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Volumn 83, Issue , 2014, Pages 466-473

Design and synthesis of 6-oxo-1,4,5,6-tetrahydropyrimidine-5-carboxylate derivatives as neuraminidase inhibitors

Author keywords

6 oxo 1,4,5,6 tetrahydropyrimidine 5 carboxylate derivatives; Anti influenza; Neuraminidase inhibitors; SAR

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ETHYL 2 ACETAMINO 4 (2 CHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (2 NITROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (2,4 DICHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (3,4 DIMETHOXYPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 BROMO 2 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 METHOXYPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 METHYLPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 NITROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 PHENYL 6 OXO 1,4,5, 6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (2 CHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (2 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (2 NITROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (2,4 DICHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIM DINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (3,4 DIMETHOXYPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 (DIMETHYLAMINO) PHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 BROMO 2 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 BROMOPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 CHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 FL UOROPHENYL) 6 OXO 1,4,5, 6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 METHOXYPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 METHYLPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 NITROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (FURAN 2 YL) 6 OXO 1,4,5 6 TETRAHYDROPYRIMIDINE 5 CARBOZYLATE; ETHYL 2 AMINO 4 ISOPROPYL 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 PHENYL 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; 6-OXO-1,4,5,6-TETRAHYDROPYRIMIDINE-5-CARBOXYLATE; ENZYME INHIBITOR; PYRIMIDINE DERIVATIVE; 2 ACETAMINO 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE DERIVATIVE; 2 AMINO 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE DERIVATIVE; ETHYL 2 ACETAMINO 4 (2 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 BROMO 4 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 BROMOPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (4 CHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 (FURAN 2 YL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 ISOPROPYL 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 PHENYL 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 ACETAMINO 4 [4 (DIMETHYLAMINO)PHENYL] 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (2,4 DICHLOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 2 AMINO 4 (4 FLUOROPHENYL) 6 OXO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 (4 BROMOPHENYL) 6 OXO 2 (2,2,2 TRIFLUOROACETAMIDO) 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; ETHYL 4 (4 BROMOPHENYL) 6 OXO 2 PROPIONAMIDO 1,4,5,6 TETRAHYDROPYRIMIDINE 5 CARBOXYLATE; OSELTAMIVIR; VIRUS SIALIDASE;

EID: 84903734164     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.059     Document Type: Article
Times cited : (16)

