Synthesis, spectral characterization and antimicrobial studies of new 3- and 4 - substituted in 7- aza indole derivatives

International Journal of PharmTech Research

Volumn 4, Issue 1, 2012, Pages 169-175

  Kumaran, K ^a   Raja Mohamed Kamil, S ^a   Jaisankar, K R ^a  

^a ISLAMIAH COLLEGE   (India)

Author keywords

1H pyrrolo 2, 3 b pyridine derivative; Anti microbial study; Zone of inhibition concentration

Indexed keywords

1 (4 MORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL) 3 (PYRIDINE 4 YL)THIOUREA; 1 (4 MORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL) 3 PHENYLTHIOUREA; 1 (TETRAHYDRO 2H PYRAN 4 YL) 3 (4 MORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)THIOUREA; 1 CYCLOHEXYL 3 (4 MORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)THIOUREA; 1 METHYL 3 (4 MORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)THIOUREA; 2 METHOXY N (4 THIOMORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)PYRIDINE 3 CARBOXAMIDE; 2 METHYL N (4 THIOMORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)PYRIDINE 3 CARBOXAMIDE; 5 METHYL N (4 THIOMORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)PYRIDINE 3 CARBOXAMIDE; INDOLE DERIVATIVE; N (4 MORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)THIAZOLE 4 CARBOXAMIDE; N (4 THIOMORPHOLINO 1H PYRROLO[2,3 B]PYRIDINE 3 YL)ACETAMIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANDIDA; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; KLEBSIELLA PNEUMONIAE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

