Reactions of substituted furo[3,2-b]pyrrole-5-carboxhydrazides and their biological activity

• Authors: Renata Ga<parová , Daniel Zbojek , Margita Lácová , Katarína Král'ová , Anton Gatial , Branislav Horváth , Alžbeta Krutošíková
• Languages of publication: EN

Abstracts

EN

The reactions of substituted furo[3,2-b]pyrrole-5-carboxhydrazides 1 with 5-arylfuran-2-carboxaldehydes 2, 4,5-disubstituted furan-2-carboxaldehydes 3 and thiophene-2-carboxaldehyde 4 has been studied. The advantage of microwave irradiation on some of these reactions was reflected in the reduced reaction time and increased yields. Reactions of 1 with 4-substituted 1,3-oxazol-5(4H)-ones 11 led to diacylhydrazines 13 or to imidazole derivatives 14 depending on the temperature. 1,2,4-Triazole-3-thione 17 was synthesized by two-step reaction of 1 with phenylisothiocyanate and subsequent base-catalyzed cyclization of thiosemicarbazide 16. The effects of hydrazones 5–10 on inhibition of photosynthetic electron transport in spinach chloroplasts and chlorophyll content in the antialgal suspensions of Chlorella vulgaris were investigated.

Keywords

EN

furo[3,2-b]pyrrole-5-carboxhydrazide; furan-2-carboxaldehyde; thiophene-2-carboxaldehyde; antialgal activity; microwave irradiation

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2005
• Volume: 3
• Issue: 4
• Pages: 622-646

Dates

published

1 - 12 - 2005

online

1 - 12 - 2005

Contributors

author

Renata Ga<parová

• Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius, Námestie Jozefa Herdu 2, Sk-917 01, Trnava, Slovak Republic

author

Daniel Zbojek

• Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius, Námestie Jozefa Herdu 2, Sk-917 01, Trnava, Slovak Republic

author

Margita Lácová

• Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK 842 15, Bratislava, Slovak Republic

author

Katarína Král'ová

• Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK 842 15, Bratislava, Slovak Republic

author

Anton Gatial

author

Branislav Horváth

• Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, SK 842 15, Bratislava, Slovak Republic

author

Alžbeta Krutošíková

• Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius, Námestie Jozefa Herdu 2, Sk-917 01, Trnava, Slovak Republic

