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Symmetrical Acyclic Aryl Aldazines with Antibacterial and Antifungal Activity

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DOI: 10.4236/pp.2011.21001    5,681 Downloads   13,618 Views   Citations

ABSTRACT

A series of 22 symmetrical acyclic aromatic aldazines were obtained and their qualitative antimicrobial activities were evaluated against 10 bacterial and 3 fungal species. The results demonstrated that the bi- and polycyclic aromatics studied are remarkably more active than benzaldazines. The latter possess antibacterial activities only, which were dramatically reduced by the introduction of substituents. The tests showed that the activities are strongly dependent on the type and position of the substituents and that the effects on antibacterial and antifungal activities are the opposite. 2-Naphtaldazine was significantly more active than its position isomer 1-naphthaldazine against Saccharomyces cerevisiae and Penicillium chrysogenum, whereas both compounds possess commensurable activities towards Candida tropicalis and the bacterial strains. From the other side, the presence of 4-hydroxy substituent in 1-naphthaldazine reduced the antibacterial and increased the antifungal activities, while the influence of 2-hydroxy group led to reversed results.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

V. Kurteva, S. Simeonov and M. Stoilova-Disheva, "Symmetrical Acyclic Aryl Aldazines with Antibacterial and Antifungal Activity," Pharmacology & Pharmacy, Vol. 2 No. 1, 2011, pp. 1-9. doi: 10.4236/pp.2011.21001.

