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Volumn 22, Issue 12, 2013, Pages 5922-5933

Novel 1,3-diarylpyrazole acrylamides: Synthesis, antiplatelet activity screening, and in silico evaluation studies

Author keywords

1,3 Diarylpyrazoles; Acryl amides; Antiplatelet activity; Arachidonic acid; Collagen

Indexed keywords

(2E) N (4 METHOXYBENZYL) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)ACRYLAMIDE; (2E) N BENZYL 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4YL)ACRYLAMIDE; (2E) N CYCLOHEXYL 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)ACRYLAMIDE; (2E) N CYCLOPROPYL 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)ACRYLAMIDE; (E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]ACRYLAMIDE; (E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]ACRYLIC ACID; 1 (2 ETHOXYPHENYL) 4 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL]PIPERAZINE; 1 (2 FUROYL) 4 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL]PIPERAZINE; 1 (2 METHOXYPHENYL) 4 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]PROP 2 ENOYL]PIPERAZINE; 1 (2,3 DIMETHYLPHENYL) 4 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL)1H PYRAZOL 4 YL]PROP 2 ENOYL]PIPERAZINE; 1 (3 CHLOROPHENYL) 4 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]PROP 2 ENOYL]PIPERAZINE; 1 (4 CHLOROPHENYL) 4 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]PROP 2 ENOYL]PIPERAZINE; 1 (4 METHYLPHENYL) 4 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]PROP 2 ENOYL]PIPERAZINE; 1 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL] 4 (2,3,4 TRIMETHOXYBENZYL)PIPERAZINE; 1 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL] 4 (TETRAHYDROFURAN 2 YL CARBONYL)PIPERAZINE; 1 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL] 4 PYRIDIN 4 YLPIPERAZINE; 1 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]PROP 2 ENOYL] 4 [3 (TRIFLUOROMETHYL)PHENYL]; 1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOLE 4 CARBALDEHYDE; 1 PHENYL 4 [(2E) 3 [1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL]PROP 2 ENOYL]PIPERAZINE; 2 (2 {4 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL]PIPERAZINE 1 YL}ETHOXY)ETHANOL; 2 {4 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL]PIPERAZINE 1 YL}PYRIMIDINE; 4 (1 (2 PHENYLHYDRAZONO)ETHYL)PYRIDINE; 4 [(2E) 3 (1 PHENYL 3 (PYRIDIN 4 YL) 1H PYRAZOL 4 YL)PROP 2 ENOYL]MORPHOLINE; 4 {4 [(1E) 3 (4 BENZYLPIPERIDIN 1 YL) 3 OXOPROP 1 EN 1 YL] 1 PHENYL 1H PYRAZOL 3 YL}PYRIDINE; 4 {4 [(1E) 3 OXO 3 (PIPERIDIN 1 YL)PROP 1 EN 1 YL] 1 PHENYL 1H PYRAZOL 3 YL}PYRIDINE; ACRYLAMIDE DERIVATIVE; ANTITHROMBOCYTIC AGENT; ARACHIDONIC ACID; UNCLASSIFIED DRUG;

EID: 84886094540     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0580-x     Document Type: Article
Times cited : (6)

