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Volumn 14, Issue 10, 2012, Pages 551-557

One-pot access to a library of structurally diverse nicotinamide derivatives via a three-component formal Aza [3 + 3] cycloaddition

Author keywords

3 + 3 aza annulations; Multicomponent reactions; Pyridine synthesis

Indexed keywords

ACETIC ACID DERIVATIVE; AMIDE; AMMONIUM ACETATE; BETA KETOAMIDE; BETA-KETOAMIDE; CHALCONE DERIVATIVE; NICOTINAMIDE;

EID: 84870284565     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300081k     Document Type: Article
Times cited : (38)

References (35)
  • 1
    • 3042558198 scopus 로고    scopus 로고
    • De novo synthesis of substituted pyridines
    • DOI 10.1016/j.tet.2004.04.043, PII S0040402004005939
    • Henry, G. D. De novo synthesis of substituted pyridines. Tetrahedron 2004, 60, 6043-6061. (Pubitemid 38824592)
    • (2004) Tetrahedron , vol.60 , Issue.29 , pp. 6043-6061
    • Henry, G.D.1
  • 2
    • 35348959557 scopus 로고    scopus 로고
    • The Bohlmann-Rahtz pyridine synthesis: From discovery to applications
    • DOI 10.1055/s-2007-986674
    • Bagley, M.C; Glover, C.; Merritt, E. A. The Bohlmann-Rahtz pyridine synthesis: From discovery to applications. Synlett 2007, 2459-2482. (Pubitemid 47597146)
    • (2007) Synlett , Issue.16 , pp. 2459-2482
    • Bagley, M.C.1    Glover, C.2    Merritt, E.A.3
  • 3
    • 78249271716 scopus 로고    scopus 로고
    • Recent strategies for the synthesis of pyridine derivatives
    • Hill, M. D. Recent strategies for the synthesis of pyridine derivatives. Chem. - Eur. J. 2010, 16, 12052-12062.
    • (2010) Chem. - Eur. J , vol.16 , pp. 12052-12062
    • Hill, M.D.1
  • 4
    • 77952477596 scopus 로고    scopus 로고
    • R privileged scaffolds for library design and drug discovery
    • Welsch, M. E.; Snyder, S. A; Stockwell, B. R Privileged scaffolds for library design and drug discovery. Curr. Opin. Chem. Biol. 2010, 14, 347-361.
    • (2010) Curr. Opin. Chem. Biol , vol.14 , pp. 347-361
    • Welsch, M.E.1    Snyder, S.A.2    Stockwell, B.3
  • 5
    • 15244355745 scopus 로고    scopus 로고
    • + cosubstrate specificity of a Sir2 enzyme
    • DOI 10.1016/j.molcel.2005.02.022
    • + cosubstrate specificity of a Sir2 enzyme. Mol. Cell 2005, 17, 855-868. (Pubitemid 40386946)
    • (2005) Molecular Cell , vol.17 , Issue.6 , pp. 855-868
    • Avalos, J.L.1    Bever, K.M.2    Wolberger, C.3
  • 6
    • 0041743805 scopus 로고    scopus 로고
    • Nicorandil: A drug for many purposes: Too good to be true?
    • DOI 10.1016/S0195-668X(03)00318-X
    • Eeckhout, E. Nicorandil: A drug for many purposes. Too good to be true? Eur. Heart J. 2003, 24, 1282-1284. (Pubitemid 36917697)
    • (2003) European Heart Journal , vol.24 , Issue.14 , pp. 1282-1284
    • Eeckhout, E.1
  • 7
    • 19444362093 scopus 로고    scopus 로고
    • Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: A potent and orally bioavailable NCX inhibitor
    • DOI 10.1016/j.bmc.2005.03.052, PII S0968089605002774
    • Kuramochi, T.; Kakefuda, A.; Yamada, H; Tsukamoto, I.; Taguchi, T.; Sakamoto, S. Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivate: A potent and orally bioavailable NCX inhibitor. Bioorg. Med. Chem. 2005, 13, 4022-4036. (Pubitemid 40725034)
    • (2005) Bioorganic and Medicinal Chemistry , vol.13 , Issue.12 , pp. 4022-4036
    • Kuramochi, T.1    Kakefuda, A.2    Yamada, H.3    Tsukamoto, I.4    Taguchi, T.5    Sakamoto, S.6
  • 8
    • 0038778278 scopus 로고    scopus 로고
    • Discovery of substituted N-phenyl nicotinamides as potent inducers of apoptosis using a cell- and caspase-based high throughput screening assay
    • DOI 10.1021/jm0205200
