Abstract
A series of mono and bis 2-2-(arylidineaminophenyl)indole azomethines have been synthesized by a condensation reaction of 2-(2-amino phenyl) indole with various mono and diketones R-CO-Rl /R-CO-X-CO-Rl (1:1/2:1 ratio) in ethanol media. The synthesized azomethines were characterized via IR, 1H-NMR, 13C-NMR, MS and elemental analysis. The antimicrobial activity of these compounds against different bacteria and fungi was also evaluated.
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Amudha, P., Akilan, P., and Kandaswamy, M., Synthesis, spectral, electrochemical and magnetic properties of new symmetrical and unsymmetrical dinuclear copper(II) complexes derived from binucleating ligands with phenol and benzimidazole donors. Polyhedron, 18, 1355–1362 (1999).
Andreani, A. and Maselli, S., Anti-inflammatory activity of N-benzoyl-isatinic acids and N-p-chlorobenzoyl isatinic acids. Boll. Chim. Farm., 116, 493–495 (1977).
Billimoria, A. D. and Cava, M. P., Chemistry of indolo[)1,2-c])quinazoline: an approach to the marine alkaloid hinckdentine A. J. Org. Chem., 59, 6777–6782 (1994).
Clavel, M., Bonneterre, J., d’Allens, H., and Paillarse, J. M., Oral ondansetron in the prevention of chemotherapyinduced emesis in breast cancer patients. Eur. J. Cancer, 31A, 15–19 (1995).
Gitto, R., De Luca, L., Ferro, S., Citraro, R., De Sarro, G., Costa, L., Ciranna, L., and Chimirri, A., Development of 3-substituted-1H-indole derivatives as NR2B/NMDA receptor antagonists. Bioorg. Med. Chem., 17, 1640–1647 (2009).
Gurkok, G., Altanlar, N., and Suzen, S., Investigation of antimicrobial activities of indole-3-aldehyde hydrazide/hydrazone derivatives. Chemotherapy, 55, 15–19 (2009).
Habib, N. S., Soliman, R., El-Tombary, A. A., El-Hawash, S. A., and Shaaban, O. G., Synthesis of thiazolo[)4,5-d])pyrimidine derivatives as potential antimicrobial agents. Arch. Pharm. Res., 30, 1511–1520 (2007).
Hurdle, J. G., O’Neill, A. J., and Chopra, I., Anti-staphylococcal activity of indolmycin, a potential topical agent for control of staphylococcal infections. J. Antimicrob. Chemother., 54, 549–552 (2004).
Jung, H. J., Singh, N., and Jang, D. O., Highly Fe3+ selective ratiometric fluorescent probe based on imine-linked benzimidazole. Tetrahedron Lett., 49, 2960–2964 (2008).
Jung, J. K., Jung E. K., Nam-Goong, K., Cho, J. S., Kim, H. M., Park, S. G., Yoo, Y. A., Kwon, J. H., and Lee, H. S., Synthesis and cytotoxic activities of 8-alkyl or 8-aryl-8,9-dihydro-7H-isoindolo[5,6-g]quinoxaline-7,9-diones. Arch. Pharm. Res., 29, 276–281 (2006).
Kaplancikli, Z. A., Turan-Zitouni, G., Revial, G., and Guven, K., Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl) sulfanyl]acetylamino]thiazoles. Arch. Pharm. Res., 27, 1081–1085 (2004).
Kiang, A. K., Mann, F. G., Prior, A. F., and Topham, A., The action of acyl cyanides on 2-and 1:2-substituted indoles. Part II. Derivatives of 2-o-aminophenylindole. J. Chem. Soc., 1319–1331 (1956).
Krönig, B., Pittrow, D. B., Kirch, W., Welzel, D., and Weidinger, G., Different concepts in first-line treatment of essential hypertension. Comparison of a low-dose reserpine-thiazide combination with nitrendipine monotherapy. Hypertension, 29, 651–658 (1997).
Küçükgüzel, I., Güniz Küçükgüzel, Ş., Rollas, S., Ötük-Sani, G., Özdemir, O., Bayrak, I., Altu, T., and Stables, J. P., Synthesis of some 3-(arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1,2,4-triazole derivatives and their anticonvulsant activity. Farmaco, 59, 893–901 (2004).
Mallié, M., Bastide, J. M., Blancard, A., Bonnin, A., Bretagne, S., Cambon, M., Chandenier, J., Chauveau, V., Couprie, B., Datry, A., Feuilhade, M., Grillot, R., Guiguen, C., Lavarde, V., Letscher, V., Linas, M. D., Michel, A., Morin, O., Paugam, A., Piens, M. A., Raberin, H., Tissot, E., Toubas, D., and Wade, A., In vitro susceptibility testing of candida and aspergillus spp. to voriconazole and other antifungal agents using Etest: results of a french multicentre study. Int. J. Antimicrob. Agents, 25, 321–328 (2005).
