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Volumn 5, Issue 17, 2013, Pages 2037-2056

5-alkyl-1,3-oxazole derivatives of 6-amino-nicotinic acids as alkyl ester bioisosteres are antagonists of the P2Y12 receptor

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 OXADIAZOLE DERIVATIVE; 3 METHYL ISOXAZOLE; 5 METHYL DIHYDRO OXAZOLE; ALKYL GROUP; ANTITHROMBOCYTIC AGENT; CYTOCHROME P450; N (5 CHLOROTHIOPHEN 2 YLSULFONYL) 4 [3 CYANO 5 (5 ETHYL OXAZOL 2 YL) 6 METHYLPYRIDIN 2 YL]PIPERAZIN 1 CARBOXAMIDE; OXAZOLE DERIVATIVE; PURINERGIC P2Y RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

EID: 84887945666     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.13.171     Document Type: Article
Times cited : (11)

References (55)
  • 3
    • 0033821625 scopus 로고    scopus 로고
    • ADP is not an agonist at P2X1 receptors: Evidence for separate receptors stimulated by ATP and ADP on human platelets
    • Mahaut-Smith M.P., Ennion SJ, Rolf M.G., Evans RJ ADP is not an agonist at P2X1 receptors: evidence for separate receptors stimulated by ATP and ADP on human platelets. Br. J. Pharmacol. 131(1), 108-114 (2000).
    • (2000) Br. J. Pharmacol. , vol.131 , Issue.1 , pp. 108-114
    • Mahaut-Smith, M.P.1    Ennion, S.J.2    Rolf, M.G.3    Evans, R.J.4
  • 4
    • 33744999455 scopus 로고    scopus 로고
    • 12 receptor
    • DOI 10.2174/138161206776361318
    • Storey R.F. Biology and pharmacology of the platelet P2Y12 receptor. Curr. Pharm. Design 12(10), 1255-1259 (2006). (Pubitemid 44082134)
    • (2006) Current Pharmaceutical Design , vol.12 , Issue.10 , pp. 1255-1259
    • Storey, R.F.1
  • 5
    • 75949128633 scopus 로고    scopus 로고
    • Antiplatelet therapies for the treatment of cardiovascular disease
    • Michelson AD. Antiplatelet therapies for the treatment of cardiovascular disease. Nat. Rev. Drug Discov. 9(2), 154-169 (2010).
    • (2010) Nat. Rev. Drug Discov. , vol.9 , Issue.2 , pp. 154-169
    • Michelson, A.D.1
  • 6
    • 77949499925 scopus 로고    scopus 로고
    • 12 receptor antagonists in development
    • 12 receptor antagonists in development. Eur. Heart J. Suppl. 10(Suppl. I), I33-I37 (2008).
    • (2008) Eur. Heart J. Suppl. , vol.10 , Issue.SUPPL. I
    • Cattaneo, M.1
  • 7
    • 0033678468 scopus 로고    scopus 로고
    • Identification and biological activity of the active metabolite of clopidogrel
    • Savi P, Pereillo JM, Uzabiaga MF et al. Identification and biological activity of the active metabolite of clopidogrel. Thromb. Haemost. 84, 891-896. (2000).
    • (2000) Thromb. Haemost. , vol.84 , pp. 891-896
    • Savi, P.1    Pereillo, J.M.2    Uzabiaga, M.F.3
  • 10
    • 77949360232 scopus 로고    scopus 로고
    • 12 antagonists for inhibition of platelet aggregation
    • 12 antagonists for inhibition of platelet aggregation. J. Med. Chem. 53(5), 2010-2037 (2010).
    • (2010) J. Med. Chem. , vol.53 , Issue.5 , pp. 2010-2037
    • Parlow, J.J.1    Burney, M.W.2    Case, B.L.3
  • 19
    • 84878689243 scopus 로고    scopus 로고
    • Synthesis, structure-property relationships and pharmacokinetic evaluation of ethyl 6-aminonicotinate sulfonylureas as antagonists of the P2Y12 receptor
    • Bach P, Boström J, Brickmann K et al. Synthesis, structure-property relationships and pharmacokinetic evaluation of ethyl 6-aminonicotinate sulfonylureas as antagonists of the P2Y12 receptor. Eur. J. Med. Chem. 65, 360-375 (2013).
    • (2013) Eur. J. Med. Chem. , vol.65 , pp. 360-375
    • Bach, P.1    Boström, J.2    Brickmann, K.3
  • 20
    • 84884224776 scopus 로고    scopus 로고
    • 12 receptor. Separation in vivo of antithrombotic effect and bleeding for candidate drug AZD1283
    • 12 receptor. Separation in vivo of antithrombotic effect and bleeding for candidate drug AZD1283. J. Med. Chem. 56(17), 7015-7024(2013).