    • Cai, S. X.; Nguyen, B.; Jia, S.; Guastella, J.; Reddy, S.; Tseng, B.; Drewe, J.; Kasibhatla, S. Discovery of substituted N-phenyl nicotinamide as potent inducers of apoptosis using a cell- and caspase-based high throughput screening assay. J. Med. Chem. 2003, 46, 2474-2481. (Pubitemid 36637931)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.12 , pp. 2474-2481
    • Cai, S.X.1    Nguyen, B.2    Jia, S.3    Herich, J.4    Guastella, J.5    Reddy, S.6    Tseng, B.7    Drewe, J.8    Kasibhatla, S.9
  • 9
    • 80054788763 scopus 로고    scopus 로고
    • BRN-103, A novel nicotinamide derivative, inhibits VEGF-induced angiogenesis and proliferation in human umbilical vein endothelial cells
    • Choi, H. E.; Yoo, M. S.; Lee, J. H; Kim, J. H; Kim, J. H; Lee, J. K.; Kim, G I.; Park, Y.; Chi, Y. H; Paik, S. H; Lee, J. H. BRN-103, A novel nicotinamide derivative, inhibits VEGF-induced angiogenesis and proliferation in human umbilical vein endothelial cells. Bioorg. Med. Chem. 2011, 21, 6236-6241.
    • (2011) Bioorg. Med. Chem , vol.21 , pp. 6236-6241
    • Choi, H.E.1    Yoo, M.S.2    Lee, J.H.3    Kim, J.H.4    Kim, J.H.5    Lee, J.K.6    Kim G, I.7    Park, Y.8    Chi, Y.H.9    Paik, S.H.10    Lee, J.H.11
  • 10
    • 79953077013 scopus 로고    scopus 로고
    • Positive allosteric modulators of type 5 metabotropic glutamate receptors (mGlur5) and their therapeutic potential for the treatment of CNS disorders
    • Cleva, R M; Foster Olive, M. Positive allosteric modulators of Type 5 metabotropic glutamate receptors (mGlur5) and their therapeutic potential for the treatment of CNS disorders. Molecules 2011, 16, 2097-2106.
    • (2011) Molecules , vol.16 , pp. 2097-2106
    • Cleva R, M.1    Foster Olive, M.2
  • 11
    • 0031045342 scopus 로고    scopus 로고
    • +-ATPase inhibitors. 1. Synthesis and structure-activity relationships of N- substituted 2-(benzhydryl- and benzylsulfinyl)nicotinamides
    • DOI 10.1021/jm9605593
    • +-ATPase inhibitors. 1. Synthesis and structure-activity relationships of N-substituted 2-(benzhydryl- and benzylsulfinyl)nicotinamides. J. Med. Chem. 1997, 40, 313-321. (Pubitemid 27081965)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.3 , pp. 313-321
    • Terauchi, H.1    Tanitame, A.2    Tada, K.3    Nakamura, K.4    Seto, Y.5    Nishikawa, Y.6
  • 13
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide based multicomponent reactions in applied chemistry
    • DOI 10.1021/cr0505728
    • Domling, A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17-89. (Pubitemid 43159621)
    • (2006) Chemical Reviews , vol.106 , Issue.1 , pp. 17-89
    • Domling, A.1
  • 14
    • 70349156384 scopus 로고    scopus 로고
    • Natural product synthesis using multicomponent reaction strategies
    • Toure, B. B.; Hall, D. G Natural product synthesis using multicomponent reaction strategies. Chem. Rev. 2009, 109, 4439-4486.
    • (2009) Chem. Rev , vol.109 , pp. 4439-4486
    • Toure, B.B.1    Hall, D.G.2
  • 15
    • 0033947531 scopus 로고    scopus 로고
    • Multicomponent domino reactions for the synthesis of biologically active natural products and drugs
    • DOI 10.1002/1098-1128(200007)20:4 <304::AID-MED3>3.0.CO;2-8
    • Tietze, L. F.; Modi, A Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med. Res. Rev. 2000, 20, 304-322. (Pubitemid 30430010)
    • (2000) Medicinal Research Reviews , vol.20 , Issue.4 , pp. 304-322
    • Tietze, L.F.1    Modi, A.2
  • 16
    • 0036424932 scopus 로고    scopus 로고
    • The application of multi-component reactions in drug discovery
    • Weber, L. The application of multi-component reactions in drug discovery. Curr. Med. Chem. 2002, 9, 2085-2093. (Pubitemid 35331914)
    • (2002) Current Medicinal Chemistry , vol.9 , Issue.23 , pp. 2085-2093
    • Weber, L.1
  • 17
    • 0037238724 scopus 로고    scopus 로고
    • Multi-component reactions: Emerging chemistry in drug discovery