References (34)
  • 1
    • 67649836274 scopus 로고    scopus 로고
    • Comparative studies on conventional and microwave-assisted synthesis of a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a]pyrimidines and their antimicrobial activities
    • 10.2478/s11532-009-0023-1 1:CAS:528:DC%2BD1MXns1OntbY%3D
    • Algul O, Meric A, Polat S, Yuksek ND, Serin MS (2009) Comparative studies on conventional and microwave-assisted synthesis of a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a]pyrimidines and their antimicrobial activities. Cent Eur J Chem 7:337-342
    • (2009) Cent Eur J Chem , vol.7 , pp. 337-342
    • Algul, O.1    Meric, A.2    Polat, S.3    Yuksek, N.D.4    Serin, M.S.5
  • 2
    • 0024827770 scopus 로고
    • Thromboxane A2: Its generation and role in platelet activation
    • 2534976 10.1016/0163-7827(89)90002-7 1:CAS:528:DyaK3cXmtVCrt78%3D
    • Arita H, Hansaki K (1989) Thromboxane A2: its generation and role in platelet activation. Prog Lipid Res 28:273-301
    • (1989) Prog Lipid Res , vol.28 , pp. 273-301
    • Arita, H.1    Hansaki, K.2
  • 3
    • 80054828281 scopus 로고    scopus 로고
    • Synthesis, characterization, and biological screening of some novel thiazolidin-4-one and alpha-aminophosphonate derivatives
    • 10.1080/10426507.2010.550268 1:CAS:528:DC%2BC3MXhtlagtLbJ
    • Badadhe PV, Chavan NM, Ghotekar S, Mandhane PG, Joshi RS, Gill CH (2011) Synthesis, characterization, and biological screening of some novel thiazolidin-4-one and alpha-aminophosphonate derivatives. Phosphorus Sulfur and Silicon Relat Elem 186:2021-2032
    • (2011) Phosphorus Sulfur and Silicon Relat Elem , vol.186 , pp. 2021-2032
    • Badadhe, P.V.1    Chavan, N.M.2    Ghotekar, S.3    Mandhane, P.G.4    Joshi, R.S.5    Gill, C.H.6
  • 4
    • 84859827026 scopus 로고    scopus 로고
    • Synthesis, anti-inflammatory, antiplatelet and in silico evaluations of (E)-3-(3-(2,3-dihydro-3-methyl-2-oxo-3H-benzoxazole-6-yl)-1-phenyl-1H-pyrazole- 4-yl)acrylamides
    • 1:CAS:528:DC%2BC38XovFamt7o%3D
    • Baytas S, Turan Dural NN, Özkan Y, Simsek HB, Gürsel T, Ünlü S (2012) Synthesis, anti-inflammatory, antiplatelet and in silico evaluations of (E)-3-(3-(2,3-dihydro-3-methyl-2-oxo-3H-benzoxazole-6-yl)-1- phenyl-1H-pyrazole-4-yl)acrylamides. Turk J Chem 36:367-382
    • (2012) Turk J Chem , vol.36 , pp. 367-382
    • Baytas, S.1    Turan Dural, N.N.2    Özkan, Y.3    Simsek, H.B.4    Gürsel, T.5    Ünlü, S.6
  • 5
    • 0035120357 scopus 로고    scopus 로고
    • Novel platelet inhibitors
    • 11160773 10.1146/annurev.med.52.1.161 1:CAS:528:DC%2BD3MXhs1KhsLg%3D
    • Bennett JS (2001) Novel platelet inhibitors. Annu Rev Med 52:161-184
    • (2001) Annu Rev Med , vol.52 , pp. 161-184
    • Bennett, J.S.1
  • 6
    • 0033187329 scopus 로고    scopus 로고
    • The thienopyridines in coronary artery disease
    • 10980841 10.1007/s11886-999-0022-z 1:STN:280:DC%2BD3M%2FlsF2rtQ%3D%3D
    • Berger PB (1999) The thienopyridines in coronary artery disease. Curr Cardiol Rep 1:192-198
    • (1999) Curr Cardiol Rep , vol.1 , pp. 192-198
    • Berger, P.B.1
  • 7
    • 78651139188 scopus 로고
    • The aggregation of blood platelet
    • 14056485 1:CAS:528:DyaF3sXkvVCht7s%3D
    • Born G, Cross M (1963) The aggregation of blood platelet. J Physiol 168:178-195
    • (1963) J Physiol , vol.168 , pp. 178-195
    • Born, G.1    Cross, M.2
  • 8
    • 18844443185 scopus 로고    scopus 로고
    • Aromatase inhibitors in the treatment of breast cancer
    • 15814851 10.1210/er.2004-0015 1:CAS:528:DC%2BD2MXltVWru7w%3D
    • Brueggemeier RW, Hackett JC, Diaz-Cruz ES (2005) Aromatase inhibitors in the treatment of breast cancer. Endocr Rev 26:331-345
    • (2005) Endocr Rev , vol.26 , pp. 331-345
    • Brueggemeier, R.W.1    Hackett, J.C.2    Diaz-Cruz, E.S.3
  • 9
    • 0347895930 scopus 로고
    • 4-Pyridylhydantoins
    • 10.1021/jo01104a623 1:CAS:528:DyaG1MXjvF2hsA%3D%3D
    • Chu CC, Teague PC (1958) 4-Pyridylhydantoins. J Org Chem 23:1578
    • (1958) J Org Chem , vol.23 , pp. 1578
    • Chu, C.C.1    Teague, P.C.2
  • 10
    • 0021847311 scopus 로고