    • (2013) J. Med. Chem. , vol.56 , Issue.17 , pp. 7015-7024
    • Bach, P.1    Antonsson, T.2    Bylund, R.3
  • 21
    • 79955419410 scopus 로고    scopus 로고
    • Synopsis of some recent tactical application of bioisosteres in drug design
    • Meanwell NA. Synopsis of some recent tactical application of bioisosteres in drug design. J. Med. Chem. 54(8), 2529-2591 (2011).
    • (2011) J. Med. Chem. , vol.54 , Issue.8 , pp. 2529-2591
    • Meanwell, N.A.1
  • 22
    • 77952732009 scopus 로고    scopus 로고
    • Bioisosteric replacement and scaffold hopping in lead generation and optimization
    • Langdon SR, Ertl P, Brown N. Bioisosteric replacement and scaffold hopping in lead generation and optimization. Mol. Inf. 29(5), 366-385 (2010).
    • (2010) Mol. Inf. , vol.29 , Issue.5 , pp. 366-385
    • Langdon, S.R.1    Ertl, P.2    Brown, N.3
  • 23
    • 11844255399 scopus 로고    scopus 로고
    • Bioisosterism: A useful strategy for molecular modification and drug design
    • Lima LM, Barreiro EJ Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem. 12, 23-49 (2005). (Pubitemid 40089827)
    • (2005) Current Medicinal Chemistry , vol.12 , Issue.1 , pp. 23-49
    • Lima, L.M.1    Barreiro, E.J.2
  • 25
    • 84876857819 scopus 로고    scopus 로고
    • Potent fibrinolysis inhibitor discovered by shape and electrostatic complementarity to the drug tranexamic acid
    • Boström J., Grant JA, Fjellström O, Thelin A., Gustafsson D. Potent fibrinolysis inhibitor discovered by shape and electrostatic complementarity to the drug tranexamic acid. J. Med. Chem. 56(8), 3273-3280 (2013).
    • (2013) J. Med. Chem. , vol.56 , Issue.8 , pp. 3273-3280
    • Boström, J.1    Grant, J.A.2    Fjellström, O.3    Thelin, A.4    Gustafsson, D.5
  • 27
    • 0035952991 scopus 로고    scopus 로고
    • An improved synthesis of 1,2,4-oxadiazoles on solid support
    • DOI 10.1016/S0960-894X(01)00028-2, PII S0960894X01000282
    • Rice KD, Nuss JM An improved synthesis of 1,2,4-oxadiazoles on solid support. Bioorg. Med. Chem. Lett. 11(6), 753-755 (2001). (Pubitemid 32230672)
    • (2001) Bioorganic and Medicinal Chemistry Letters , vol.11 , Issue.6 , pp. 753-755
    • Rice, K.D.1    Nuss, J.M.2
  • 28
    • 15144349042 scopus 로고
    • A study of the proton nuclear magnetic resonance spectra of aryl and monoand disubstituted N-methylazones
    • Butler RN. A study of the proton nuclear magnetic resonance spectra of aryl and monoand disubstituted N-methylazones. Can. J. Chem. 51, 2315-2322 (1973).
    • (1973) Can. J. Chem. , vol.51 , pp. 2315-2322
    • Butler, R.N.1
  • 29
    • 0000345938 scopus 로고
    • A new synthesis of highly functionalized oxazoles
    • Wipf P, Miller CP A new synthesis of highly functionalized oxazoles. J. Org. Chem. 58(14), 3604-3606 (1993).
    • (1993) J. Org. Chem. , vol.58 , Issue.14 , pp. 3604-3606
    • Wipf, P.1    Miller, C.P.2
  • 31
    • 0030054110 scopus 로고    scopus 로고
    • The chemistry of pseudomonic acid. 15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles
    • DOI 10.1021/jm9503862
    • Brown P, Davies DT, O'Hanlo PJ, Wilson JM The chemistry of pseudomonic acid (VIII). Part 15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles. J. Med. Chem. 39(2), 446-457 (1996). (Pubitemid 26041457)
    • (1996) Journal of Medicinal Chemistry , vol.39 , Issue.2 , pp. 446-457
    • Brown, P.1    Davies, D.T.2    O'Hanlon, P.J.3    Wilson, J.M.4
  • 32
    • 14544306016 scopus 로고    scopus 로고
    • Efficient conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-one to pyrimidines via PyBroP-mediated coupling
    • DOI 10.1021/jo040281j
    • Kang F-A, Kodah J., Guan Q, Li X, Murray W V. Efficient conversion of Biginelli 3,4-dihydropyrimidin-2(1H)-one to pyrimidines via PyBrop-mediated coupling. J. Org. Chem. 70 (5), 1957-1960 (2005). (Pubitemid 40300171)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.5 , pp. 1957-1960
    • Kang, F.-A.1    Kodah, J.2    Guan, Q.3    Li, X.4    Murray, W.V.5
  • 33
    • 0021813940 scopus 로고
    • On the calculation of electrostatic interactions in proteins
    • DOI 10.1016/0022-2836(85)90297-9
    • Gilson MK, Rashin A, Fine R., Honig B. On the calculation of electrostatic interactions in proteins. J. Mol. Biol. 184, 503-516 (1985). (Pubitemid 15013023)
    • (1985) Journal of Molecular Biology , vol.184 , Issue.3 , pp. 503-516
    • Gilson, M.K.1    Rashin, A.2    Fine, R.3    Honig, B.4
  • 35
    • 69249213604 scopus 로고    scopus 로고
    • 12 independently from ADP but antagonizes ADP-induced receptor signaling and platelet aggregation
    • 12 independently from ADP but antagonizes ADP-induced receptor signaling and platelet aggregation. J. Thromb. Haemost. 7(9), 1556-1565 (2009).
