in water at concentrations of 128, 64, 32, 16, 8, 4, 2, and 1 µg mL - 1• The culture medium was MPA, and furalcilinum was used as a control. After incubation at 32 ± 1°C for 24 hours, the plates were examined and the minimum inhibitory concentration (MIC) of each compound was recorded. Each assay was done in triplicate. RESULTS AND DISCUSSION The formation of the 2-furanrhiocarboxyhydrazones followed the reactions below: ~,-01 ~-01 and R-CHO + H2NNH-C -- R-CH•NNH-C (11 to Vll), 0 0 where R = 2-furyl (II), p-hydroxyphenyl (III), o-methoxyphenyl (IV), phenyl (V), 2-hydroxy-3-methoxyphenyl (VI), and o-hydroxyphenyl (VII). The analytical results, melting points, and the percentage yields of the five new 2-furanthiocarboxyhydrazones are given in Table 1. All the compounds exhibit IR bands at 3136-3278 cm - 1, 1599-1620 cm - 1, and 600-710 cm - 1, attributed to the N-H, 8 C = N, 9 and C = S 10 vibrations, respectively. All the compounds prepared showed a maximum near 320 nm in their UV spectra. This may be attributed to the 1T-1T* transition originated from the - C = S group. 5 The similarities in the IR and UV spectra of these compounds indicated that they all have similar structure. In Table 2 are listed the minimum inhibitory concentrations of the seven compounds studied, as compared to the control, furalcilinum (VIII). Ir can be seen that 5-nitro-2-furaldehyde-2-furanthiocarboxy-hydrazone has strong inhibitory ability to the rwo bacteria rested. Among the substituted benzaldehyde-2-furanthiocarboxyhydra-zones, the inhibitory abilities decreases in the following sequence, in terms of the substituents: o-merhoxy =unsubstituted > a-hydroxy > 2-hydroxy-3-merhoxy > p-hydroxy. This sequence shows that a hydroxy group on the benzene ring decreases the antibacterial activity. This may be explained by the reduced polarity of the compound without the hydroxy group, increasing the hydrophobic character of the compounds. The in-creased hydrophobic nature will favor the permeation of the com-66 JOUR. IOWA ACAD. SCI. 96(1989) Table 1. Analytical Results of New 2-Furanthiocarboxyhydrazones Analyses, Found (Calcd.) No. R c I 5-nitro-2-furyl 45.00(45.28) III p-hydroxyphenyl 58.80(58. 52) IV o-methoxyphenyl 60. 50(59.98) v phenyl 63.04(62. 59) VI 2-hydroxy-3-methoxyphenyl 56.76(56.51) pounds through the lipoid layer of the bacteria membrane. 11 Cu(II), Ni(II), and Zn(II) complexes of some of the 2-furanthiocar-boxyhydrazones have been prepared and tested against several organ-isms. 12 It was found that, for example, Cu(II) complexes of o-methoxybenzaldehyde-2-furanthiocarboxyhydrazone and 5-nitro-2-furaldehyde-2-furanthiocarboxyhydrazone exhibit strong antibacter-ial activity. The 2-furanthiocarboxyhydrazones and their transition-metal complexes may also be antifungal, and further work in this respect is in progress. Table 2. Minimum Inhibitory Concentration (µg mL - 1) of the 2-Furanthiocarboxyhydrazones No. R S. aureus B. subtilis I 5-nitro-2-furyl II 2-furyl III p-hydroxyphenyl IV o-methoxyphenyl V phenyl VI 2-hydroxy-3-methoxyphenyl VII o-hydroxyphenyl Furalcilinum •NI= no inhibition. 16 NI" NI 32 32 NI 128 16 4 32 NI 32 32 128 64 4 H 2.66(2.66) 4. 15(4.09) 4.73(4.65) 4.35(4.38) 4. 34(4. 38) N 15.49(15.84) 11. 26(11.3 7) 10.89(10.76) 13.10(12.16) 10.03(10.14) m.p., °C 157-158 174-175 142-143 99-100 164-165 REFERENCES Percentage Yield 97% 96% 95% 74% 98% 1 BROCKMAN, R.W., THOMSON,J.R., BELL, M.J., SKIPPER, H.E. 1956. Cancer Res., 16, 167. 2 MINTON, S.A., OFFICER, J.E., THOMPSON, R.L. 1953.). lm-munol., 70, 222. 3 KLAYMAN, D.L., BARTOSEVICH, J.E., GRIFFIN, T.S., MASON, C.J., SCOVILL, J.P. 1979.). Med. Chem .. 22, 855. 4 JENSEN, K.A., PEDERSEN, C. 1961. Acta Chem. Scand .. 15. 1097. 5 SINGH, N.K., AGRAWAL, S., AGGARWAL, R.C. 1985. Synth. React. Inorg. Met.-Org. Chem. 15, 75. 6 WANG, H., SONG, S., SONG, D., YANG, Z. 1986. Linehan H11ax11e Yu Gongye, 6(2), 29. 7 DAI, Z. 1985. "Clinical Antimicrobial Materia Medica," People's Health Press, Beijing, PRC, p. 9. 8 NAKANISHI, K., SOLOMON, P.H. 1977. "Infrared Absorption Spec-troscopy," 2nd ed., Holden-Day, San Francisco, p. 33. 9 KOVACIC, J.E. 1967. Spectrochim. Acta, 23A, 183. 10 DESSEYN, H.O., AARTS, A.J., HERMAN, M.A. 1980. Spectrochim. Acta, 36A, 59. 11 SINGH, H., YADAV, L.D.S., MISHRA, S.B.S. 1981.). lnorf!.. Nucl. Chem., 43, 1701. 12 11, X., SUN, Z., CHANG, J.C. 1988. Synth. React. Inorf!.. Met.-Orf!.. Chem., 18, 657. 

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Synthesis and Antibacterial Studies of Some 2-Furanthiocarboxyhydrazones

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