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Volumn 16, Issue 8, 2014, Pages 403-411

Ugi-based approaches to quinoxaline libraries

Author keywords

operationally simple synthesis; quinoxaline libraries; Ugi based approach

Indexed keywords

MOLECULAR LIBRARY; QUINOXALINE DERIVATIVE;

EID: 84905828977     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co500036n     Document Type: Article
Times cited : (23)

References (58)
  • 3
    • 15444370985 scopus 로고    scopus 로고
    • Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti- Mycobacterium tuberculosis agents
    • Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti- Mycobacterium tuberculosis agents J. Med. Chem. 2005, 48, 2019-2025
    • (2005) J. Med. Chem. , vol.48 , pp. 2019-2025
    • Jaso, A.1    Zarranz, B.2    Aldana, I.3    Monge, A.4
  • 5
    • 0037028002 scopus 로고    scopus 로고
    • Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives
    • Seitz, L. E.; Suling, W. J.; Reynolds, R. C. Synthesis and antimycobacterial activity of pyrazine and quinoxaline derivatives J. Med. Chem. 2002, 45, 5604-5606
    • (2002) J. Med. Chem. , vol.45 , pp. 5604-5606
    • Seitz, L.E.1    Suling, W.J.2    Reynolds, R.C.3
  • 6
    • 0038102249 scopus 로고    scopus 로고
    • DNA sequence specificity for topoisomerase II poisoning by the quinoxaline anticancer drugs XK469 and CQS
    • Gao, H.; Yamasaki, E. F.; Chan, K. K.; Shen, L. L.; Snapka, R. M. DNA sequence specificity for topoisomerase II poisoning by the quinoxaline anticancer drugs XK469 and CQS Mol. Pharmacol. 2003, 63, 1382-1388
    • (2003) Mol. Pharmacol. , vol.63 , pp. 1382-1388
    • Gao, H.1    Yamasaki, E.F.2    Chan, K.K.3    Shen, L.L.4    Snapka, R.M.5
  • 7
    • 0017101648 scopus 로고
    • Chemistry and toxicology of quinoxaline, organotin, organofluorine, and formamidine acaricides
    • Knowles, C. O. Chemistry and toxicology of quinoxaline, organotin, organofluorine, and formamidine acaricides Environ. Health Perspect. 1976, 14, 93-102
    • (1976) Environ. Health Perspect. , vol.14 , pp. 93-102
    • Knowles, C.O.1
  • 8
    • 0344300655 scopus 로고
    • Aryl-substituted quinoxalines and related heteroarenes as novel herbicides prepared via palladium-catalyzed cross-coupling methods
    • Selby, T. P.; Denes, L. R.; Kilama, J. L.; Smith, B. K. Aryl-substituted quinoxalines and related heteroarenes as novel herbicides prepared via palladium-catalyzed cross-coupling methods ACS Symp. Ser. 1995, 584, 171-185
    • (1995) ACS Symp. Ser. , vol.584 , pp. 171-185
    • Selby, T.P.1    Denes, L.R.2    Kilama, J.L.3    Smith, B.K.4
  • 9
    • 45549120599 scopus 로고
    • Recent Progress in the quinoline chemistry. Synthesis and biological activity
    • Sakata, G.; Makino, K.; Kurasawa, Y. Recent Progress in the quinoline chemistry. Synthesis and biological activity Heterocycles 1988, 27, 2481-2515
    • (1988) Heterocycles , vol.27 , pp. 2481-2515
    • Sakata, G.1    Makino, K.2    Kurasawa, Y.3
  • 11
    • 0014149126 scopus 로고
    • Chemical studies on riboflavin and related compounds. I. Oxidation of quinoxaline-2,3-diols as a possible model for the biological decomposition of riboflavin
    • Saito, I.; Matsuura, T. Chemical studies on riboflavin and related compounds. I. Oxidation of quinoxaline-2,3-diols as a possible model for the biological decomposition of riboflavin Biochemistry 1967, 6, 3602-3608
    • (1967) Biochemistry , vol.6 , pp. 3602-3608
    • Saito, I.1    Matsuura, T.2
  • 12
    • 78549232975 scopus 로고    scopus 로고
    • Two new amide alkaloids from the flower of Datura metel L
    • Yan, B. Y.; Xia, Y. G.; Wang, Q. H.; Dou, D. Q.; Kuang, H. X. Two new amide alkaloids from the flower of Datura metel L Fitoterapia 2010, 81, 1003-1005
