Citation: E. Rajanarendar, K. Thirupathaiah, S. Ramakrishna, D. Nagaraju. A facile and convenient synthesis of novel imidazo[1,2-b] isoxazoles and their Mannich bases as potential biodynamic agents[J]. Chinese Chemical Letters, ;2015, 26(12): 1511-1513. doi: 10.1016/j.cclet.2015.07.024
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A series of novel imidazo[1,2-b]isoxazoles 3 and their Mannich bases 4-6 were synthesized via convenient reactions. The reaction of 3-aminoisoxazole 1 with substituted phenacyl bromides 2 in dry ethanol afforded the corresponding 6-methyl-3-aryl imidazo[1,2-b]isoxazoles 3 in good yields. Compounds 3 on treatment with 37% formaline and secondary amines furnished the corresponding novel Mannich bases viz., 6-methyl-3-aryl-2-(morpholine/pyrrolidin-1-yl/piperidin-1-yl)-methyl-imidazo[ 1,2-b]isoxazoles 4-6.
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Keywords:
- Imidazo[1,2-b]isoxazoles
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[1]
[1] E.M. Guantai, K. Ncokazi, T.J. Egan, et al., Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds, Bioorg. Med. Chem. 18 (2010) 8243-8256.
-
[2]
[2] C.A. Fraga, Drug hybridization strategies: before or after lead identification? Expert Opin. Drug Discov. 4 (2009) 605-609.
-
[3]
[3] F. Bellina, S. Cauteruccio, S. Montib, R. Rossi, Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modelling study of their binding to the colchicines site of tubulin, Bioorg. Med. Chem. Lett. 16 (2006) 5757-5762.
-
[4]
[4] J.Z. Vlahakis, M. Humb, M.N. Rahman, et al., Synthesis and evaluation of imidazole- dioxolane compounds as selective heme oxygenase inhibitors: Effect of substituents at the 4-position of the dioxolane ring, Bioorg. Med. Chem. 17 (2009) 2461-2475.
-
[5]
[5] K. Bhandari, N. Srinivas, V.K. Marrapu, A. Verma, S. Srivastava, S. Gupta, Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents, Bioorg. Med. Chem. Lett. 20 (2010) 291-293.
-
[6]
[6] K. Hanazaki, P. Gupta, S.K. Singh, et al., Current antiviral therapy for chronic hepatitis C including liver transplantation and hepatic resection, Curr. Med. Chem. 2 (2003) 103-111.
-
[7]
[7] K. Bleicher, F. Gerber, Y. Wuthrich, A. Alanine, A. Capretta, Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols, Tetrahedron Lett. 43 (2002) 7687-7690.
-
[8]
[8] (a) G. Trapani, M. Franco, A. Latrofa, et al., Derivatives of imidazole. III. Synthesis and pharmacological activities of nitriles, amides, and carboxylic acid derivatives of imidazo[[1,2-a] pyridines, J. Med. Chem. 42 (1999) 3934-3937; (b) G.J. George, D.P. Vercauteren, G.H. Evard, et al., Characterization of the physicchemical properties of the imidazopyridine derivative Alpidem, Comparison with Zolpidem, Eur. J. Med. Chem. 28 (1993) 323-325.
-
[9]
[9] S.M. Reilly, E.S. Newlands, M.G. Glaser, et al., Temozolomide: A new oral cytotoxic chemotherapeutic agent with promising activity against primary brain tumors, Eur. J. Cancer 29A (1993) 940-942.
-
[10]
[10] H.S. Friedman, T. Kerby, H. Calvert, Temozolomide and treatment of malignant glioma, Clin. Cancer Res. 6 (2000) 2585-2597.
-
[11]
[11] T. Batchelor, Primary nervous-system lymphoma, Lancet 355 (2000) 354-365.
-
[12]
[12] J. Getal, Synthesis of 3-[1,3-thazol-2-yl-] as potential antitumor agents, Antibiotics 28 (1975) 91-94.
-
[13]
[13] C.H. Eugster, Chemie der wirkstoffe aus dem fliegenpilz (amanita muscaria), Prog. Chem. Org. Nat. Prod. 27 (1969) 261.
-
[14]
[14] H. Kano, I. Adachi, R. Kido, K. Hirose VIII., Synthesis and pharmacological properties of 5-aminoalkyl- and 3-aminoalkylisoxazoles and related derivatives, J. Med. Chem. 10 (1967) 411-418.
-
[15]
[15] P.B. Reddy, S.M. Reddy, E. Rajanarendar, A.K. Murthy, Antifungal activity of isoxazolyl thiazolidin-4-ones, Indian Phytopathol. 37 (1984) 369-398.
-
[16]
[16] M.T. Chemicals, K.K. Mitsui, Seiyaku kogyoo, vol. 6, Toyama Chemical Co. Ltd., 1994p. 146.
-
[17]
[17] E.T. Marquis, J.R. Sanderson, US Patent 528335 (1994), Chem. Abstr. 120 (1994) 217649.
-
[18]
[18] Streling Drug. Inc., US Patent (1988) 4755595, Chem. Abstr. 110 (1989) 730.
-
[19]
[19] A. Sadanadam, M.V. Rajam, K. Subash, E. Rajanarendar, Production of chromosomal breaks by isoxazolyl thiazolidin-one in allium sativu, Indian Bot. Rep. 3 (1984) 38-42.
-
[20]
[20] F. Palagiano, L. Arenare, E. Luraschi, et al., Research on heterocyclic compounds XXXIV. Synthesis and SAR study of some imidazo[2,1-b] thiazole carboxylic and acetic acids with anti-inflammatory and analgesic activity, Eur. J. Med. Chem. 30 (1995) 901-909.
-
[21]
[21] S. Kamila, K. Mendoza, E.R. Biehl, Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-16-phenylimidazo[2, 1-b] thiazole-5-yl)-thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazole-5-yl)ethenones and thioureas, Tetrahedron Lett. 53 (2012) 4921-4924.
-
[22]
[22] (a) E. Rajanarendar, S. Ramakrishna, K. Ramamurthy, Synthesis of novel isoxazolyl bis-thiazolo[3,2-a]pyrimidines, Chin. Chem. Lett. 23 (2012) 899-902; (b) E. Rajanarendar, S. Ramakrishna, K. Govardhan Reddy, D. Nagaraju, Y.N. Reddy, A facile synthesis, anti-inflammatory and analgesic activity of isoxazolyl- 2,3-dihydrospiro [benzo[f]isoindole-1,3'-indoline]-2',4,9-triones, Bioorg. Med. Chem. Lett. 23 (2013) 3954-3958; (c) E. Rajanarendar, K. Govardhan Reddy, S. Rama Krishna, et al., Synthesis and in vitro and in vivo anticancer activity of novel 3-methyl-5H-isoxazolo[ 5'4;:5,6]pyrido[2,3-b]indoles, Bioorg. Med. Chem. Lett. 22 (2012) 6677-6680; (d) E. Rajanarendar, G. Mohan, E. Kalyan Rao, M. Srinivas, Palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of organo boronic acids with N-protected 4-iodophenyl alanine linked isoxazoles, Chin. Chem. Lett. 1 (2009) 1-4; (e) E. Rajanarendar, A. Siva Rami Reddy, S. Raju, S. Firoz Pasha, K. Govardhan Reddy, A fast and highly efficient protocol for reductive amination of aromatic aldehydes using NaBH4 and isoxazole amines in an ionic liquid medium, Chin. J. Chem. 29 (2011) 769-772.
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