References

[1] D. Kolbah and D. Koruncev, “Methoden zur Herstellung und Umwandlung von Azinen,” In: Methoden der Organischen Chemie (Houben-Weyl), Vol. 10, part 2, Georg Thieme Verlag, Stuttgart, 1967, pp. 85-122.
[2] S. Dayagi and Y. Degani, “Formation of the Car-bon-Nitrogen Double Bond,” In: S. Patai, Ed., The Chemistry of the Carbon-Nitrogen Double Bonds, Inter-science, New York, 1970, pp. 61-147. doi:10.1002/9780470771204.ch2
[3] W. Borsche, “Eine neue Reaction der Semicarbazone,” Berichte der Deutschen Chemischen Gesellschaft, Vol. 34, No. 3, October-December 1901, pp. 4297-4302. doi: 10.1002/cber. 190103403161
[4] S. N. Shah and N. K. Chudgar, “Thermolysis of Semi-carbazones to the Corresponding Azines Through Reactive N-Substituted Isocyanate Intermediates,” Molecules, Vol. 5, No. 4, April 2000, pp. 657-664. doi:10.3390/50400657
[5] H. Loghmani-Khouzani, M. M. M. Sadeghi, J. Safari and M. S. Abdorrezaie, “A Convenient Synthesis of Azines under Solvent-Free Conditions Using Microwave Irradiation,” Journal of Chemical Research (S), No. 2, February 2001, pp. 80-81.
[6] S. P. Simeonov, V. B. Kurteva and R. P. Bontchev, “One-Pot Solvent-Free Synthesis of Symmetrical Azines under Microwave Irradiation,” Bulgarian Chemical Communications, Vol. 40, No. 4, 2008, pp. 409-417.
[7] W. J. Haggerty and C. C. Cheng, “Antitumor Activity of Some Azine and Hydrazone Derivatives of 1,4-Dimeth- oxy-2-Butanone,” Journal of Medicinal Chemistry, Vol. 13, No. 3, May 1970, pp. 574-575. doi:10.1021/jm00297a067
[8] J. R. Dimmock, P. Kumar, J. W. Quail, U. Pugazhenthi, J. Yang, M. Chen, R. S. Reid, T. M. Allen, G. Y. Kao, S. P. C. Cole, G. Batist, J. Balzarini and E. De Clercq, “Synthesis and Cytotoxic Evaluation of Some Styryl Ketones and Related Compounds,” European Journal of Medicinal Chemistry, Vol. 30, No. 3, 1995, pp. 209-217.
[9] A. I. Khodair and P. Bertrand, “A New Approach to the Synthesis of Substituted 4-Imidazolidinones as Potential Antiviral and Antitumor Agents,” Tetrahedron, Vol. 54, No. 19, May 1998, pp. 4859-4872. doi:10.1016/S0040-4020(98)00170-7
[10] H. I. Gul, M. Gul, J. Veps?lainen, E. Erciyas and O. H?nninen, “Cytotoxicity of Some Azines of Acetophenone Derived Mono-Mannich Bases against Jurkat Cells,” Biological and Pharmaceutical Bulletin, Vol. 26, No. 5, May 2003, pp. 631-637. doi:10.1248/bpb.26.631
[11] H. N. Pati, U. Das, R. K. Sharma and J. R. Dimmock, “Cytotoxic Thiol Alkylators,” Mini Reviews in Medicinal Chemistry, Vol. 7, No. 2, February 2007, pp. 131-139. doi:10.2174/138955707779802642
[12] N. Haider, T. Kabicher, J. K?ferb?ck and A. Plenk, “Synthesis and In-vitro Antitumor Activity of 1-[3- (Indol-1-yl) prop-1-yn-1-yl] phthalazines and Related Compounds,” Molecules, Vol. 12, No. 8, August 2007, pp. 1900-1909. doi:10.3390/12081900
[13] Y. Sawa and M. Hoten, “Antibacterial Activity of Basic Dyes on the Dyed Acrylic Fibers,” Sen’i Gakkaishi, Vol. 57, No. 5, May 2001, pp. 153-158. doi:10.2115/fiber.57.153
[14] R. N. Asolkar, V. P. Kamat, I. Wagner-D?bler and H. Laatsch, “Limnazine, the First Bacterial Azine Derivative from Bacillus sp. GW90a,” Journal of Natural Products, Vol. 65, No. 11, Novembre 2002, pp. 1664-1666. doi: 10.1021/np020108n
[15] I. A. Danish and K. R. Prasad, “Synthesis and Charac- terisation of N,N’-Biscarbazolyl Azine and N,N’-Carba-zolyl Hydrazine Derivatives and Their Antimicrobial Studies,” Acta Pharmaceutica, Vol. 54, No. 2, June 2004, pp. 133-142.
[16] H. I. Gul, F. Sahin, M. Gul, S. Ozturk and K. O. Yerdelen, “Evaluation of Antimicrobial Activities of Several Mannich Bases and Their Derivatives,” Archiv der Pharmazie, Vol. 338, No. 7, July 2005, pp. 335-338. doi:10.1002/ardp.200400962