    • (2010) Fitoterapia , vol.81 , pp. 1003-1005
    • Yan, B.Y.1    Xia, Y.G.2    Wang, Q.H.3    Dou, D.Q.4    Kuang, H.X.5
  • 13
    • 0016315511 scopus 로고
    • Actinomycin. Chemistry and mechanism of action
    • Hollstein, U. Actinomycin. Chemistry and mechanism of action Chem. Rev. 1974, 74, 625-652
    • (1974) Chem. Rev. , vol.74 , pp. 625-652
    • Hollstein, U.1
  • 15
    • 77952477596 scopus 로고    scopus 로고
    • Privileged scaffolds for library design and drug discovery
    • Welsch, M. E.; Snyder, S. A.; Strockwell, B. R. Privileged scaffolds for library design and drug discovery Curr. Op. Chem. Biol. 2010, 14, 347-361
    • (2010) Curr. Op. Chem. Biol. , vol.14 , pp. 347-361
    • Welsch, M.E.1    Snyder, S.A.2    Strockwell, B.R.3
  • 16
    • 33644872086 scopus 로고    scopus 로고
    • Privileged structures as leads in medicinal chemistry
    • Constantino, L.; Barolocco, D. Privileged structures as leads in medicinal chemistry Curr. Med. Chem. 2006, 13, 65-85
    • (2006) Curr. Med. Chem. , vol.13 , pp. 65-85
    • Constantino, L.1    Barolocco, D.2
  • 17
    • 18144408330 scopus 로고    scopus 로고
    • Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials
    • Thomas, K. R. J.; Marappan, V.; Jian, T. L.; Chang-Hao, C.; Yu-ai, T. Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials Chem. Mater. 2005, 17, 1860-1866
    • (2005) Chem. Mater. , vol.17 , pp. 1860-1866
    • Thomas, K.R.J.1    Marappan, V.2    Jian, T.L.3    Chang-Hao, C.4    Yu-Ai, T.5
  • 18
    • 0034842923 scopus 로고    scopus 로고
    • Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications
    • Dailey, S.; Feast, J. W.; Peace, R. J.; Saga, R. C.; Till, S.; Wood, E. L. Synthesis and device characterisation of side-chain polymer electron transport materials for organic semiconductor applications J. Mater. Chem. 2001, 11, 2238-2243
    • (2001) J. Mater. Chem. , vol.11 , pp. 2238-2243
    • Dailey, S.1    Feast, J.W.2    Peace, R.J.3    Saga, R.C.4    Till, S.5    Wood, E.L.6
  • 19
    • 0037034055 scopus 로고    scopus 로고
    • Molecular design and evaluation of quinoxaline-carbohydrate hybrids as novel and efficient photo-induced GG-selective DNA cleaving agents
    • Toshima, K.; Takano, R.; Ozawa, T.; Matsumura, S. Molecular design and evaluation of quinoxaline-carbohydrate hybrids as novel and efficient photo-induced GG-selective DNA cleaving agents Chem. Commun. 2002, 212-213
    • (2002) Chem. Commun. , pp. 212-213
    • Toshima, K.1    Takano, R.2    Ozawa, T.3    Matsumura, S.4
  • 20
    • 15344346264 scopus 로고    scopus 로고
    • Metal-assisted red light-induced DNA cleavage by ternary l -methionine copper(II) complexes of planar heterocyclic bases
    • Patra, A. K.; Dhar, S.; Nethaji, M.; Chakravarty, A. R. Metal-assisted red light-induced DNA cleavage by ternary l -methionine copper(II) complexes of planar heterocyclic bases Dalton Trans. 2005, 896-902
    • (2005) Dalton Trans. , pp. 896-902
    • Patra, A.K.1    Dhar, S.2    Nethaji, M.3    Chakravarty, A.R.4
  • 21
    • 0036095908 scopus 로고    scopus 로고
    • Synthesis and reactions of 2-amino-6-(3-methyl-5-oxo-1-phenyl-2- pyrazolin-4-yl)-4-phenylpyridine-3-carbonitrile
    • Sonawane, N. D.; Rangnekar, D. W. Synthesis and reactions of 2-amino-6-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-4-phenylpyridine-3- carbonitrile J. Heterocycl. Chem. 2002, 39, 303-308
    • (2002) J. Heterocycl. Chem. , vol.39 , pp. 303-308
    • Sonawane, N.D.1    Rangnekar, D.W.2
  • 22
    • 84944048121 scopus 로고
    • Katritzky, A. R. Rees, C. W. Pergamon: Oxford, U.K
    • Porter, A. E. A. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; pp 157-197.
