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Volumn 5, Issue 3, 2014, Pages 225-242

Synthesis, biological evaluation, and computational studies of Tri- and tetracyclic nitrogen-bridgehead compounds as potent dual-acting AChE inhibitors and h H3 receptor antagonists

Author keywords

Acetylcholinesterase inhibitors; Alzheimer's disease; docking; MD simulation

Indexed keywords

10 (3 BROMOPROPOXY) 13 METHYL 13,13A DIHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLIN 8(6H) ONE; 10 (BENZYLOXY) 13 METHYL 13,13A DIHYDRO 5H ISOQUINOLINO[1,2B]QUINAZOLIN 8(6H) ONE; 10 HYDROXY 13 METHYL 13,13A DIHYDRO 5H ISOQUINOLINO [1,2 B]QUINAZOLIN 8(6H) ONE; 10 [(6 BROMOHEXYL)OXY] 13 METHYL 13,13A DIHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLIN 8(6H) ONE; 10 [3 (AZEPAN 1 YL)PROPOXY] 13 METHYL 13,13A DIHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLIN 8(6H) ONE; 10 [3 (AZEPAN 1 YL)PROPOXY] 13 METHYL 6,8,13,13A TETRAHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLINE; 13 METHYL 10 (3 MORPHOLINOPROPOXY) 13,13A DIHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLIN 8(6H) ONE; 13 METHYL 10 [3 (PIPERIDIN 1 YL)PROPOXY] 13,13A DIHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLIN 8(6H) ONE; 13 METHYL 10 [3 (PIPERIDIN 1 YL)PROPOXY] 6,8,13,13A TETRAHYDRO13 METHYL 10 TETRAHYDRO 5H ISOQUINAZOLINO[1,2 B]QUINAZOLINE; 13 METHYL 10 [3 (PYRROLIDIN 1 YL)PROPOXY] 13,13A DIHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLIN 8(6H) ONE; 13 METHYL 10 [3 (PYRROLIDIN 1 YL)PROPOXY] 6,8,13,13A TETRAHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLINE; 13 METHYL 10 [[6 (PIPERIDIN 1 YL)HEXYL]OXY] 6,8,13,13A TETRAHYDRO 5H ISOQUINOLINO[1,2 B]QUINAZOLINE; 4 [3 [(13 METHYL 6,8,13,13A TETRAHYDRO 5H ISOQUINOLINO [1,2 B]QUINAZOLIN 10YL)OXY]PROPYL]MORPHOLINE; 6 AMINO 3 BENZYLOXY N ETHOXYCARBONYLBENZOIC ACID; 6 BENZYLOXYISATOIC ANHYDRIDE; 7 (3 BROMOPROPOXY) 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; 7 (BENZYLOXY) 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; 7 HYDROXY 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; 7 [3 (AZEPAN 1 YL)PROPOXY] 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; 7 [3 (PIPERIDIN 1 YL)PROPOXY] 1,2,3,3A,4,9 HEXAHYDROPYRROLO[2,1 B]QUINAZOLINE; 7 [3 (PIPERIDIN 1 YL)PROPOXY] 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; 7 [3 (PYRROLIDIN 1 YL)PROPOXY] 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; 7 [[6 (PIPERIDIN 1 YL)HEXYL]OXY] 1,2,3,9 TETRAHYDROPYRROLO[2,1 B]QUINAZOLINE; 7 [[6 (PIPERIDIN 1 YL)HEXYL]OXY] 2,3 DIHYDROPYRROLO[2,1 B]QUINAZOLIN 9(1H) ONE; ACETYLCHOLINE; CHOLINESTERASE INHIBITOR; HISTAMINE H3 RECEPTOR ANTAGONIST; NITROGEN DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ACETYLCHOLINESTERASE; GUANOSINE TRIPHOSPHATASE; HISTAMINE H1 RECEPTOR; HISTAMINE H2 RECEPTOR; HISTAMINE H3 RECEPTOR; HISTAMINE RECEPTOR;

EID: 84896446908     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn4002126     Document Type: Article
Times cited : (73)

