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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

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Volume 62, Issue 1 (Mar 2012)

Issues

Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles

Adel Mandour / Eslam El-Sawy / Manal Ebaid / Seham Hassan
  • Department of Drug Radiation Research, National Centre for Radiation Research and Technology, Cairo, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2012-04-03 | DOI: https://doi.org/10.2478/v10007-012-0007-0

Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles

Starting from N-substituted indole-3-carboxaldehydes (1a-g) a series of new 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles (3a-g and 4a-g) have been synthesized via the acid catalyzed condensation reaction of 1a-g with 3-amino-5-pyrazolone, followed by the reaction with arylidene malononitriles. A series of new 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles (7a-g) have been prepared either via the base catalyzed condensation reaction of 1a-g with 3-amino-5-pyrazolone to give 6a-g, followed by the reaction with malononitrile or by the reaction of N-substituted-3-indolylidene malononitriles (5a-g) with 3-amino-5-pyrazolone. According to the obtained results, the newly synthesized compounds possess significant anti-inflammatory, analgesic and anticonvulsant activities. The anticonvulsant potency of certain tested compounds was more pronounced than both anti-inflammatory and analgesic activities. Moreover, most of the newly synthesized compounds possess potential antimicrobial activity against Escherichia coli and Pseudomonas aeruginosa.

Sinteza i potencijalno biološko djelovanje novih 3-((N-supstituiranih indol-3-il)metilenamino)-6-amino-4-aril-pirano(2,3-c)pirazol-5-karbonitrila i 3,6-diamino-4-(N-supstituiranih indol-3-il)pirano(2,3-c)pirazol-5-karbonitrila

U radu se opisuje sinteza novih 3-[N-supstituiranih indol-3-il)metilenamino]6-amino-4-aril-pirano(2,3-c) pirazol-5-karbonitrila (3a-g i 4a-g) kiselo-kataliziranom kondenzacijom N-supstituiranih indol-3-karboksaldehida (1a-g) s 3-amino-5-pirazolonom iza koje slijedi reakcija s ariliden malononitrilom. Serija novih 3,6-diamino-4-(N-supstituiranih indol-3-il)pirano(2,3-c)pirazol-5-karbonitrila (7a-g) sintetizirana je reakcijom malononitrila s produktima 6a-g, koji su pripravljeni bazno-kataliziranom kondenzacijom 1a-g s 3-amino-5-pirazolonom. Neki spojevi iz serije 7a-g dobiveni su reakcijom N-supstituiranih 3-indolidin malononitrila (5a-g) s 3-amino-5-pirazolonom. Novosintetizirani spojevi imaju značajno protuupalno, analgetsko i antikonvulzivno djelovanje. Antikonvulzivno djelovanje pojedinih testiranih spojeva bilo je jače izraženo nego protuupalno i analgetsko djelovanje. Većina ispitivanih spojeva pokazuje antimikrobno djelovanje na Escherichia coli i Pseudomonas aeruginosa.

Keywords: indole; pyrano(2,3-c)pyrazole; anti-inflammatory; analgesic; anticonvulsant; antimicrobial activity

Keywords: indol; pirano(2,3-c)pirazol; protuupalno; analgetsko; antikonvulzivno; antimikrobno djelovanje

  • P. Rani, V. K. Srivastava and A. Kumar, Synthesis and anti-inflammatory activity of heterocyclic indole derivatives, Eur. J. Med. Chem. 39 (2004) 449-452; DOI: 10.1016j.egmech2003.11.002.Google Scholar

  • M. Amir, S. A. Javed and H. Kumar, Synthesis and biological evaluation of some 4-(1H-indol-3-yl)-6-phenyl-1,2,3,4-tetrahydropyrimidin-2-ones/thiones as potent anti-inflammatory agents, Acta Pharm. 58 (2008) 467-477; DOI: 10.2478/v10007-008-0028-x.PubMedCrossrefGoogle Scholar

  • A. H. Mandour, E. R. El-Sawy, K. H. Shaker and M. A. Mustafa, Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of 1,8-dihydro-1-aryl-8-alkyl pyrazolo(3,4-b)indole, Acta Pharm. 60 (2010) 73-88; DOI: 10.2478/v10007-010-0009-8.CrossrefPubMedGoogle Scholar

  • N. Siddiqui, M. S. Alam and W. Ahsan, Synthesis, anticonvulsant and toxicity evaluation of 2-(1H-indol-3-yl)acetyl-N-(substituted phenyl) hydrazine carbothioamides and their related heterocyclic derivatives, Acta Pharm. 58 (2008) 445-454; DOI:10.2478/v10007-008-0025-0.PubMedCrossrefWeb of ScienceGoogle Scholar

  • M. A. A. Radwan, E. A. Ragab, N. M. Sabrya and S. M. El-Shenawy, Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents, Bioorg. Med. Chem. 15 (2007) 3832-3841; DOI: 10.1016/j.bmc.2007.03.024.CrossrefGoogle Scholar

  • E. R. El-Sawy, F. A. Bassyouni, S. H. Abu-Bakr, H. M. Rady and M. M. Abdlla, Synthesis and biological activity of some new 1-benzyl and 1-benzoyl 3-heterocyclic indole derivatives, Acta Pharm. 60 (2010) 55-71; DOI: 10.2478/v10007-010-0004-0.PubMedCrossrefGoogle Scholar