    • (1984) Comprehensive Heterocyclic Chemistry , pp. 157-197
    • Porter, A.E.A.1
  • 23
    • 2942546340 scopus 로고    scopus 로고
    • Chapter 6.2-Six-membered ring systems: Diazines and benzo derivatives
    • Woo, G. H.; Snyder, J. K.; Wan, Z. K. Chapter 6.2-Six-membered ring systems: Diazines and benzo derivatives Prog. Heterocycl. Chem. 2002, 14, 279-309
    • (2002) Prog. Heterocycl. Chem. , vol.14 , pp. 279-309
    • Woo, G.H.1    Snyder, J.K.2    Wan, Z.K.3
  • 24
    • 84866496620 scopus 로고    scopus 로고
    • Chapter 2-Progress in quinoxaline synthesis (Part 1)
    • Mamedov, V. A.; Zhukova, N. A. Chapter 2-Progress in quinoxaline synthesis (Part 1) Prog. Heterocycl. Chem. 2012, 24, 55-88
    • (2012) Prog. Heterocycl. Chem. , vol.24 , pp. 55-88
    • Mamedov, V.A.1    Zhukova, N.A.2
  • 25
    • 84883545226 scopus 로고    scopus 로고
    • Chapter 1-Progress in quinoxaline synthesis (Part 2)
    • Mamedov, V. A.; Zhukova, N. A. Chapter 1-Progress in quinoxaline synthesis (Part 2) Prog. Heterocycl. Chem. 2013, 25, 1-45
    • (2013) Prog. Heterocycl. Chem. , vol.25 , pp. 1-45
    • Mamedov, V.A.1    Zhukova, N.A.2
  • 29
    • 78149305896 scopus 로고    scopus 로고
    • Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009
    • Dolle, R. E.; Le Bourdonnec, B.; Worm, K.; Morales, G. A.; Thomas, C. J.; Zhang, W. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009 J. Comb. Chem. 2010, 12, 765-806
    • (2010) J. Comb. Chem. , vol.12 , pp. 765-806
    • Dolle, R.E.1    Le Bourdonnec, B.2    Worm, K.3    Morales, G.A.4    Thomas, C.J.5    Zhang, W.6
  • 30
    • 33845537355 scopus 로고    scopus 로고
    • Quinoxalines
    • Taylor, E. C. Wipf, P. John Wiley & Sons: Hoboken, NJ
    • Brown, D. J. Quinoxalines. In The Chemistry of Heterocyclic Compounds; Taylor, E. C.; Wipf, P., Eds.; John Wiley & Sons: Hoboken, NJ, 2004; pp 1-510.
    • (2004) The Chemistry of Heterocyclic Compounds , pp. 1-510
    • Brown, D.J.1
  • 32
    • 77958518749 scopus 로고    scopus 로고
    • New and modified classical methods for the synthesis of quinoxalines
    • Saifina, D. F.; Mamedov, V. A. New and modified classical methods for the synthesis of quinoxalines Russ. Chem. Rev. 2010, 79, 351-370
    • (2010) Russ. Chem. Rev. , vol.79 , pp. 351-370
    • Saifina, D.F.1    Mamedov, V.A.2
  • 33
    • 0000642104 scopus 로고
    • Application of benzofurazan oxide to the synthesis of heteroaromatic N -oxides
    • Haddadin, M. J.; Issidorides, C. H. Application of benzofurazan oxide to the synthesis of heteroaromatic N -oxides Heterocycles 1976, 4, 767-816
    • (1976) Heterocycles , vol.4 , pp. 767-816
    • Haddadin, M.J.1    Issidorides, C.H.2
  • 34
    • 0002202106 scopus 로고
    • Enamines with isobenzofuroxan: A novel synthesis of quinoxaline-di- n -oxides
    • Haddadin, M. J.; Issidorides, C. H. Enamines with isobenzofuroxan: a novel synthesis of quinoxaline-di- n -oxides Tetrahedron Lett. 1965, 6, 3253-3256
    • (1965) Tetrahedron Lett. , vol.6 , pp. 3253-3256
    • Haddadin, M.J.1    Issidorides, C.H.2
  • 35
    • 33947336447 scopus 로고
    • Benzofurazan oxide. II. Reactions with enolate anions
    • Issidorides, C. H.; Haddadin, M. J. Benzofurazan oxide. II. Reactions with enolate anions J. Org. Chem. 1966, 31, 4067-4068
    • (1966) J. Org. Chem. , vol.31 , pp. 4067-4068
    • Issidorides, C.H.1    Haddadin, M.J.2
  • 37
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide based multicomponent reactions in applied chemistry
    • Dömling, A. Recent developments in isocyanide based multicomponent reactions in applied chemistry Chem. Rev. 2006, 106, 17-89
    • (2006) Chem. Rev. , vol.106 , pp. 17-89
    • Dömling, A.1
  • 38