Mihelic, R., Kaufman, J., Lonial, S., and Flowers, C., Maintenance therapy in lymphoma. Clin. Lymphoma Myeloma, 7, 507–513 (2007).
Mostafa, Y. A. H., Hussein, M. A., Radwan, A. A., and Kfafy, A. E. H. N., Synthesis and antimicrobial activity of certain new 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Arch. Pharm. Res., 31, 279–293 (2008).
Pignatello, R., Panico, A., Mazzone, P., Pinizzotto, M. R., Garozzo, A., and Fumeri, P. M., Schiff bases of N-hydroxy-N′-aminoguanidines as antiviral, antibacterial and anticancer agents. Eur. J. Med. Chem., 29, 781–785 (1994).
Popp, F. D., Parson, R., and Donigan, B. E., Potential anticonvulsants. III. the condensation of isatin with cyclic ketones. J. Heterocycl. Chem., 17, 1329–1330 (1980).
Reddy, P. M., Ho, Y. P., Shanker, K., Rohini, R., and Ravinder, V., Physicochemical and biological characterization of novel macrocycles derived from o-phthalaldehyde. Eur. J. Med. Chem., 44, 2621–2625 (2009).
Rohini, R., Reddy, P. M., Shanker, K., and Ravinder, V., New mono, bis-2,2-(arylidineaminophenyl)benzimidazoles: synthesis and antimicrobial investigation. Acta Chim. Slov., 56, 900–907 (2009a).
Rohini, R., Shanker, K., Reddy, P. M., Ho, Y. P., and Ravinder, V., Mono and bis-6-arylbenzimidazo[)1,2-c])quinazolines: a new class of antimicrobial agents. Eur. J. Med. Chem., 44, 3330–3339 (2009b).
Sakai, Y., Dobson, C., Diksic, M., Aubé, M., and Hamel, E., Sumatriptan normalizes the migraine attack-related increase in brain serotonin synthesis. Neurology, 70, 431–439 (2008).
Sarangapani, M. and Reddy, V. M., Pharmacological evaluation of 1-(N, N-disubstituted amino methyl)-3-imino-(2-phenyl-3,4-dihydro-4-oxo-quinazolin-3-yl)indolin-2-ones. Indian J. Pharm. Sci., 58, 147–149 (1996).
Shanker, K., Rohini, R., Reddy, P. M., Ho, Y. P., and Ravinder, V., Ru(II) complexes of N4 and N2O2 macrocyclic Schiff base ligands: their antibacterial and antifungal studies. Spectrochim. Acta A Mol. Biomol. Spectrosc., 73, 205–211 (2009).
Sharma, P., Kumar, A., and Pandey, P., A facile synthesis of N-phenyl-6-hydroxy-3-bromo-4-arylazo quinoline-2-ones under phase transfer catalytic conditions and studies on their antimicrobial activities. Indian J. Chem., 45B, 2077–2082 (2006).
Singh, G. S., Singh, T., and Lakhan, R., Synthesis 13C-NMR and anticonvulsant activity of new isatin-based spiroazetidinones. Indian J. Chem., 36B, 951–954 (1997).
Talbi, H., Humbert, B., and Billaud, D., Polyindole and poly (5-cyanoindole): electrochemical and FT-IR spectroscopic comparative studies. Synth. Met., 84, 875–876 (1997).
Tarafder, M. T. H., Kasbollah, A., Saravanan, N., Crouse, K. A., Ali, A. M., and Tin, O. K., S-methyldithiocarbazate and its Schiff bases: evaluation of bondings and biological properties. J. Biochem. Mol. Biol. Biophys., 6, 85–91 (2002).
Vicini, P., Geronikaki, A., Incerti, M., Busonera, B., Poni, G., Cabras, C. A., and La Colla, P., Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases. Bioorg. Med. Chem., 11, 4785–4789 (2003).
Yorikane, R., Mizuno, H., Itoh, Y., Koike, H., Miyake, S., Shiga, H., Kumakura, S., Fukami, M., Shimoji, Y., and Hashimoto, T., Antiarrhythmic and cardiovascular profiles of the fused indole compound (3aR,12R,12aR,12bS)-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxy isoquino [)2,1,8-lma])carbazol-5(1H)-one hydrochloride 1.5 hydrate. Arzneimittelforschung, 41, 1130–1136 (1991).
Zheng, M., Zheng, M., Ye, D., Deng, Y., Qiu, S., Luo, X., Chen, K., Liu, H., and Jiang, H., Indole derivatives as potent inhibitors of 5-lipoxygenase: design, synthesis, biological evaluation, and molecular modeling. Bioorg. Med. Chem. Lett. 17, 2414–2420 (2007).
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Rohini, R., Reddy, P.M., Shanker, K. et al. Synthesis of mono, bis-2-(2-arylideneaminophenyl) indole azomethines as potential antimicrobial agents. Arch. Pharm. Res. 34, 1077–1084 (2011). https://doi.org/10.1007/s12272-011-0705-z
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DOI: https://doi.org/10.1007/s12272-011-0705-z