    • (2009) J. Thromb. Haemost. , vol.7 , Issue.9 , pp. 1556-1565
    • Van Giezen, J.J.J.1    Nilsson, L.2    Berntsson, P.3
  • 37
    • 77957114353 scopus 로고    scopus 로고
    • Predictability of idiosyncratic drug toxicity risk for carboxylic acid-containing drugs based on the chemical stability of acyl glucuronide
    • Sawamura R, Okudaira N, Watanabe K et al. Predictability of idiosyncratic drug toxicity risk for carboxylic acid-containing drugs based on the chemical stability of acyl glucuronide. Drug. Metab. Dispos. 38(10), 1857-1864 (2010).
    • (2010) Drug. Metab. Dispos. , vol.38 , Issue.10 , pp. 1857-1864
    • Sawamura, R.1    Okudaira, N.2    Watanabe, K.3
  • 40
    • 0011639217 scopus 로고    scopus 로고
    • Oxygen and nitrogen in competitive situations: Which is the hydrogen-bond acceptor?
    • Böhm H-J, Klebe, G, Brode S, Hesse U. Oxygen and nitrogen in competitive situations: which is the hydrogen-bond acceptor? Chem. Eur. J. 2, 1509-1513 (1996).
    • (1996) Chem. Eur. J. , vol.2 , pp. 1509-1513
    • Böhm, H.-J.1    Klebe, G.2    Brode, S.3    Hesse, U.4
  • 41
    • 66249086550 scopus 로고    scopus 로고
    • Hydrogen bonding, electrostatic potential, and molecular design
    • Kenny PW. Hydrogen bonding, electrostatic potential, and molecular design. J. Chem. Inf. Model. 49(5), 1234-1244 (2009).
    • (2009) J. Chem. Inf. Model. , vol.49 , Issue.5 , pp. 1234-1244
    • Kenny, P.W.1
  • 42
    • 37049077770 scopus 로고
    • Prediction of hydrogen bond basicity from computed molecular electrostatic properties: Implications for comparative molecular field ana lysis
    • Kenny PW. Prediction of hydrogen bond basicity from computed molecular electrostatic properties: implications for comparative molecular field ana lysis. J. Chem. Soc. Perkin. Trans. 2 (2), 199-202 (1994).
    • (1994) J. Chem. Soc. Perkin. Trans. , vol.2 , Issue.2 , pp. 199-202
    • Kenny, P.W.1
  • 43
    • 0000346476 scopus 로고
    • Correlations between the solvent hydrogen bond acceptor parameter b and the calculated molecular electrostatic potential
    • Murray JS, Ranganathan S, Politzer P. Correlations between the solvent hydrogen bond acceptor parameter b and the calculated molecular electrostatic potential. J. Org. Chem. 56(11), 3734-3737 (1991).
    • (1991) J. Org. Chem. , vol.56 , Issue.11 , pp. 3734-3737
    • Murray, J.S.1    Ranganathan, S.2    Politzer, P.3
  • 44
    • 0025955501 scopus 로고
    • Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor
    • Orlek BS, Blaney FE, Brown F et al. Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor. J. Med. Chem. 34(9), 2726-2735 (1991).
    • (1991) J. Med. Chem. , vol.34 , Issue.9 , pp. 2726-2735
    • Orlek, B.S.1    Blaney, F.E.2    Brown, F.3
  • 46
    • 0026776275 scopus 로고
    • Synthesis and muscarinic activities of quinuclidin-3-yltriazole and -tetrazole derivatives
    • Wadsworth HJ, Jenkins SM, Orlek BS et al. Synthesis and muscarinic activities of quinuclidin-3-yltriazole and -tetrazole derivatives. J. Med. Chem. 35(7), 1280-1290 (1992).