    • 0000512227 scopus 로고    scopus 로고
    • Multiple-component condensation strategies for combinatorial library synthesis
    • Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Multiple-component condensation strategies for combinatorial library synthesis Acc. Chem. Res. 1996, 29, 123-131
    • (1996) Acc. Chem. Res. , vol.29 , pp. 123-131
    • Armstrong, R.W.1    Combs, A.P.2    Tempest, P.A.3    Brown, S.D.4    Keating, T.A.5
  • 40
    • 33646036709 scopus 로고    scopus 로고
    • Highly substituted indol-2-ones, quinoxalin-2-ones, and benzodiazepin-2,5-diones via a new Ugi(4CR)-Pd assisted N -aryl amidation strategy
    • Kalinski, C.; Umkehrer, M.; Ross, G.; Kolb, J.; Burdack, C.; Hiller, W. Highly substituted indol-2-ones, quinoxalin-2-ones, and benzodiazepin-2,5-diones via a new Ugi(4CR)-Pd assisted N -aryl amidation strategy Tetrahedron Lett. 2006, 47, 3423-3426
    • (2006) Tetrahedron Lett. , vol.47 , pp. 3423-3426
    • Kalinski, C.1    Umkehrer, M.2    Ross, G.3    Kolb, J.4    Burdack, C.5    Hiller, W.6
  • 41
    • 45149102410 scopus 로고    scopus 로고
    • Ugi-Smiles access to quinoxaline derivatives
    • Oble, J.; El Kaim, L.; Gizzi, M.; Grimaud, L. Ugi-Smiles access to quinoxaline derivatives Heterocycles 2007, 73, 503-517
    • (2007) Heterocycles , vol.73 , pp. 503-517
    • Oble, J.1    El Kaim, L.2    Gizzi, M.3    Grimaud, L.4
  • 42
    • 84866356856 scopus 로고    scopus 로고
    • A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families
    • De Moliner, F.; Hulme, C. A Van Leusen deprotection-cyclization strategy as a fast entry into two imidazoquinoxaline families Tetrahedron Lett. 2012, 53, 5787-5790
    • (2012) Tetrahedron Lett. , vol.53 , pp. 5787-5790
    • De Moliner, F.1    Hulme, C.2
  • 43
    • 84857367291 scopus 로고    scopus 로고
    • Concise route to a series of novel 3-(tetrazol-5-yl)quinoxalin-2(1 H)-ones
    • Gunawan, S.; Nichol, G.; Hulme, C. Concise route to a series of novel 3-(tetrazol-5-yl)quinoxalin-2(1 H)-ones Tetrahedron Lett. 2012, 53, 1664-1667
    • (2012) Tetrahedron Lett. , vol.53 , pp. 1664-1667
    • Gunawan, S.1    Nichol, G.2    Hulme, C.3
  • 44
    • 41349097979 scopus 로고    scopus 로고
    • Expedient entry into 1,4-dihydroquinoxalines and quinoxalines via a novel variant of isocyanide-based MCR
    • Krasavin, M.; Parchinsky, V. Expedient entry into 1,4-dihydroquinoxalines and quinoxalines via a novel variant of isocyanide-based MCR Synlett 2008, 645-648
    • (2008) Synlett , pp. 645-648
    • Krasavin, M.1    Parchinsky, V.2
  • 45
    • 64149097753 scopus 로고    scopus 로고
    • Imidazo[1,2- a ]quinoxalines accessed via two sequential isocyanide-based multicomponent reactions
    • Krasavin, M.; Shkavrov, S.; Parchinsky, V.; Bukhryakov, K. Imidazo[1,2- a ]quinoxalines accessed via two sequential isocyanide-based multicomponent reactions J. Org. Chem. 2009, 74, 2627-2629
    • (2009) J. Org. Chem. , vol.74 , pp. 2627-2629
    • Krasavin, M.1    Shkavrov, S.2    Parchinsky, V.3    Bukhryakov, K.4
  • 46
    • 58149093267 scopus 로고    scopus 로고
    • A novel three-component reaction for the synthesis of N -cyclohexyl-3-aryl-quinoxaline-2-amines
    • Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. A novel three-component reaction for the synthesis of N -cyclohexyl-3-aryl-quinoxaline-2-amines Tetrahedron Lett. 2009, 50, 767-769
    • (2009) Tetrahedron Lett. , vol.50 , pp. 767-769
    • Heravi, M.M.1    Baghernejad, B.2    Oskooie, H.A.3
  • 47
    • 84995181383 scopus 로고
    • The -addition of immonium ions and anions to isonitriles accompanied by secondary reactions
    • Ugi, I. The -addition of immonium ions and anions to isonitriles accompanied by secondary reactions Angew. Chem., Int. Ed. Engl. 1962, 1, 8-20