[17] M. N. Kumaraswamy and V. P. Vaidya, “Novel Method for the Synthesis of Symmetrical and Asymmetrical Azines Involving Naphtho [2,1-b] Furan and Their Antimicrobial Activity,” Indian Journal of Heterocyclic Chem- istry, vol. 14, no. 3, January-March 2005, pp. 193-196.
[18] J. Jayabharathi, A. Thangamani, M. Padmavathy and B. Krishnakumar, “Synthesis and Microbial Evaluation of Novel N(1)-Arilidene-N(2)-t(3)-methyl-r(2), c(6)-diaryl- piperidin-4-one Azine Derivatives,” Medicinal Chemistry Research, Vol. 15, No. 7-8, August 2007, pp. 431-442. doi: 10.1007/ s00044-006-0014-0
[19] J. Jayabharathi, V. Thanikachalam, A. Thangamani and M. Padmavathy, “Synthesis, AM1 Calculation, and Bio- logical Studies of Thiopyran-4-one and Their Azine Derivatives,” Medicinal Chemistry Research, Vol. 16, No. 6, December 2007, pp. 266-279. doi:10.1007/s00044-007-9029-4
[20] G. Aridoss, S. Amirthaganesan, M. S. Kim, J. T. Kim and Y. T. Jeong, “Synthesis, Spectral and Biological Evaluation of Some New Thiazolidinones and Thiazoles Based on t-3-Alkyl-r-2,c-6-diarylpiperidin-4-ones,” European Journal of Medicinal Chemistry, Vol. 44, No. 10, October 2009, pp. 4199-4210. doi:10.1016/j.ejmech. 2009.05.015
[21] R. W. Lange, “BXT-51072 OXIS International,” Current Opinion in Anti-inflammatory and Immunomodulatory Investigational Drugs, Vol. 2, No. 4, 2000, pp. 338-341.
[22] J. L. Vennerstrom, M. T. Makler, C. K. Angerhofer and J. A. Williams, “Antimalarial Dyes Revisited-Xanthenes, Azines, Oxazines, and Thiazines,” Antimicrobial Agents and Chemotherapy, vol. 39, no. 12, December 1995, pp. 2671-2677.
[23] F. D. Popp, “Potential Anticonvulsants .8. Some Hydrazones of Indole-3-Carboxaldehyde,” Journal of Hetero-cyclic Chemistry, Vol. 21, No. 2, 1984, pp. 617-619. doi:10.1002/jhet.5570210273
[24] H. I. Gul, U. Calis and J. Vepsalainen, “Synthesis of Some Mono-Mannich Bases and Corresponding Azine Derivatives and Evaluation of Their Anticonvulsant Activity,” Arzneimittel-Forschung-Drug Research, Vol. 54, No. 7, 2004, pp. 359-364.
[25] M. Eberle, S. Farooq, A. Jeanguenat, D. Mousset, A. Steiger, S. Trah, W. Zambach and A. Rindlisbacher, “Azine Derivatives as a New Generation of Insect Growth Regulators,” Chimia, Vol. 57, No. 11, 2003, pp. 705-709.
[26] I. Picón-Ferrer, F. Hueso-Ure?a, N. A. Illán-Cabeza, S. B. Jiménez-Pulido, J. M. Martínez-Martos, M. J. Ramírez- Expósito and M. N. Moreno-Carretero, “Chloro-fac-tricarbonylrhenium(I) Complexes of Asymmetric Azines Derived from 6-Acetyl-1,3,7-trimethylpteridine-2,4(1h,3h)-dione with Hydrazine and Aromatic Aldehydes: Preparation, Structural Characterization and Biological Activity Against Several Human Tumor Cell Lines,” Journal of Inorganic Biochemistry, Vol. 103, No. 1, January 2009, pp. 94-100.
[27] M. Revanasiddappa, T. Suresh, S. Khasim, S. C. Raghavendray, C. Basavaraja and S. D. Angadi, “Electrical Conductivity Studies on Co(II), Cu(II), Ni(II) and Cd(II) Complexes of Azines,” E-Journal of Chemistry, Vol. 5, No. 4, 2008, pp. 395-403.
[28] G. Gürk?k, N. Altanlar and S. Suzen, “Investigation of Antimicrobial Activities of Indole-3-Aldehyde Hy- drazide/Hydrazone Derivatives,” Chemotherapy, Vol. 55, No. 1, 2009, pp. 15-19.
[29] G. Gürk?k, T. Coban and S. Suzen, “Melatonin Analogue New Indole Hydrazide/Hydrazone Derivatives with An- tioxidant Behavior: Synthesis and Structure–Activity Relationships,” Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 24, No. 2, April 2009, pp. 506-515.
[30] J. R. Dimmock, K. K. Sidhu, S. D. Tumber, S. K. Basran, M. Chen, J. W. Quail, J. Yang, I. Rozas and D. F. Weaver, “Some Aryl Semicarbazones Possessing Anticonvulsant Activitie,” European Journal of Medicinal Chemistry, Vol. 30, No. 4, 1995, pp. 287-301.