References

• [1] E. Jedlovská and E. Gavláková: “Synthesis of 2,3-Disubstituted 1,3,4-Oxadiazoles and their Precursors”, Collect. Czech. Chem. Commun. Vol. 59, (1994), pp. 1892–1896. http://dx.doi.org/10.1135/cccc19941892[Crossref]
• [2] E. Jedlovská and J. Leško: “A Simple One-pot Procedure for the Synthesis of 1,3,4-Oxadiazoles”, Synth. Commun., Vol. 24, (1994), pp. 1879–1885.
• [3] L.H. Cao and P.Y. Cui: “Synthesis of 2-Diyydrooxadiazolinyl Chromones”, J. Chinese Chem. Soc., Vol. 50, (2003), pp. 903–908.
• [4] A. Obreza and U. Urleb: “A new Synthesis of Substituted Benzaldehyde N-[(E)-Phenylmethylidene] hydrazones”, Acta Chim. Slov., Vol. 49, (2002), pp. 605–611.
• [5] H.M. El-Shaaer, P. Foltínová, M. Lácová, J. Chovancová and H. Stankovičová: “Synthesis, Antimycobacterial Activity and Bleaching Effect of Some Reaction Products of 4-Oxo-4H-benzopyran-3-carboxaldehydes with Aminobenzothiazoles and Hydrazides”, Il Farmaco, Vol. 53, (1998), pp. 224–232. http://dx.doi.org/10.1016/S0014-827X(98)00015-9[Crossref]
• [6] P. Foltínová, M. Lácová and D. Loos: “Activity of Some 3-Formylchromone Derivatives on the Chloroplast-free Mutant in Euglena gracillis”, Il Farmaco, Vol. 55, (2000), pp. 21–26. http://dx.doi.org/10.1016/S0014-827X(99)00114-7[Crossref]
• [7] M.M. Dutta, B.N. Goswami and J.C.S. Kataky: “Studies on Biologically Active Heterocycles. Part I. Synthesis and Antifungal Activity of Some New Aroyl Hydrazones and 2,5-Disubstituted-1,3,4-oxadiazoles”, J. Heterocycl. Chem., Vol. 23, (1986), pp. 793–795.
• [8] H.M. El-Shaaer, M. Lácová, Ž. Odlerová and M. Furdík: “Synthesis and Antimycobacterial effect of 3-Formylchromone N-Aroyl-orN-Alkylcarbonylhydrazones”, Chem. Papers, Vol. 48, (1994), pp. 344–347.
• [9] M.R.L. Santos, E.J. Barreiro, R. Braz-Filho and A.L.P. Miranda: “Synthesis of New Isochromanylacetylarylhydrazones Designed as Probable Non-Addictive Analgesic Agents”, J. Braz. Chem. Soc., Vol. 8, (1997), pp. 471–478. http://dx.doi.org/10.1590/S0103-50531997000500007[Crossref]
• [10] A. Krutošíková: “Bicyclic 5-5 Systems: Two Heteroatoms 1:1”, In: C.A. Ramsden (Ed.): Comprehensive Heterocyclic Chemistry II, Vol. 7, Pergamon, Oxford, 1996. pp. 1–47.
• [11] B.H. Lipshutz: “Five-membered heteroaromatic rings as intermediates in organic synthesis”, Chem. Rev., Vol. 86, (1986), pp. 795–819. http://dx.doi.org/10.1021/cr00075a005[Crossref]
• [12] X.L. Hou, H.Y. Cheung, T.Y. Hon, P.L. Kwan, T.H. Lo, S.Y. Tong and H.N.C. Wong: “Regioselective syntheses of substituted furans”, Tetrahedron, Vol. 54, (1998), pp. 1955–2020. http://dx.doi.org/10.1016/S0040-4020(97)10303-9[Crossref]
• [13] D.R. Shindhar, C.V.R. Sastry and N.K. Vaidya: “Synthesis and Antimicrobial Activity of Some New Arylsulfonylhydrazones Derived from 5-Substituted-2-furaldehydes and 3-(5-Nitro-2-furyl)acrolein”, J. Indian. Chem. Soc., Vol. 57, (1980), pp. 1118–1120; Chem. Abstr., Vol. 94, (1981), 174765j.
• [14] Y. Shigetaka, T. Akira, Y. Gang-Nan and H. Hsing-Chien: “Synthesis of 5-Nitrophenyl Furans and the Geometric Isomers of 5-(4-Nitrophenyl)-2-furylvinyl Benzenes”, Yakugaku Zasshi, Vol. 90, (1970), pp. 1150–1155; Chem. Abstr., Vol. 73, (1970), 120433x.
• [15] A. Krutošíková: “Synthesis and Reactions of Condensed Furan Derivatives”, Collect. Czech. Chem. Commun., Vol, 55, (1990), pp. 597–621. http://dx.doi.org/10.1135/cccc19900597[Crossref]
• [16] A. Krutošíková, C.A. Ramsden, M. Dandárová and A. Lyčka: “Synthesis and Reactions of Furo [2,3-b]pyrroles”, Molecules, Vol. 2, (1997), pp. 69–79.
• [17] A. Krutošíková, M. Dandárová and V. Bobošík: “Derivatives of Furo[3,2-b]pyrrole”, Collect. Czech. Chem. Commun., Vol. 59, (1994), pp. 473–481. http://dx.doi.org/10.1135/cccc19940473[Crossref]
• [18] M.K. Cyrański, T.M. Krygowski, A. Krutošíková and R. Sleziak: “Aromaticity of dihetero analogues of pentalene dianion. X-Ray and ab initio studies of eight methyl furo[3,2-b]pyrrole-5-carboxylate derivatives and five methyl furo[2,3-b]pyrrole-5-carboxylate derivatives”, Tetrahedron, Vol. 57, (2001), pp. 8867–8873. http://dx.doi.org/10.1016/S0040-4020(01)00854-7[Crossref]
• [19] R. Gašparová and M. Lácová: “Study of Microwave Irradiation Effect on Condensation of 6-R-3-Formylchromones with Active Methylene Compounds”, Collect. Czech. Chem. Commun., Vol. 60, (1995), pp. 1178–1185. http://dx.doi.org/10.1135/cccc19951178[Crossref]