    • (1962) Angew. Chem., Int. Ed. Engl. , vol.1 , pp. 8-20
    • Ugi, I.1
  • 49
    • 0037391570 scopus 로고    scopus 로고
    • Recent developments in the isonitrile-based multicomponent synthesis of heterocycles
    • Zhu, J. Recent developments in the isonitrile-based multicomponent synthesis of heterocycles Eur. J. Org. Chem. 2003, 1133-1144
    • (2003) Eur. J. Org. Chem. , pp. 1133-1144
    • Zhu, J.1
  • 50
    • 27844439456 scopus 로고    scopus 로고
    • Recent advances in heterocycles generation using the efficient Ugi multiple-component condensation reaction
    • Tempest, P. A. Recent advances in heterocycles generation using the efficient Ugi multiple-component condensation reaction Curr. Opin. Drug Discovery Dev. 2005, 8, 776-788
    • (2005) Curr. Opin. Drug Discovery Dev. , vol.8 , pp. 776-788
    • Tempest, P.A.1
  • 51
    • 60749120878 scopus 로고    scopus 로고
    • Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds
    • Sunderhaus, J. D.; Martin, S. F. Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds Chem.-Eur. J. 2009, 15, 1300-1308
    • (2009) Chem.-Eur. J. , vol.15 , pp. 1300-1308
    • Sunderhaus, J.D.1    Martin, S.F.2
  • 52
    • 0032578740 scopus 로고    scopus 로고
    • Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy
    • Hulme, C.; Peng, J.; Louridas, B.; Menard, P.; Krolikowski, P.; Kumar, N. V. Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy Tetrahedron Lett. 1998, 39, 8047-8050
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8047-8050
    • Hulme, C.1    Peng, J.2    Louridas, B.3    Menard, P.4    Krolikowski, P.5    Kumar, N.V.6
  • 53
    • 84865018544 scopus 로고    scopus 로고
    • General one-pot, two-step protocol accessing a range of novel polycyclic heterocycles with high skeletal diversity
    • Xu, Z.; Ayaz, M.; Cappeli, A. A.; Hulme, C. General one-pot, two-step protocol accessing a range of novel polycyclic heterocycles with high skeletal diversity ACS Comb. Sci. 2012, 14, 460-464
    • (2012) ACS Comb. Sci. , vol.14 , pp. 460-464
    • Xu, Z.1    Ayaz, M.2    Cappeli, A.A.3    Hulme, C.4
  • 54
    • 70449378714 scopus 로고    scopus 로고
    • Microwave-assisted fluorous synthesis of a 1,4-benzodiazepine-2,5-dione library
    • Liu, A.; Zhou, H.; Su, G.; Zhang, W.; Yan, B. Microwave-assisted fluorous synthesis of a 1,4-benzodiazepine-2,5-dione library J. Comb. Chem. 2009, 11, 1083-1093
    • (2009) J. Comb. Chem. , vol.11 , pp. 1083-1093
    • Liu, A.1    Zhou, H.2    Su, G.3    Zhang, W.4    Yan, B.5
  • 55
    • 77955710385 scopus 로고    scopus 로고
    • Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines
    • Xu, Z.; Dietrich, J.; Shaw, A. Y.; Hulme, C. Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines Tetrahedron Lett. 2010, 51, 4566-4569
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4566-4569
    • Xu, Z.1    Dietrich, J.2    Shaw, A.Y.3    Hulme, C.4
  • 56
    • 17744403755 scopus 로고    scopus 로고
    • N -Acylazinium salts: A new source of iminium ions for Ugi-type processes
    • Díaz, J. L.; Miguel, M.; Lavilla, R. N -Acylazinium salts: A new source of iminium ions for Ugi-type processes J. Org. Chem. 2004, 69, 3550-3553
    • (2004) J. Org. Chem. , vol.69 , pp. 3550-3553
    • Díaz, J.L.1    Miguel, M.2    Lavilla, R.3
  • 57
    • 50849087128 scopus 로고    scopus 로고
    • Catalytic three-component Ugi reaction
    • Pan, S. C.; List, B. Catalytic three-component Ugi reaction Angew. Chem., Int. Ed. 2008, 47, 3622-3625
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3622-3625
    • Pan, S.C.1    List, B.2


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