References (31)
  • 1
    • 41649108175 scopus 로고    scopus 로고
    • Design, synthesis, inhibitory activity, and SAR studies of hydrophobic p-aminosalicylic acid derivatives as neuraminidase inhibitors
    • J. Zhang, Q. Wang, H. Fang, W. Xu, A. Liu, and G. Du Design, synthesis, inhibitory activity, and SAR studies of hydrophobic p-aminosalicylic acid derivatives as neuraminidase inhibitors Bioorg. Med. Chem. 16 2008 3839 3847
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 3839-3847
    • Zhang, J.1    Wang, Q.2    Fang, H.3    Xu, W.4    Liu, A.5    Du, G.6
  • 2
    • 84878110144 scopus 로고    scopus 로고
    • Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors
    • Y. Xie, B. Huang, K. Yu, F. Shi, T. Liu, and W. Xu Caffeic acid derivatives: a new type of influenza neuraminidase inhibitors Bioorg. Med. Chem. Lett. 23 2013 3556 3560
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 3556-3560
    • Xie, Y.1    Huang, B.2    Yu, K.3    Shi, F.4    Liu, T.5    Xu, W.6
  • 3
    • 84883742737 scopus 로고    scopus 로고
    • Design and synthesis of 4-alkyl-2-amino(acetamino)-6-aryl-1,3-thiazine derivatives as influenza neuraminidase inhibitors
    • W. Li, L. Xia, A. Hu, A. Liu, J. Peng, and W. Tan Design and synthesis of 4-alkyl-2-amino(acetamino)-6-aryl-1,3-thiazine derivatives as influenza neuraminidase inhibitors Arch. Pharm. 346 2013 635 644
    • (2013) Arch. Pharm. , vol.346 , pp. 635-644
    • Li, W.1    Xia, L.2    Hu, A.3    Liu, A.4    Peng, J.5    Tan, W.6
  • 5
    • 14844318121 scopus 로고    scopus 로고
    • Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase
    • DOI 10.1016/j.bmc.2005.01.042
    • P. Chand, P.L. Kotian, P.E. Morris, S. Bantia, D.A. Walsh, and Y.S. Babu Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase Bioorg. Med. Chem. 13 2005 2665 2678 (Pubitemid 40341669)
    • (2005) Bioorganic and Medicinal Chemistry , vol.13 , Issue.7 , pp. 2665-2678
    • Chand, P.1    Kotian, P.L.2    Morris, P.E.3    Bantia, S.4    Walsh, D.A.5    Babu, Y.S.6
  • 6
    • 33847636143 scopus 로고    scopus 로고
    • Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors
    • DOI 10.1016/j.bmc.2007.01.020, PII S096808960700034X
    • J. Zhang, Q. Wang, H. Fang, W. Xu, A. Liu, and G. Du Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors Bioorg. Med. Chem. 15 2007 2749 2758 (Pubitemid 46367697)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.7 , pp. 2749-2758
    • Zhang, J.1    Wang, Q.2    Fang, H.3    Xu, W.4    Liu, A.5    Du, G.6
  • 7
    • 0031048319 scopus 로고    scopus 로고
    • Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: Design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity
    • DOI 10.1021/ja963036t, PII S0002786396030363
    • C.U. Kim, W. Lew, M.A. Williams, H.T. Liu, L.J. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, and R.C. Stevens Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity J. Am. Chem. Soc. 119 1997 681 690 (Pubitemid 27101232)
    • (1997) Journal of the American Chemical Society , vol.119 , Issue.4 , pp. 681-690
    • Kim, C.U.1    Lew, W.2    Williams, M.A.3    Liu, H.4    Zhang, L.5    Swaminathan, S.6    Bischofberger, N.7    Chen, M.S.8    Mendel, D.B.9    Tai, C.Y.10    Laver, W.G.11    Stevens, R.C.12
  • 12
    • 18844391810 scopus 로고    scopus 로고
    • Synthesis of screening substrates for the directed evolution of sialic acid aldolase: Towards tailored enzymes for the preparation of influenza a sialidase inhibitor analogues
    • DOI 10.1039/b501503k
    • T. Woodhall, G. Williams, A. Berry, and A. Nelson Synthesis of screening substrates for the directed evolution of sialic acid aldolase: towards tailored enzymes for the preparation of influenza A sialidase inhibitor analogues Org. Biomol. Chem. 3 2005 1795 1800 (Pubitemid 40683108)
    • (2005) Organic and Biomolecular Chemistry , vol.3 , Issue.9 , pp. 1795-1800
    • Woodhall, T.1    Williams, G.2    Berry, A.3    Nelson, A.4
  • 17
    • 18444369293 scopus 로고    scopus 로고
    • A new class of potent nonpeptide luteinizing hormone-releasing hormone (LHRH) antagonists: Design and synthesis of 2-phenylimidazo[1,2-a]pyrimidin-5- ones
    • DOI 10.1016/S0960-894X(02)00372-4, PII S0960894X02003724
    • S. Sasaki, T. Imaeda, Y. Hayase, Y. Shimizu, S. Kasai, N. Cho, M. Harada, N. Suzuki, S. Furuya, and M. Fujino A new class of potent nonpeptide luteinizing hormone-releasing hormone (LHRH) antagonists: design and synthesis of 2-phenylimidazo[1,2-a]pyrimidin-5-ones Bioorg. Med. Chem. Lett. 12 2002 2073 2077 (Pubitemid 34804369)
    • (2002) Bioorganic and Medicinal Chemistry Letters , vol.12 , Issue.16 , pp. 2073-2077