    • Hulme, C.; Gore, V. Multi-component reactions: Emerging chemistry in drug discovery. Curr. Med. Chem. 2003, 10, 51-80.
    • (2003) Curr. Med. Chem , vol.10 , pp. 51-80
    • Hulme, C.1    Gore, V.2
  • 18
    • 73349126077 scopus 로고    scopus 로고
    • Use ofβ,γ-unsaturated α-ketocarbonyls for a totally regioselective oxidative multicomponent synthesis of polyfunctionalized pyridines
    • Allais, C.; Constantieux, T.; Rodriguez, J. Use ofβ,γ- unsaturated α-ketocarbonyls for a totally regioselective oxidative multicomponent synthesis of polyfunctionalized pyridines. Chem. - Eur. J. 2009, 15, 12945-12948.
    • (2009) Chem. - Eur. J , vol.15 , pp. 12945-12948
    • Allais, C.1    Constantieux, T.2    Rodriguez, J.3
  • 19
    • 79956260862 scopus 로고    scopus 로고
    • New multicomponent cyclization: Domino synthesis of pentasubstituted pyridines under solvent-free conditions
    • Jiang, B.; Wang, X.; Shi, F.; Tu, S. J.; Li, G. New multicomponent cyclization: Domino synthesis of pentasubstituted pyridines under solvent-free conditions. Org. Biomol. Chem. 2011, 9, 4025-4028.
    • (2011) Org. Biomol. Chem , vol.9 , pp. 4025-4028
    • Jiang, B.1    Wang, X.2    Shi, F.3    Tu, S.J.4    Li, G.5
  • 20
    • 34548683910 scopus 로고    scopus 로고
    • Synthesis of nicotinamide and isonicotinamide derivatives via multicomponent reaction of alkyl isocyanides and acetylenic compounds in the presence of nicotinic or isonicotinic acid
    • DOI 10.1055/s-2007-983814
    • Alizadeh, A.; Oskueyan, Q.; Rostamnia, S. Synthesis of nicotinamide and isonicotinamide derivatives via multicomponent reaction of alkyl isocyanides and acetylenic compounds in the presence of nicotinic or isonicotinic acid. Synthesis 2007, 2637-2640. (Pubitemid 47414254)
    • (2007) Synthesis , Issue.17 , pp. 2637-2640
    • Alizadeh, A.1    Oskueyan, Q.2    Rostamnia, S.3
  • 21
    • 79952452030 scopus 로고    scopus 로고
    • Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity
    • Attar, S.; O'Brien, Z.; Alhaddad, H; Golden, M. L.; Calderon-Urrea, A. Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity. Bioorg. Med. Chem. 2011, 19, 2055-2073.
    • (2011) Bioorg. Med. Chem , vol.19 , pp. 2055-2073
    • Attar, S.1    O'Brien, Z.2    Alhaddad, H.3    Golden, M.L.4    Calderon-Urrea, A.5
  • 23
    • 34250795648 scopus 로고    scopus 로고
    • Epoxidation of (E, E)-cinnamylideneacetophenones with hydrogen peroxide and iodosylbenzene with salen-mn(III) as the catalyst
    • Santos, M. M. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Levai, A.; Patonay, T. Epoxidation of (E, E)-cinnamylideneacetophenones with hydrogen peroxide and iodosylbenzene with Salen-Mn(III) as the catalyst. Eur. J. Org. Chem. 2007, 2877-2887.
    • (2007) Eur. J. Org. Chem , pp. 2877-2887
    • Santos, M.M.C.1    Silva, A.M.S.2    Cavaleiro, J.A.S.3    Levai, A.4    Patonay, T.5
  • 24
    • 57349098769 scopus 로고    scopus 로고
    • Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydro-genation
    • Lu, S.-M.; Bolm, C. Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydro-genation. Angew. Chem., Int. Ed. 2008, 47, 8920-8923.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 8920-8923
    • Lu, S.-M.1    Bolm, C.2
  • 25
    • 77749262153 scopus 로고    scopus 로고
    • Mid and high-yielding synthesis of β-keto esters and β-ketoamides
    • Sridharan, V.; Ruiz, M.; Menendez, J. C. Mid and high-yielding synthesis of β-keto esters and β-ketoamides. Synthesis 2010, 1053-1057.
    • (2010) Synthesis , pp. 1053-1057
    • Sridharan, V.1    Ruiz, M.2    Menendez, J.C.3
  • 27
    • 65349107107 scopus 로고    scopus 로고
    • A very efficient cerium(IV) ammonium nitrate-catalyzed, four-component synthesis of tetrahydropyridines and its application to the concise generation of functionalized homoquinolizine frameworks
