Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity
English
Effi cient and mild cyclization procedures for the synthesis of novel 2-amino-4H-pyran derivatives with potential antitumor activity
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Key words:
- Synthesis
- / 2-Amino-4H-pyran derivatives
- / Multicomponent
- / Anticancer
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[1] N. Sultana, P.G. Waterman, 3-Monoterpenyl-2,4-deoxygenated quinoline alkaloids from the aerial parts of Halfordia kendack, Phytochemistry 58 (2001) 329-332.[1] N. Sultana, P.G. Waterman, 3-Monoterpenyl-2,4-deoxygenated quinoline alkaloids from the aerial parts of Halfordia kendack, Phytochemistry 58 (2001) 329-332.
-
[2] K. Nakashima, M. Oyama, T. Ito, et al., Melicodenines A and B, novel Diels-Alder type adducts isolated from Melicope denhamii, Tetrahedron Lett. 52 (2011) 4694-4696.[2] K. Nakashima, M. Oyama, T. Ito, et al., Melicodenines A and B, novel Diels-Alder type adducts isolated from Melicope denhamii, Tetrahedron Lett. 52 (2011) 4694-4696.
-
[3] K. Nakashima, M. Oyama, T. Ito, et al., Novel quinolinone alkaloids bearing a lignoid moiety and related constituents in the leaves of Melicope denhamii, Tetrahedron 68 (2012) 2421-2428.[3] K. Nakashima, M. Oyama, T. Ito, et al., Novel quinolinone alkaloids bearing a lignoid moiety and related constituents in the leaves of Melicope denhamii, Tetrahedron 68 (2012) 2421-2428.
-
[4] I.S. Chen, I.W. Tsai, C.M. Teng, et al., Pyranoquinoline alkaloids from Zanthoxylum simulans, Phytochemistry 46 (1997) 525-529.[4] I.S. Chen, I.W. Tsai, C.M. Teng, et al., Pyranoquinoline alkaloids from Zanthoxylum simulans, Phytochemistry 46 (1997) 525-529.
-
[5] M. Isaka, M. Tanticharoen, P. Kongsaeree, et al., Structures of cordypyridones A-D, antimalarial N-hydroxy-and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica, J. Org. Chem. 66 (2001) 4803-4808.[5] M. Isaka, M. Tanticharoen, P. Kongsaeree, et al., Structures of cordypyridones A-D, antimalarial N-hydroxy-and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica, J. Org. Chem. 66 (2001) 4803-4808.
-
[6] C.L. Cantrell, K.K. Schrader, L.K. Mamonov, et al., Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii, J. Agric. Food Chem. 53 (2005) 7741-7748.[6] C.L. Cantrell, K.K. Schrader, L.K. Mamonov, et al., Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii, J. Agric. Food Chem. 53 (2005) 7741-7748.
-
[7] A.U. Rahman, A. Khalid, N. Sultana, et al., New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids, J. Enzyme Inhib. Med. Chem. 21 (2006) 703-710.[7] A.U. Rahman, A. Khalid, N. Sultana, et al., New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids, J. Enzyme Inhib. Med. Chem. 21 (2006) 703-710.
-
[8] P.L. Katavic, D.A. Venables, G.P. Guymer, et al., Alkaloids with human delta-opioid receptor binding affinity from the Australian rainforest tree Peripentadenia mearsii, J. Nat. Prod. 70 (2007) 1946-1950.[8] P.L. Katavic, D.A. Venables, G.P. Guymer, et al., Alkaloids with human delta-opioid receptor binding affinity from the Australian rainforest tree Peripentadenia mearsii, J. Nat. Prod. 70 (2007) 1946-1950.
-
[9] I.S. Chen, S.J. Wu, I.L. Tsai, et al., Chemical and bioactive constituents from zanthoxylum simulans, J. Nat. Prod. 57 (1994) 1206-1211.[9] I.S. Chen, S.J. Wu, I.L. Tsai, et al., Chemical and bioactive constituents from zanthoxylum simulans, J. Nat. Prod. 57 (1994) 1206-1211.
-
[10] K.D. McBrien, Q. Gao, S. Huang, et al., Fusaricide, a new cytotoxic N-hydroxypyridone from Fusarium sp., J. Nat. Prod. 59 (1996) 1151-1153.[10] K.D. McBrien, Q. Gao, S. Huang, et al., Fusaricide, a new cytotoxic N-hydroxypyridone from Fusarium sp., J. Nat. Prod. 59 (1996) 1151-1153.
-
[11] R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles, Bioorg. Med. Chem. Lett. 17 (2007) 6459-6462.[11] R.R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles, Bioorg. Med. Chem. Lett. 17 (2007) 6459-6462.
-
[12] M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, et al., Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5, 6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101), J. Med. Chem. 53 (2010) 7180-7191.[12] M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, et al., Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5, 6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101), J. Med. Chem. 53 (2010) 7180-7191.
-
[13] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, et al., An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate, Chin. Chem. Lett. 24 (2013) 901-903.[13] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, et al., An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate, Chin. Chem. Lett. 24 (2013) 901-903.
-
[14] N. Foroughifar, S. Ebrahimi, One-pot synthesis of 1,3-thiazolidin-4-one using Bi(SCH2COOH)3 as catalyst, Chin. Chem. Lett. 24 (2013) 389-391.[14] N. Foroughifar, S. Ebrahimi, One-pot synthesis of 1,3-thiazolidin-4-one using Bi(SCH2COOH)3 as catalyst, Chin. Chem. Lett. 24 (2013) 389-391.
-
[15] R. Baharfar, S.M. Baghbanian, Synthesis of novel uracil based 2,5-diaminofurans using multi-component reactions, Chin. Chem. Lett. 23 (2012) 677-680.[15] R. Baharfar, S.M. Baghbanian, Synthesis of novel uracil based 2,5-diaminofurans using multi-component reactions, Chin. Chem. Lett. 23 (2012) 677-680.
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[16] S.L. Wang, Z.G. Han, S.J. Tu, et al., An efficient method for synthesis of pyrano[3,2-c]pyridine derivatives under microwave irradiation, J. Heterocyclic Chem. 46 (2009) 828-831.[16] S.L. Wang, Z.G. Han, S.J. Tu, et al., An efficient method for synthesis of pyrano[3,2-c]pyridine derivatives under microwave irradiation, J. Heterocyclic Chem. 46 (2009) 828-831.
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[17] Crystallographic data (excluding structure factors) for compound 4a have been deposited with the Cambridge Crystallographic Data Center.[17] Crystallographic data (excluding structure factors) for compound 4a have been deposited with the Cambridge Crystallographic Data Center.
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