References (60)
  • 1
    • 77949336151 scopus 로고    scopus 로고
    • 2010 Alzheimer's disease facts and figures
    • Maslow, K. (2010) 2010 Alzheimer's disease facts and figures Alzheimer's Dementia 6, 158-194
    • (2010) Alzheimer's Dementia , vol.6 , pp. 158-194
    • Maslow, K.1
  • 3
  • 5
    • 0011162190 scopus 로고
    • Selective loss of central cholinergic neurons in Alzheimer's disease
    • Davies, P. and Maloney, A. J. F. (1976) Selective loss of central cholinergic neurons in Alzheimer's disease Lancet 308, 1403
    • (1976) Lancet , vol.308 , pp. 1403
    • Davies, P.1    Maloney, A.J.F.2
  • 9
    • 33645287272 scopus 로고    scopus 로고
    • 3 receptor antagonists: Preclinical promise for treating obesity and cognitive disorders
    • 3 receptor antagonists: preclinical promise for treating obesity and cognitive disorders Mol. Interventions 6, 77-88
    • (2006) Mol. Interventions , vol.6 , pp. 77-88
    • Esbenshade, T.A.1    Fox, G.B.2    Cowart, M.D.3
  • 10
    • 84875015118 scopus 로고    scopus 로고
    • 3 Receptor Function and Ligands: Recent Developments
    • 3 Receptor Function and Ligands: Recent Developments Mini-Rev. Med. Chem. 13, 47-57
    • (2013) Mini-Rev. Med. Chem. , vol.13 , pp. 47-57
    • Singh, M.1    Jadhav, H.R.2
  • 14
    • 84862279415 scopus 로고    scopus 로고
    • Tacrine-Silibinin codrug shows neuro- and hepatoprotective effects in vitro and pro-cognitive and hepatoprotective effects in vivo
    • Chen, X., Zenger, K., Lupp, A., Kling, B., Heilmann, J., Fleck, C., Kraus, B., and Decker, M. (2012) Tacrine-Silibinin codrug shows neuro- and hepatoprotective effects in vitro and pro-cognitive and hepatoprotective effects in vivo J. Med. Chem. 55, 5231-5242
    • (2012) J. Med. Chem. , vol.55 , pp. 5231-5242
    • Chen, X.1    Zenger, K.2    Lupp, A.3    Kling, B.4    Heilmann, J.5    Fleck, C.6    Kraus, B.7    Decker, M.8
  • 15
    • 84877982789 scopus 로고    scopus 로고
    • Multi-target compounds acting in the central nervous system designed from natural products
    • Chen, X. and Decker, M. (2013) Multi-target compounds acting in the central nervous system designed from natural products Curr. Med. Chem. 20, 1673-1685
    • (2013) Curr. Med. Chem. , vol.20 , pp. 1673-1685
    • Chen, X.1    Decker, M.2
  • 16
    • 33947683747 scopus 로고    scopus 로고
    • Recent advances in the development of hybrid molecules/designed multiple compounds with antiamnesic properties
    • Decker, M. (2007) Recent advances in the development of hybrid molecules/designed multiple compounds with antiamnesic properties Mini-Rev. Med. Chem. 7, 221-229
    • (2007) Mini-Rev. Med. Chem. , vol.7 , pp. 221-229
    • Decker, M.1
  • 17
    • 80054848108 scopus 로고    scopus 로고
    • Multi-target-directed ligands in Alzheimer's disease treatment
    • Bajda, M., Guzior, N., Ignasik, M., and Malawska, B. (2011) Multi-target-directed ligands in Alzheimer's disease treatment Curr. Med. Chem. 18, 4949-4975
    • (2011) Curr. Med. Chem. , vol.18 , pp. 4949-4975
    • Bajda, M.1    Guzior, N.2    Ignasik, M.3    Malawska, B.4
  • 24
    • 84868708721 scopus 로고    scopus 로고
    • Neuroprotective tri- and tetracyclic BChE inhibitors releasing reversible inhibitors upon carbamate transfer
    • Darras, F. H., Kling, B., Heilmann, J., and Decker, M. (2012) Neuroprotective tri- and tetracyclic BChE inhibitors releasing reversible inhibitors upon carbamate transfer ACS Med. Chem. Lett. 3, 914-919