    • Sridharan, V.; Maiti, S.; Menendez, J. C. A very efficient cerium(IV) ammonium nitrate-catalyzed, four-component synthesis of tetrahydropyridines and its application to the concise generation of functionalized homoquinolizine frameworks. Chem. - Eur. J. 2009, 15, 4565-4572.
    • (2009) Chem. - Eur. J , vol.15 , pp. 4565-4572
    • Sridharan, V.1    Maiti, S.2    Menendez, J.C.3
  • 28
    • 73149118279 scopus 로고    scopus 로고
    • Efficient generation of highly functionalized fused oxazepine frameworks based on a CAN-catalyzed four-component tetrahydropyridine synthesis/ring closing metathesis sequence
    • Sridharan, V.; Maiti, S.; Menendez, J. C. Efficient generation of highly functionalized fused oxazepine frameworks based on a CAN-catalyzed four-component tetrahydropyridine synthesis/ring closing metathesis sequence. J. Org. Chem. 2010, 74, 9365-9371.
    • (2010) J. Org. Chem , vol.74 , pp. 9365-9371
    • Sridharan, V.1    Maiti, S.2    Menendez, J.C.3
  • 29
    • 77956544235 scopus 로고    scopus 로고
    • Synthesis of a library of 5,6-unsubstituted 1,4-dihydropyridines based on a one-pot 4CR/elimination process and their application to the generation of structurally diverse fused nitrogen heterocycles
    • Maiti, S.; Sridharan, V.; Menendez, J. C. Synthesis of a library of 5,6-unsubstituted 1,4-dihydropyridines based on a one-pot 4CR/elimination process and their application to the generation of structurally diverse fused nitrogen heterocycles. J. Comb. Chem. 2010, 12, 713-722.
    • (2010) J. Comb. Chem , vol.12 , pp. 713-722
    • Maiti, S.1    Sridharan, V.2    Menendez, J.C.3
  • 30
    • 68149165476 scopus 로고    scopus 로고
    • Microwave assisted rapid and efficient synthesis of new 3-ethoxy-4,6-diaryl-4,5-dihydro-2,1-benzisoxazole
    • Rajanarendar, E.; Kalyan Rao, E.; Raju, S. Microwave assisted rapid and efficient synthesis of new 3-ethoxy-4,6-diaryl-4,5-dihydro-2,1-benzisoxazole. Indian J. Chem. 2009, 48B, 749.
    • (2009) Indian J. Chem , vol.48 B , pp. 749
    • Rajanarendar, E.1    Kalyan Rao, E.2    Raju, S.3
  • 31
    • 85008077100 scopus 로고
    • Studies on ketene and its derivatives. LXXXI. Reaction of β-aminocrotonamide with α,β-unsaturated ketones
    • Kato, T.; Noda, M. Studies on ketene and its derivatives. LXXXI. Reaction of β-aminocrotonamide with α,β-unsaturated ketones. Chem. Pharm. Bull. 1976, 24, 1408-1410.
    • (1976) Chem. Pharm. Bull , vol.24 , pp. 1408-1410
    • Kato, T.1    Noda, M.2
  • 33
    • 55449109761 scopus 로고    scopus 로고
    • Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction
    • Sridharan, V.; Menendez, J. C. Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction. Org. Lett. 2008, 10, 4303-4306.
    • (2008) Org. Lett , vol.10 , pp. 4303-4306
    • Sridharan, V.1    Menendez, J.C.2
  • 34
    • 34247101798 scopus 로고    scopus 로고
    • General, mild and efficient synthesis of β-enaminones catalyzed by ceric ammonium nitrate
    • DOI 10.1055/s-2007-973862
    • Sridharan, V.; Avendano, C.; Menendez, J. C. General, mild and efficient synthesis of β-enaminones catalyzed by ceric ammonium nitrate. Synlett 2007, 881-884 and 830. (Pubitemid 46596385)
    • (2007) Synlett , Issue.6 , pp. 881-884
    • Sridharan, V.1    Avendano, C.2    Menendez, J.C.3
  • 35
    • 79955480733 scopus 로고    scopus 로고
    • Aza-[3 + 3] annulations: A new unified strategy in alkaloid synthesis
    • Buchanan, GS.; Feltenberger, J. B.; Hsung, R P. Aza-[3 + 3] annulations: A new unified strategy in alkaloid synthesis. Curr. Org. Synth. 2010, 7, 363-401.
    • (2010) Curr. Org. Synth , vol.7 , pp. 363-401
    • Buchanan, G.S.1    Feltenberger, J.B.2    Hsung R, P.3


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