EID: 84859981574     PISSN: None     EISSN: 09744304     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Xin Wang, Ben Zhi, et al., A practicle synthesis of 2-(1H-Pyrrolo[2,3-b]pyridine-4yl) methylamino)-5-fluoronicotinic Acid., J. Org. Chem. 2006,71, 4021-4023.
2. Terence A. Kelly, Novel Non-Nucleoside Inhibitors of Human Immunodeficiency virus Type 1 reverse Transcriptase. 6. 2-indol-3-yl and 2-azaindol-3-yl dipyridodiazepinoones, J. Med. Chem. 1997, 40, 2430-2433.
3. US Patent: PCT/US2006/062453; WO 2007/076423.
4. John J. Caldwell, Kwai-Ming Cheung and Ian Collins., Synthesis of 4-(cyclic dialkylamino)-7-azaindoles by microwave heating of 4-halo-7-azaindoles and cyclic secondary amines, Tetrahedron Letters 48 (2007) 1527-1529.
5. ARRAY BIOPHARMA INC., Publ.; WO2009/140320 A1 (2009/11/19), Appl.; WO2009-US43691 (2009/05/13).
6. Florence Popowycz, Sylvain Routier, Benoît Joseph, Jean-Yves Mérour, Synthesis and reactivity of 7-azaindole (1H-pyrrolo [2,3-b]pyridine, Review Tetrahedron, Volume 63, Issue 5, 29 January 2007, Pages 1031-1064.
7. Santiago Figueroa-Pérez, Samir Bennabi, Hartmut Schirok, Michael Thutewohl, Efficient synthesis of 4-O-and C-substituted-7-azaindoles, Tetrahedron Letters, Volume 47, Issue 13, 27 March 2006, Pages2069-2072.
8. Alexandre L'Heureux, Carl Thibault, Réjean Ruel, Synthesis of functionalized 7-azaindoles via directed ortho-metalations, Tetrahedron Letters, Volume 45, Issue 11, 8 March 2004, Pages 2317-2319.
9. G. Lavecchia, S. Berteina-Raboin, G. Guillaumet, Synthesis and functionalisation of 1Hpyrazolo[3,4-b]pyridines involving copper and palladium-promoted coupling reactions, Tetrahedron Letters, Volume 45, Issue 11, 8 March 2004, Pages 2389-2392.
10. Axel R. Stoit, Arnold P. den Hartog, Harry Mons, Sjoerd van Schaik, Nynke Barkhuijsen, Cees Stroomer, Hein K. A. C. Coolen, Jan Hendrik Reinders, Tiny J. P. Adolfs, Martina van der Neut, Hiskias Keizer, Chris G. Kruse, 7-Azaindole derivatives as potential partial nicotinic agonists, Bioorg. Med. Chem. Lett. 18, (2008) 188-193.
11. G. Lavecchia, S. Berteina-Raboin, G. Guillaumet, Synthesis and functionalisation of 1Hpyrazolo[3,4-b]pyridines involving copper and palladium-promoted coupling reactions, Tetrahedron Letters, Volume 45, Issue 11, 8 March 2004, Pages 2389-2392.
12. Niels Krogsgaard-Larsen, Mikael Begtrup, Karla Frydenvang, Jan Kehler, Syntheses of azaanalogous iso-ergoline scaffolds using carbene mediated C-H insertion, Tetrahedron, Volume 66, Issue 47, 20 November 2010, Pages 9297-9303.
13. Jérome Guillard, Maÿlis Decrop, Nathalie Gallay, Claire Espanel, Elodie Boissier, Olivier Herault and Marie-Claude Viaud-Massuard, Synthesis and biological evaluation of 7-azaindole derivatives, synthetic cytokinin analogues, Bioorganic & Medicinal Chemistry Letters, Volume 17, Issue 7, 1 April 2007, Pages 1934-1937.
14. Santiago Figueroa-Pérez, Samir Bennabi, Hartmut Schirok, Michael Thutewohl, Efficient synthesis of 4-O-and C-substituted-7-azaindoles, Tetrahedron Letters, Volume 47, Issue 13, 27 March 2006, Pages 2069-2072.
15. Abderaouf Ahaidar, David Fernández, Olga Pérez, Gerardo Danelón, Carmen Cuevas, Ignacio Manzanares, Fernando Albericio, John A. Joule, Mercedes Álvarez, Synthesis of variolin B, Tetrahedron Letters, Volume 44, Issue 33, 11 August 2003, Pages 6191-6194.
16. John Liddle, Paul Bamborough, Michael D. Barker, Sebastien Campos, Rick P. C. Cousins, Geoffrey J. Cutler, Heather Hobbs, Duncan S. Holmes, Chris Ioannou, Geoff W. Mellor, Mary A. Morse, 4-Phenyl-7-azaindoles as potent and selective IKK2, inhibitors, Bioorganic & Medicinal Chemistry Letters, Volume 19, Issue 9, 1 May 2009, Pages 2504-2508.
17. Sylvain Routier, Nathalie Ayerbe, Jean-Yves Mérour, Gérard Coudert, Christian Bailly, Alain Pierré, Bruno Pfeiffer, Daniel-Henri Caignard, Pierre Renard, Synthesis and biological evaluation of 7-azaindolocarbazoles; Tetrahedron, Volume 58, Issue 33, 12 August 2002, Pages 6621-6630.
18. Gee-Hong Kuo, Catherine Prouty, Alan DeAngelis, Lan Shen, David J. O'Neill, Chandra Shah, Peter J. Connolly, William V. Murray, Bruce R. Conway, Peter Cheung, Lori Westover, Jun Z. Xu, Richard A. Look, Keith T. Demarest, Stuart Emanuel, Steven A. Middleton, Linda Jolliffe, Mary Pat Beavers, and Xin Chen., Synthesis and Discovery of Macrocyclic Polyoxygenated Bis-7-azaindolylmaleimides as a Novel Series of Potent and Highly Selective Glycogen Synthase Kinase-3β Inhibitors, J. Med. Chem., 2003, 46 (19), pp 4021-4031.
19. Antonella Ermoli, Alberto Bargiotti, Maria Gabriella Brasca, Antonella Ciavolella, Nicoletta Colombo, Gabriele Fachin, Antonella Isacchi, Maria Menichincheri, Antonio Molinari, Alessia Montagnoli, Antonio Pillan, Sonia Rainoldi, Federico Riccardi Sirtori, Francesco Sola, Sandrine Thieffine, Marcellino Tibolla, Barbara Valsasina, Daniele Volpi, Corrado Santocanale and Ermes Vanotti, Cell Division Cycle 7 Kinase Inhibitors: 1H-Pyrrolo[2,3-b]pyridines, Synthesis and Structure-Activity Relationships, J. Med. Chem., 2009,52 (14), pp 4380-4390.
20. Terrine K. Adler, Adrien Albert. The Biological and Physical Properties of the Azaindoles, J. Med. Chem., 1963, 6 (5), pp 480-483.
21. Tao Wang, Zhongxing Zhang, Owen B. Wallace, Milind Deshpande, Discovery of 4-Benzoyl-1-[(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine (BMS-378806): A Novel HIV-1 Attachment Inhibitor That Interferes with CD4-gp120 Interactions, J. Med. Chem., 2003, 46 (20), pp 4236-4239.
22. Merour, J. Y.; Joseph, B, Curr. Org. Chem. 2001, 5, 471 and reference cited therein.
23. Carl Thibault, Alexandre L Heureux, Rajeev S. Bhide, and Rejean Ruel., Concise and Efficient Synthesis of 4-Fluoro-1H-pyrrolo[2,3-b]pyridine.
24. John J. Caldwell, Kwai-Ming Cheung and Ian Collins., Synthesis of 4-(cyclic dialkylamino)-7-azaindoles by microwave heaing of 4-halo-7-azaindoles and cyclic secondary amines. Tetrahedron Letters 48 (2007) 1527-1529.
25. Perez, C., Pauli, M., Bazerque, P. 1990. An antibiotic assay by the agar-well diffusion method. Acta Biol. Med. Exp., 15: 13-115.
26. Bagamboula, C. F., Uyttendaele, M., Debevere, J. 2004. Inhibitory effect of thyme and basil essential oils, carvacrol, thymol, estragol, linalool and pcymene towards Shigella sonnei and S. flexneri. Food Microbiol, 21: 33-42.
27. Erdemoǧlu, N., Kü Peli, E., Yes, E., Ilada, R. 2003. Anti-inflammatory and antinociceptive activity assessment of plants used as remedy in Turkish folk medicine. J. Ethnopharmacol., 89: 123-1.
28. Perez, C., Pauli, M., Bazerque, P. 1990. An antibiotic assay by the agar-well diffusion method. Acta Biol. Med. Exp., 15: 13-115.