• [20] M. Lácová, R. Gašparová, D. Loos, T. Liptay and N. Pronayová: “Effect of Microwave Irradiation on the Condensation of 6-Substituted 3-Formylchromones with Some Five-membered Heterocyclic Compounds”, Molecules, Vol. 5, (2000), pp. 167–178.
• [21] M. Lácová, H.M. El-Shaaer, D. Loos, M. Matulová, J. Chovancová and M. Furdík: “Evaluation of Effect of Microwave Irradiation on Syntheses and Reactions of Some New 3-Acyl-methylchromones”, Molecules, Vol. 3, (1998), pp. 120–131.
• [22] A. Loupy, A.Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault and D. Mathé: “New Solvent-Free Organic Synthesis Using Focused Microwaves”, Synthesis, (1998), pp. 1213–1234.
• [23] R. Frimm, J. Kováč and A. Krutošíková: “Furan derivatives XXXI α β-Unsaturated ketones of the phenylfuran series”, Chem. Zvesti, Vol. 27, (1973), pp. 101–106 and references cited.
• [24] D.A. Walker: “Preparation of Higher Plant Chloroplasts”, In: San Pietro (Ed.): Methods in Enzymology, Vol. 69, Part C. Academic Press, New York, 1980, pp. 94–104.
• [25] K. Král'ová, F. Šeršeň and M.J. Melník: “Inhibition of photosynthesis in Chlorela vulgaris by Cu(II) complexes with biologically active ligands”, Trace Microprobe Techniques, Vol. 16, (1998), pp. 491–500.
• [26] A.R. Wellburn: “The spectral determination of chlorophyll a and b, as well as total carotenoids, using various solvents with spectrophotometers of different resolution”, J. Plant. Physiol., Vol. 144, (1994), pp. 307–313. [Crossref]
• [27] Z. Puterová, H. Sterk and A. Krutošíková: “Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid”, Molecules, Vol. 9, (2004), pp. 11–21.
• [28] A.O. Fitton, J.R. Frost, H. Suschitzky and P.G. Houghton: “Conversion of 3-Formylchromones into Pyrrole and Thiophene Derivatives”, Synthesis, (1977), pp. 133–135.
• [29] M.M. Kidwai, N.H. Khan and M. Ali: “A Novel Synthesis of 3-Substituted Pyruvic Acids. A New Route to α,β-Diaminoacids”, Synth. Commun., Vol. 9, (1979), pp. 363–376.
• [30] C. Cativiela, M.D. de Villegas, J. Mayoral, A. Avenoza and M.A. Roy: “On the Synthesis of 3(5)-Carbomethoxy-4-hetarylpyrazoles”, J. Heterocycl. Chem., Vol. 25, (1988), pp. 851–855.
• [31] K. Nálepa and G. Zedníková: “Synthesis of Some 1,2,4-Trisubstituted 2-Imidazolin-5-ones”, Acta Univ. Palacki. Olomouc., Fac. Rerum Natur., Chemica, Vol. 38, (1999), pp. 53–57 and references cited.
• [32] C.H. Chu, X.P., Hui, Y. Zhang, Z.Y. Zhang, Z.C. Li and R.A. Liao: “Synthesis and antifungal Activities of ω-[4-Aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thio]-ω-(1H-1,2,4-triazol-1-yl) acetophenones”, J. Chinese Chem. Soc., Vol. 48, (2001), pp. 121–125.
• [33] A. Moreno-Manas, Y. Arredondo, R. Pleixats, M. Teixido, M.M. Haga, C. Palacin, J.M. Castello and J.A. Oritiz: “New Triazole Antifungal Agents Derived from Mercaptomethylisoxazoles”, J. Heterocycl. Chem., Vol. 29, (1992), pp. 1557–1560. http://dx.doi.org/10.1002/jhet.5570290631[Crossref]
• [34] F.E. Norrington, R.M. Hyde, S.G. Williams and R. Wootton: “Physicochemical-Activity Relations in Practice. 1. Rational and Self-Consistent Data Bank”, J. Med. Chem., Vol. 18, (1975), pp. 604–607. http://dx.doi.org/10.1021/jm00240a016[Crossref]
• [35] K. Král'ová, F. Šeršeň, L. Kubicová and K. Waisser: “Inhibitory Effect of Substituted Benzanilides on Photosynthetic Electron Transport in Spinach Chloroplasts”, Chem. Papers, Vol. 53, (1999), pp. 328–331.
• [36] M. Miletin, M. Doležal, V. Opletalová, J. Hartl, K. Král'ová and M. Macháček: “Some Anilides of 2-Alkylthio-and 2-Chloro-6-Alkylthio-4-Pyridinecarboxylic Acids: Synthesis and Photosynthesis-Inhibiting Activity”, Molecules, Vol. 6, (2001), pp. 603–613. http://dx.doi.org/10.3390/60700603[Crossref]
• [37] W. Draber, K. Tietjen, J.F. Kluth and A. Trebst: “Herbicides in Photosynthesis Research”, Angew. Chem. Int. Ed. Engl., Vol. 30, (1991), pp. 1621–1633. http://dx.doi.org/10.1002/anie.199116211[Crossref]
• [38] C. Fedtke: Biochemistry and Physiology of Herbicide Action, Springer Verlag Berlin, Heidelberg, New York, 1982, pp. 26–28 and 36–37.
• [39] L. Kubicová, M. Šustr, K. Král'ová, V. Chobot, J. Vytlačilová, L. Jahodár, P. Vuorela, M. Macháček and J. Kaustová: “Synthesis and Biological Evaluation of Quinazoline-4-thiones”, Molecules, Vol. 8, (2003), pp. 756–769.
• [40] R. Conrad, C. Buchel, C. Wilhelm, W. Arsalane, C. Berkaloff and J.C. Duval: “Changes in Yield of In-Vivo Fluorescence of Chlorophyll a as a Tool for Selective Herbicide Monitoring”, J. Appl. Phycol., Vol 5, (1993), pp. 505–516. http://dx.doi.org/10.1007/BF02182509[Crossref]

Identifiers

DOI

10.2478/BF02475192