    • Plaque fissuring-the cause of acute myocardial infarction, sudden ischaemic death, and crescendo angina
    • 10.1136/hrt.53.4.363
    • Davis MJ, Thomas AC (1985) Plaque fissuring-the cause of acute myocardial infarction, sudden ischaemic death, and crescendo angina. Br Heart J 53:363-373
    • (1985) Br Heart J , vol.53 , pp. 363-373
    • Davis, M.J.1    Thomas, A.C.2
  • 11
    • 2142684003 scopus 로고    scopus 로고
    • New developments on thromboxane and prostacyclin modulators. Part II: Prostacyclin modulators
    • 15134517 10.2174/0929867043365279
    • De Leval X, Hanson J, David JL, Masereel B, Pirotte B, Dogne JM (2004) New developments on thromboxane and prostacyclin modulators. Part II: prostacyclin modulators. Curr Med Chem 11:1243-1252
    • (2004) Curr Med Chem , vol.11 , pp. 1243-1252
    • De Leval, X.1    Hanson, J.2    David, J.L.3    Masereel, B.4    Pirotte, B.5    Dogne, J.M.6
  • 12
    • 0034609833 scopus 로고    scopus 로고
    • Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties
    • 11020286 10.1021/jm000942e 1:CAS:528:DC%2BD3cXmsFeitb4%3D
    • Ertl P, Rohde B, Selzer P (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714-3717
    • (2000) J Med Chem , vol.43 , pp. 3714-3717
    • Ertl, P.1    Rohde, B.2    Selzer, P.3
  • 13
    • 66349127675 scopus 로고    scopus 로고
    • Synthesis of c-nitro aliphaticmethyl esters via Michael additions promoted by microwave irradiation
    • 19384288 10.3390/molecules14041595 1:CAS:528:DC%2BD1MXltlGitb8%3D
    • Escalante J, Diaz-Coutino FD (2009) Synthesis of c-nitro aliphaticmethyl esters via Michael additions promoted by microwave irradiation. Molecules 14:1595-1604
    • (2009) Molecules , vol.14 , pp. 1595-1604
    • Escalante, J.1    Diaz-Coutino, F.D.2
  • 14
    • 0027125530 scopus 로고
    • The pathogenesis of coronary artery disease and the acute coronary syndromes (1)
    • 1727977 10.1056/NEJM199201233260406 1:STN:280:DyaK38%2FptlSgtg%3D%3D
    • Fuster V, Badimon L, Badimon JJ, Chesebro JH (1992) The pathogenesis of coronary artery disease and the acute coronary syndromes (1). N Engl J Med 326:242-250
    • (1992) N Engl J Med , vol.326 , pp. 242-250
    • Fuster, V.1    Badimon, L.2    Badimon, J.J.3    Chesebro, J.H.4
  • 15
    • 84886099511 scopus 로고    scopus 로고
    • http://www.molinspiration.com/cgi-bin/properties
  • 16
    • 84886095475 scopus 로고    scopus 로고
    • http://www.organic-chemistry.org/prog/peo
  • 17
    • 0242300217 scopus 로고    scopus 로고
    • Antiplatelet therapy: In search of the 'magic bullet'
    • 14526381 10.1038/nrd1198 1:CAS:528:DC%2BD3sXnslarsb8%3D
    • Jackson SP, Schoenwaelder SM (2003) Antiplatelet therapy: in search of the 'magic bullet'. Nat Rev Drug Discov 2:775-789
    • (2003) Nat Rev Drug Discov , vol.2 , pp. 775-789
    • Jackson, S.P.1    Schoenwaelder, S.M.2
  • 18
    • 34748905199 scopus 로고    scopus 로고
    • Environmentally benign synthesis of sydnone containing 1,3,4-thiadiazines under microwave and solvent free conditions
    • 10.1007/s12039-007-0040-6
    • Jyothi C, Rai SN, Kalluraya B (2007) Environmentally benign synthesis of sydnone containing 1,3,4-thiadiazines under microwave and solvent free conditions. J Chem Sci 119:299-302
    • (2007) J Chem Sci , vol.119 , pp. 299-302
    • Jyothi, C.1    Rai, S.N.2    Kalluraya, B.3
  • 19
    • 54849435698 scopus 로고    scopus 로고
    • Microwave assisted one-pot synthesis of some 2,5-disubstituted 1,3,4-oxadiazoles
    • 1:CAS:528:DC%2BD1cXptVejtbc%3D
    • Kalluraya B, Rao JN, Sujith KV (2008) Microwave assisted one-pot synthesis of some 2,5-disubstituted 1,3,4-oxadiazoles. Indian J Heterocycl Chem 17:359-362
    • (2008) Indian J Heterocycl Chem , vol.17 , pp. 359-362
    • Kalluraya, B.1    Rao, J.N.2    Sujith, K.V.3
  • 20
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • 11259830 10.1016/S0169-409X(00)00129-0 1:CAS:528:DC%2BD3MXitVOhs7o%3D
    • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3-26
    • (2001) Adv Drug Deliv Rev , vol.46 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 21
    • 0019813114 scopus 로고
    • Highly selective inhibitors of thromboxane synthetase. 1 Imidazole derivatives