    • (2012) ACS Med. Chem. Lett. , vol.3 , pp. 914-919
    • Darras, F.H.1    Kling, B.2    Heilmann, J.3    Decker, M.4
  • 25
    • 0042236906 scopus 로고    scopus 로고
    • Approach to the synthesis of (+)-Ifforestine. Model studies directed at the tetracyclic framework
    • Roos, G. H. P. and Drastlik, K. A. (2003) Approach to the synthesis of (+)-Ifforestine. Model studies directed at the tetracyclic framework Heterocycles 60, 2023-2044
    • (2003) Heterocycles , vol.60 , pp. 2023-2044
    • Roos, G.H.P.1    Drastlik, K.A.2
  • 26
    • 34548756072 scopus 로고    scopus 로고
    • A practical method for preparation of 4-hydroxyquinolinone esters
    • Beutner, G. L., Kuethe, J. T., and Yasuda, N. (2007) A practical method for preparation of 4-hydroxyquinolinone esters J. Org. Chem. 72, 7058-7061
    • (2007) J. Org. Chem. , vol.72 , pp. 7058-7061
    • Beutner, G.L.1    Kuethe, J.T.2    Yasuda, N.3
  • 27
    • 0001695638 scopus 로고
    • Novel ring enlargement of lactams via quinazolinone annelation. A facile route to benzoannelated large-membered cyclic 1,5-diamines
    • Takeuchi, H., Matsushita, Y., and Eguchi, S. (1991) Novel ring enlargement of lactams via quinazolinone annelation. A facile route to benzoannelated large-membered cyclic 1,5-diamines J. Org. Chem. 56, 1535-1537
    • (1991) J. Org. Chem. , vol.56 , pp. 1535-1537
    • Takeuchi, H.1    Matsushita, Y.2    Eguchi, S.3
  • 28
    • 13844253966 scopus 로고    scopus 로고
    • Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine
    • Decker, M. (2005) Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine Eur. J. Med. Chem. 40, 305-313
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 305-313
    • Decker, M.1
  • 29
    • 52049120810 scopus 로고    scopus 로고
    • Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase
    • Yücel, Y. Y., Tacal, Ö., and Özer, I. (2008) Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase Arch. Biochem. Biophys. 478, 201-205
    • (2008) Arch. Biochem. Biophys. , vol.478 , pp. 201-205
    • Yücel, Y.Y.1    Tacal, Ö.2    Özer, I.3
  • 31
    • 32044459019 scopus 로고    scopus 로고
    • Novel tricyclic quinazolinimines and related tetracyclic nitrogen bridgehead compounds as cholinesterase inhibitors with selectivity towards butyrylcholinesterase
    • Decker, M., Krauth, F., and Lehmann, J. (2006) Novel tricyclic quinazolinimines and related tetracyclic nitrogen bridgehead compounds as cholinesterase inhibitors with selectivity towards butyrylcholinesterase Bioorg. Med. Chem. 14, 1966-1977
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 1966-1977
    • Decker, M.1    Krauth, F.2    Lehmann, J.3
  • 34
  • 35
    • 84896483454 scopus 로고    scopus 로고
    • The PyMOL Molecular Graphics System, Version 1.6.0.0, Schrödinger, LLC
    • The PyMOL Molecular Graphics System, Version 1.6.0.0, Schrödinger, LLC.
  • 42
    • 52649126332 scopus 로고    scopus 로고
    • Phenylalanine 169 in the Second Extracellular Loop of the Human Histamine H4 Receptor Is Responsible for the Difference in Agonist Binding between Human and Mouse H4 Receptors
    • Lim, H. D., Jongejan, A., Bakker, R. A., Haaksma, E., de Esch, I. J. P., and Leurs, R. (2008) Phenylalanine 169 in the Second Extracellular Loop of the Human Histamine H4 Receptor Is Responsible for the Difference in Agonist Binding between Human and Mouse H4 Receptors J. Pharmacol. Exp. Ther. 327, 88-96
    • (2008) J. Pharmacol. Exp. Ther. , vol.327 , pp. 88-96