    • Sasaki, S.1    Imaeda, T.2    Hayase, Y.3    Shimizu, Y.4    Kasai, S.5    Cho, N.6    Harada, M.7    Suzuki, N.8    Furuya, S.9    Fujino, M.10
  • 20
    • 33748437791 scopus 로고    scopus 로고
    • The structure of H5N1 avian influenza neuraminidase suggests new opportunities for drug design
    • DOI 10.1038/nature05114, PII NATURE05114
    • R.J. Russell, L.F. Haire, D.J. Stevens, P.J. Collins, Y.P. Lin, G.M. Blackburn, A.J. Hay, S.J. Gamblin, and J.J. Skehel The structure of H5N1 avian influenza neuraminidase suggests new opportunities for drug design Nature 443 2006 45 49 (Pubitemid 44344043)
    • (2006) Nature , vol.443 , Issue.7107 , pp. 45-49
    • Russell, R.J.1    Haire, L.F.2    Stevens, D.J.3    Collins, P.J.4    Lin, Y.P.5    Blackburn, G.M.6    Hay, A.J.7    Gamblin, S.J.8    Skehel, J.J.9
  • 23
    • 0021177989 scopus 로고
    • Influenza virus neuraminidase with hemagglutinin activity
    • DOI 10.1016/0042-6822(84)90223-X
    • W.G. Laver, P.M. Colman, R.G. Webster, V.S. Hinshaw, and G.M. Air Influenza virus neuraminidase with hemagglutinin activity Virology 137 1984 314 323 (Pubitemid 14000576)
    • (1984) Virology , vol.137 , Issue.2 , pp. 314-323
    • Laver, W.G.1    Colman, P.M.2    Webster, R.G.3
  • 25
    • 27144449695 scopus 로고    scopus 로고
    • Designed multiple ligands. An emerging drug discovery paradigm
    • DOI 10.1021/jm058225d
    • R. Morphy, and Z. Rankovic Designed multiple ligands. An emerging drug discovery paradigm J. Med. Chem. 48 2005 6523 6543 (Pubitemid 41504710)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.21 , pp. 6523-6543
    • Morphy, R.1    Rankovic, Z.2
  • 26
    • 79956158018 scopus 로고    scopus 로고
    • Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates
    • T. Wang, J. Liu, H. Zhong, H. Chen, Z. Lv, Y. Zhang, M. Zhang, D. Geng, C. Niu, Y. Li, and K. Li Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates Bioorg. Med. Chem. Lett. 21 2011 3381 3383
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 3381-3383
    • Wang, T.1    Liu, J.2    Zhong, H.3    Chen, H.4    Lv, Z.5    Zhang, Y.6    Zhang, M.7    Geng, D.8    Niu, C.9    Li, Y.10    Li, K.11
  • 27
    • 36748999350 scopus 로고    scopus 로고
    • Catalyzed Knoevenagel reactions on inorganic solid sorts: Application to the synthesis of coumarine compounds
    • Y. Moussaoui, and R. Ben Salem Catalyzed Knoevenagel reactions on inorganic solid sorts: application to the synthesis of coumarine compounds C. R. Chim. 10 2007 1162 1169
    • (2007) C. R. Chim. , vol.10 , pp. 1162-1169
    • Moussaoui, Y.1    Ben Salem, R.2
  • 28
    • 0038739702 scopus 로고
    • Synthesis of novel 5-alkoxycarbonyl-5,6-dihydropyrimidin -4(3H)-ones from 3-substituted-2′-alkoxycarbonyl-2-propenoates and amidines
    • H. Cho, M. Veda, Y. Ohnaka, and M. Hayashimatsu Synthesis of novel 5-alkoxycarbonyl-5,6-dihydropyrimidin -4(3H)-ones from 3-substituted-2′- alkoxycarbonyl-2-propenoates and amidines Heterocycles 22 1984 1959 1963
    • (1984) Heterocycles , vol.22 , pp. 1959-1963
    • Cho, H.1    Veda, M.2    Ohnaka, Y.3    Hayashimatsu, M.4
  • 29
    • 1842604435 scopus 로고
    • Acetylation of some aminopyrimidines
    • A.P. Phillips, and J. Mentha Acetylation of some aminopyrimidines J. Am. Chem. Soc. 76 1954 6200 6202
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 6200-6202
    • Phillips, A.P.1    Mentha, J.2
  • 30
    • 65449190174 scopus 로고    scopus 로고
    • An improved synthesis of Biginelli-type compounds via phase-transfer catalysis
    • B. Ahmed, R.A. Khan, Habibullah, and M. Keshari An improved synthesis of Biginelli-type compounds via phase-transfer catalysis Tetrahedron Lett. 50 2009 2889 2892
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2889-2892
    • Ahmed, B.1    Khan, R.A.2    Habibullah3    Keshari, M.4
  • 31
    • 0018216717 scopus 로고
    • Pyrimidine derivatives and related compounds. 31. A new photochemical transformation of 6-azido-1,3-dimethyluracil to 6-alkylamino-5-amino-1,3- dimethyluracils and its application to one-step synthesis of lumazines and fervenulins
    • S. Senda, K. Hirota, T. Asao, and K. Maruhashi Pyrimidine derivatives and related compounds. 31. A new photochemical transformation of 6-azido-1,3-dimethyluracil to 6-alkylamino-5-amino-1,3-dimethyluracils and its application to one-step synthesis of lumazines and fervenulins J. Am. Chem. Soc. 100 1978 7661 7664 (Pubitemid 9101137)
    • (1978) Journal of the American Chemical Society , vol.100 , Issue.24 , pp. 7661-7664
    • Senda, S.1    Hirota, K.2    Asao, T.3    Maruhashi, K.4


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