  • S. George, M. P. Waran, A. Chakraborty and T. K. Ravi, Synthesis and evaluation of the biological activities of some 3-[5-(6-methyl-4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-oxadiazol-2-yl]-imino-1,3-di-hydro-2H-indol-2-one derivatives, Acta Pharm. 58 (2008) 119-129; DOI: 10.2478/v10007-007-0050-4.CrossrefGoogle Scholar

  • M. E. Zaki, H. A. Soliman, O. A. Hiekal and A. E. Z. Rashad, Pyrazolopyranopyrimidines as a class of anti-inflammatory agents, Z. Naturforsch. C 61 (2006) 1-5.Google Scholar

  • S. G. Kuo, L. J. Huang and H. Nakamura, Studies on heterocyclic compounds. 6. Synthesis and analgesic and anti-inflammatory activities of 3,4-dimethylpyrano[2,3-c]pyrazol-6-one derivatives, J. Med. Chem. 27 (1984) 539-544.Google Scholar

  • R. M. Abd El-Aal and M. Younis, Synthesis and antimicrobial activity of certain novel monomethine cyanine dyes, Dyes Pigments 60 (2004) 205-214; DOI: 10.1016/S0143-7208(03)00131-1.CrossrefGoogle Scholar

  • H. M. Al-Matar, K. D. Khalil, A. Y. Adam and M. H. Elnagdi, Green one pot solvent-free synthesis of pyrano[2,3-c]-pyrazoles and pyrazolo[1,5-a]pyrimidines, Molecules 15 (2010) 6619-6629; DOI: 10.3390/molecules15096619.Web of ScienceCrossrefGoogle Scholar

  • A. M. Shestopalov, A. P. Yakubov, D. V. Tsyganov, E. Yanova, M. Yu and V. N. Nesterov, One-pot synthesis of diverse 4-di(tri)fluoromethyl-3-cyanopyridine-2(1H)-thiones and their utilities in the cascade synthesis of annulated heterocycles, Chem. Heterocyc. Compd. 38 (2002) 1180-1189; DOI: 10.1021/cc7001793.CrossrefGoogle Scholar

  • S. Gogoi and C. Zhao, Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazole, Tetrahedron Lett. 50 (2009) 2252-2255; DOI: 10.1016/j.tetlet.2009.02.210.CrossrefGoogle Scholar

  • A. L. Mndzhoyan, G. L. Papayan, L. D. Zhuruli, S. G. Karagezyan, L. S. Galstyan and V. G. Sarafyan, Synthesis and biological study of hydrazinohydrazones of indole aldehydes and ketons series, Arm. Khim. Zh. (USSR) 22 (1969) 707-713; ref. Chem. Abstr. 72 (1970) 11189f.Google Scholar

  • A. H. Mandour, E. R. El-Sawy, M. A. Zahran, M. S. Ebaid and M. A. Mustafa, Anti-inflammatory, analgesic, anticonvulsant and antimicrobial activities of some new synthesized N-alkyl-3-indolyl pyrimidines and benzimidazolo(1,2-a) pyrimidines, Biohealth Sci. Bull. (Malaysia) 1 (2009) 57-67.Google Scholar

  • M. G. Obukowicz, D. J. Welsch, W. J. Salsgiver, M. Berger, K. S. Chinn and K. L. Duffin, Novel, selective delta6 or delta5 fatty acid desaturase inhibitors as anti-inflammatory agents in mice, J. Pharmacol. Exp. Ther. 287 (1998) 157-162.Google Scholar

  • C. A. Winter, E. A. Risely and G. W. Nuss, Anti-infalmmatory and antipyretic activities of indomethacin, 1-(p-chlorobenzyl)-5-methoxy-2-methyl-indole-3-acetic acid, J. Pharmacol. Exp. Ther. 141 (1963) 369-376.Google Scholar

  • R. Okun, S. C. Liddon and L. Lasagna, Effect of reserpine pre-treatment on the protective action of amphetamine and phenoxy propazine in the phenylbenzoquinone-induced writhing syndrome in mice, J. Pharm. Exp. Ther. 139 (1963) 107-110; DOI: 10.1038/201306a0.CrossrefGoogle Scholar

  • Drug Discovery and Evaluation: Pharmacological Assays, Chapter E: Psychotropic and Neurotropic Activity (Eds. H. G. Vogel and W. H. Vogel, Springer-Verlag), Berlin 1997, pp. 260-261.Google Scholar

  • A. L. Barry and C. Thornsberry, Susceptibility Testing: Diffusion Test Procedures, in Manual of Clinical Microbiology (Eds. E. H. Lennette, A. Balows, W. J. Hausler, Jr. and J. P. Truant), 3rd ed., American Society for Microbiology, Washington (DC) 1980, pp. 463-474.Google Scholar

About the article


Published Online: 2012-04-03

Published in Print: 2012-03-01


Citation Information: Acta Pharmaceutica, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: https://doi.org/10.2478/v10007-012-0007-0.

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