    • 10.1021/jm00142a005
    • Lizuka K, Akahane K, Momose D, Nakazawa M (1981) Highly selective inhibitors of thromboxane synthetase. 1 Imidazole derivatives. J Med Chem 24:1139-1148
    • (1981) J Med Chem , vol.24 , pp. 1139-1148
    • Lizuka, K.1    Akahane, K.2    Momose, D.3    Nakazawa, M.4
  • 22
    • 0023139858 scopus 로고
    • The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction
    • 3820396 1:CAS:528:DyaL2sXhsFSiu70%3D
    • Loo MH, Egan D, Vaughan ED, Marion D, Felsen D, Weisman S (1987) The effect of the thromboxane A2 synthesis inhibitor OKY-046 on renal function in rabbits following release of unilateral ureteral obstruction. J Urol 137:571-576
    • (1987) J Urol , vol.137 , pp. 571-576
    • Loo, M.H.1    Egan, D.2    Vaughan, E.D.3    Marion, D.4    Felsen, D.5    Weisman, S.6
  • 23
    • 24944494905 scopus 로고    scopus 로고
    • Aspirin resistance and atherothrombotic disease
    • 16168280 10.1016/j.jacc.2004.08.070 1:CAS:528:DC%2BD2MXhtVWhu7vK
    • Mason PJ, Jacobs AK, Freedman JE (2005) Aspirin resistance and atherothrombotic disease. J Am Coll Cardiol 46:986-993
    • (2005) J Am Coll Cardiol , vol.46 , pp. 986-993
    • Mason, P.J.1    Jacobs, A.K.2    Freedman, J.E.3
  • 24
    • 0036846748 scopus 로고    scopus 로고
    • Aspirin resistance in cardiovascular disease: A review of prevalence, mechanisms, and clinical significance
    • 12428082 1:CAS:528:DC%2BD38Xptleis70%3D
    • McKee SA, Sane DC, Deliargyris EN (2002) Aspirin resistance in cardiovascular disease: a review of prevalence, mechanisms, and clinical significance. Thromb Haemost 88:711-715
    • (2002) Thromb Haemost , vol.88 , pp. 711-715
    • McKee, S.A.1    Sane, D.C.2    Deliargyris, E.N.3
  • 26
    • 0142195896 scopus 로고    scopus 로고
    • Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease
    • 14592549 10.1016/S0049-3848(03)00382-7 1:CAS:528:DC%2BD3sXosVyhs7w%3D
    • Patrignani P (2003) Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res 110:281-286
    • (2003) Thromb Res , vol.110 , pp. 281-286
    • Patrignani, P.1
  • 27
    • 0029009904 scopus 로고
    • Antiplatelet drugs: A comparative review
    • 10.2165/00003495-199550010-00002
    • Schros K (1995) Antiplatelet drugs: a comparative review. Drugs 50:7-28
    • (1995) Drugs , vol.50 , pp. 7-28
    • Schros, K.1
  • 30
    • 0034954596 scopus 로고    scopus 로고
    • The P2Y12 receptor as a therapeutic target in cardiovascular disease
    • 11454254 10.1080/09537100120058739 1:CAS:528:DC%2BD3MXkvFWhu7Y%3D
    • Storey F (2001) The P2Y12 receptor as a therapeutic target in cardiovascular disease. Platelets 12:197-209
    • (2001) Platelets , vol.12 , pp. 197-209
    • Storey, F.1
  • 32
    • 27344449477 scopus 로고    scopus 로고
    • Computing chemistry on the web
    • 16257371 10.1016/S1359-6446(05)03584-1
    • Tetko IV (2005) Computing chemistry on the web. Drug Discov Today 10:1497-1500
    • (2005) Drug Discov Today , vol.10 , pp. 1497-1500
    • Tetko, I.V.1
  • 33
    • 0025280866 scopus 로고
    • Platelet hyperreactivity and prognosis in survivors of myocardial infarction
    • 2336086 10.1056/NEJM199005313222201 1:STN:280:DyaK3c3ksFSmtA%3D%3D
    • Trip MD, Cats VM, Capelle FJL, Vreeken J (1990) Platelet hyperreactivity and prognosis in survivors of myocardial infarction. N Engl J Med 322:1549-1554
    • (1990) N Engl J Med , vol.322 , pp. 1549-1554
    • Trip, M.D.1    Cats, V.M.2    Capelle, F.J.L.3    Vreeken, J.4
  • 34
    • 0035960630 scopus 로고    scopus 로고
    • Global burden of cardiovascular diseases: Part I: General considerations, the epidemiologic transition, risk factors, and impact of urbanization
    • 11723030 10.1161/hc4601.099487 1:STN:280:DC%2BD3Mnns1yjsw%3D%3D
    • Yusuf S, Reddy S, Ounpuu S, Anand S (2001) Global burden of cardiovascular diseases: part I: general considerations, the epidemiologic transition, risk factors, and impact of urbanization. Circulation 104:2746-2753
    • (2001) Circulation , vol.104 , pp. 2746-2753
    • Yusuf, S.1    Reddy, S.2    Ounpuu, S.3    Anand, S.4


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