    • Lim, H.D.1    Jongejan, A.2    Bakker, R.A.3    Haaksma, E.4    De Esch, I.J.P.5    Leurs, R.6
  • 44
    • 84871788150 scopus 로고    scopus 로고
    • Species-dependent activities of G-protein-coupled receptor ligands: Lessons from histamine receptor orthologs
    • Strasser, A., Wittmann, H.-J., Buschauer, A., Schneider, E. H., and Seifert, R. (2013) Species-dependent activities of G-protein-coupled receptor ligands: lessons from histamine receptor orthologs Trends Pharmacol. Sci. 34, 13-32
    • (2013) Trends Pharmacol. Sci. , vol.34 , pp. 13-32
    • Strasser, A.1    Wittmann, H.-J.2    Buschauer, A.3    Schneider, E.H.4    Seifert, R.5
  • 46
    • 80755176833 scopus 로고    scopus 로고
    • Targeting the Histamine H4 Receptor
    • Marson, C. M. (2011) Targeting the Histamine H4 Receptor Chem. Rev. 111, 7121-7156
    • (2011) Chem. Rev. , vol.111 , pp. 7121-7156
    • Marson, C.M.1
  • 48
    • 66649096395 scopus 로고    scopus 로고
    • Conserved waters mediate structural and functional activation of family A (rhodopsin-like) G protein-coupled receptors
    • Angel, T. E., Chance, M. R., and Palczewski, K. (2009) Conserved waters mediate structural and functional activation of family A (rhodopsin-like) G protein-coupled receptors Proc. Natl. Acad. Sci. U.S.A. 106, 8555-8560
    • (2009) Proc. Natl. Acad. Sci. U.S.A. , vol.106 , pp. 8555-8560
    • Angel, T.E.1    Chance, M.R.2    Palczewski, K.3
  • 50
    • 37349122184 scopus 로고    scopus 로고
    • Pharmacological Profile of Histaprodifens at Four Recombinant Histamine H1 Receptor Species Isoforms
    • Straßer, A., Striegl, B., Wittmann, H.-J., and Seifert, R. (2008) Pharmacological Profile of Histaprodifens at Four Recombinant Histamine H1 Receptor Species Isoforms J. Pharmacol. Exp. Ther. 324, 60-71
    • (2008) J. Pharmacol. Exp. Ther. , vol.324 , pp. 60-71
    • Straßer, A.1    Striegl, B.2    Wittmann, H.-J.3    Seifert, R.4
  • 51
    • 70350050831 scopus 로고    scopus 로고
    • Synthesis and Structure-Activity Relationships of Cyanoguanidine-Type and Structurally Related Histamine H4 Receptor Agonists
    • Igel, P., Geyer, R., Strasser, A., Dove, S., Seifert, R., and Buschauer, A. (2009) Synthesis and Structure-Activity Relationships of Cyanoguanidine-Type and Structurally Related Histamine H4 Receptor Agonists J. Med. Chem. 52, 6297-6313
    • (2009) J. Med. Chem. , vol.52 , pp. 6297-6313
    • Igel, P.1    Geyer, R.2    Strasser, A.3    Dove, S.4    Seifert, R.5    Buschauer, A.6
  • 53
    • 84896460194 scopus 로고    scopus 로고
    • Molecular Operating Environment (MOE), 2011.10; Chemical Computing Group Inc. 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7
    • Molecular Operating Environment (MOE), 2011.10; Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2011.
    • (2011)
  • 54
    • 0028854034 scopus 로고
    • Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation
    • Jones, G., Willett, P., and Glen, R. C. (1995) Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation J. Mol. Biol. 245, 43-53
    • (1995) J. Mol. Biol. , vol.245 , pp. 43-53
    • Jones, G.1    Willett, P.2    Glen, R.C.3
  • 55
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G., Willett, P., Glen, R. C., Leach, A. R., and Taylor, R. (1997) Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 267, 727-748
    • (1997) J. Mol. Biol. , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5


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