[31] J. A. O’Brien, W. Lemaire, T.-B. Chen, R. S. L. Chang, M. A. Jacobson, S. N. Ha, C. W. Lindsley, H. J. Schaffhauser, C. Sur, D. J. Pettibone, P. J. Conn and D. L. Williams Jr, “A Family of Highly Selective Allosteric Modulators of the Metabotropic Glutamate Receptor Subtype 5,” Molecular Pharmacology, Vol. 64, No. 3, September 2003, pp. 731-740.
[32] L. Horner, W. Kirmse and H. Fernekess, “Azinmonoxyde, Darstellung und Eigenschaften,” Chemische Berichte, Vol. 94, No. 1, Januar 1961, pp. 279-290.
[33] D. Vorl?nder, “Ueber krystallinisch-flüssige Substanzen,” Berichte der deutschen chemischen Gesellschaft, Vol. 39, No. 1, Januar-Februar 1906, pp. 803-810.
[34] H. Franzen and T. Eichler, “Zur Kenntnis der Benzalhydrazine,” Journal für Praktische Chemie, Vol. 82, No. 1, December 1910, pp. 241-251.
[35] A. P. Terent’ev, E. G. Rukhadze, G. P. Talyzenkova and G. V. Panova, “Azomethines of o-vanilin and their chelate compounds,” Zhurnal Obshchei Khimii, Vol. 36, No. 9, 1966, pp. 1590-1594.
[36] G. F. D’alelio, J. V. Crivello, R. K. Schoenig and T. F. Huemmer, “Polymeric Schiff Bases. II: The Synthesis of Azomethines by a Continuous Azeotropic Method,” Journal of Macromolecular Science, Part A Pure and Applied Chemistry, Vol. 1, No. 7, 1967, pp. 1251-1258.
[37] T. Curtius, F. Mayer, R. Korte and H. Wewer, “über die Reduktion der aromatischen Aldazine,” Journal für Praktische Chemie, vol. 85, no. 1, Mai 1912, pp. 137-188.
[38] T. Curtius and H. Pauli, “Oxydation von symmetrischen secund?ren Benzylhydrazinen, R.CH2.NH.NH.CH2.R, zu Hydrazonen, R.CH:N.NH.CH2.R,” Berichte der deutschen chemischen Gesellschaft, Vol. 34, No.1, Januar-April 1901, pp. 847-853.
[39] G. Lock and K. Stach, “über die katalytische Zersetzung der Hydrazone, I. Mitteil.: Aromatische Aldehydhydra-zone,” Berichte der deutschen chemischen Gesellschaft, Vol. 76, No. 12, Dezember 1943, pp. 1252-1256.
[40] N. P. Buu-Ho? and G. Saint-Ruf, “Synthèse des diaryl-1,2 éthylènes par thermolyse des aldazines en milieu liquide,” Bulletin de la Société Chimique de France, No. 6, 1968, pp. 2489-2492.
[41] N. P. Buu-Ho? and G. Saint-Ruf, “La Thermodécomposition des Aldazines Aromatiques et ses Applications à la Chimie Préparative,” Bulletin de la Société Chimique de France, No. 3, 1967, pp. 955-960.
[42] T. Curtius, R. Glaser, G. Detoros, L. F. Potter, K. Traumann, L. F. Guttmann, J. Schmittmann and H. Pauli, “über die Reduktion der aromatischen Aldazine. Reduktion von o- und m-Oxybenzaldazin in alkalischer L?sung,” Journal für Praktische Chemie, Vol. 85, No. 1, Mai 1912, pp. 393-484.
[43] L. Gattermann, “Synthesen Aromatischer Aldehyde,” Justus Liebigs Annalen der Chemie, Vol. 357, No. 2-3, 1907, pp. 313-383.
[44] L. Gattermann and T. von Horlacher, “Synthese von Oxyaldehyden der Naphtalinreihe,” Berichte der deutschen chemischen Gesellschaft, Vol. 32, No. 1, Januar-April 1899, pp. 284-286.
[45] G. W. Monier-Williams, “Synthesis of Aldehydes by Grignard’s Reaction,” Journal of the Chemical Society, Vol. 89, No. 1, 1906, pp. 273-280.
[46] L. Y. Malkes and A. I. Timchenko, “Synthesis of trans-n, n’-diphenylstilbene,” Zhurnal Obshchei Khimii, Vol. 31, No. 2, 1961, pp. 560-562.
[47] G. Saint-Ruf, B. Kirkiacharian, N. P. Buu-Ho? and C. Mentzer, “Détection de la Formation de Radicaux Libres au Cours de la Thermolyse des Aldazines Aromatiques,” Bulletin de la Société Chimique de France, No. 8, 1967, pp. 3078-3079.
[48] European Pharmacopoia, 3th Edition, Deutscher Apotheker Verlag, Stuttgart, 1997, pp. 113-118.

  
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