    • (1992) J. Med. Chem. , vol.35 , Issue.7 , pp. 1280-1290
    • Wadsworth, H.J.1    Jenkins, S.M.2    Orlek, B.S.3
  • 47
    • 33745078578 scopus 로고    scopus 로고
    • The use of three-dimensional shape and electrostatic similarity searching in the identification of a melanin-concentrating hormone receptor 1 antagonist
    • DOI 10.1111/j.1747-0285.2006.00341.x
    • Muchmore SW, Souers AJ, Akritopoulou-Zanze I. The use of three-dimensional shape and electrostatic similarity searching in the identification of a melanin-concentrating hormone receptor 1 antagonist. Chem. Biol. Drug Des. 67(2), 174-176 (2006). (Pubitemid 43881377)
    • (2006) Chemical Biology and Drug Design , vol.67 , Issue.2 , pp. 174-176
    • Muchmore, S.W.1    Souers, A.J.2    Akritopoulou-Zanze, I.3
  • 48
    • 62649161780 scopus 로고    scopus 로고
    • Identification of a chemical probe for NAADP by virtual screening
    • Naylor E, Arredouani A, Vasudevan SR et al. Identification of a chemical probe for NAADP by virtual screening. Nat. Chem. Biol. 5, 220-226 (2009).
    • (2009) Nat. Chem. Biol. , vol.5 , pp. 220-226
    • Naylor, E.1    Arredouani, A.2    Vasudevan, S.R.3
  • 49
    • 77749315417 scopus 로고    scopus 로고
    • Lipophilicity in drug discovery
    • Waring MJ. Lipophilicity in drug discovery. Expert Opin. Drug Dis. 5, 235-248 (2010).
    • (2010) Expert Opin. Drug Dis. , vol.5 , pp. 235-248
    • Waring, M.J.1
  • 50
    • 79956223090 scopus 로고    scopus 로고
    • Comparison of three GPCR structural templates for modeling of the P2Y12 nucloetide receptor
    • Deflorian F, Jacobsen KA Comparison of three GPCR structural templates for modeling of the P2Y12 nucloetide receptor. J. Comput. Aided Mol. Des. 25, 329-338 (2011).
    • (2011) J. Comput. Aided Mol. Des. , vol.25 , pp. 329-338
    • Deflorian, F.1    Jacobsen, K.A.2
  • 51
    • 33750981540 scopus 로고    scopus 로고
    • Do structurally similar ligands bind in a similar fashion?
    • DOI 10.1021/jm060167o
    • Boström J., Hogner A, Schmitt S. Do structurally similar ligands bind in a similar fashion? J. Med. Chem. 49(23), 6716-6725 (2006). (Pubitemid 44749739)
    • (2006) Journal of Medicinal Chemistry , vol.49 , Issue.23 , pp. 6716-6725
    • Bostrom, J.1    Hogner, A.2    Schmitt, S.3
  • 52
    • 0000826617 scopus 로고    scopus 로고
    • Hydrogen bonding properties of oxygen and nitrogen acceptors in aromatic heterocycles
    • Nobeli I, Price SL, Lommerse JPM, Taylor R. Hydrogen bonding properties of oxygen and nitrogen acceptors in aromatic heterocycles. J. Comput. Chem. 18(16), 2060-2074 (1997). (Pubitemid 127598558)
    • (1997) Journal of Computational Chemistry , vol.18 , Issue.16 , pp. 2060-2074
    • Nobeli, I.1    Price, S.L.2    Lommerse, J.P.M.3    Taylor, R.4
  • 53
    • 67650763061 scopus 로고    scopus 로고
    • The pKBHX database. Toward a better understanding of hydrogen-bond basicity for medicinal chemists
    • Laurence C, Brameld KA, Graton JRM, Le Questel J-Y, Renault E. The pKBHX Database. toward a better understanding of hydrogen-bond basicity for medicinal chemists. J. Med. Chem. 52(14), 4073-4086 (2009).
    • (2009) J. Med. Chem. , vol.52 , Issue.14 , pp. 4073-4086
    • Laurence, C.1    Brameld, K.A.2    Graton, J.R.M.3    Le Questel, J.-Y.4    Renault, E.5
  • 54
    • 62649161780 scopus 로고    scopus 로고
    • Identification of a chemical probe for NAADP by virtual screening
    • Churchill GC. Identification of a chemical probe for NAADP by virtual screening. Nat. Chem. Biol. 4, 220-226 (2009).
    • (2009) Nat. Chem. Biol. , vol.4 , pp. 220-226
    • Churchill, G.C.1


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