메뉴 건너뛰기




Volumn 17, Issue 1, 2012, Pages 809-819

Comparative computational studies of 3,4-dihydro-2,6-diaryl-4-oxo- pyrimidine-5-carbonitrile derivatives as potential antinociceptive agents

Author keywords

4 (3H) pyrimidinones; Antinociceptive activity; Density functional theory; Molecular modeling

Indexed keywords

3,4 DIHYDRO 2 (4 CHLOROPHENYL) 6 (4 METHOXYPHENYL) 4 OXO PYRIMIDINE 5 CARBONITRILE; 3,4 DIHYDRO 2 PHENYL 6 PARA FLUOROPHENYL 4 OXO PYRIMIDINE 5 CARBONITRILE; 3,4-DIHYDRO-2-(4-CHLOROPHENYL)-6-(4-METHOXYPHENYL)-4-OXO-PYRIMIDINE-5-CARBONITRILE; 3,4-DIHYDRO-2-PHENYL-6-PARA-FLUOROPHENYL-4-OXO-PYRIMIDINE-5-CARBONITRILE; ACETIC ACID; ANALGESIC AGENT; NITRILE; PYRIMIDINE DERIVATIVE;

EID: 84856143924     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17010809     Document Type: Article
Times cited : (21)

References (45)
  • 1
    • 84944034682 scopus 로고
    • Pyrimidines and their benzoderivatives
    • Katritzky, A.R., Rees, C.W., Eds.; Pergamon Press: Oxford, UK
    • Brown, D.J. Pyrimidines and their benzoderivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A.R., Rees, C.W., Eds.; Pergamon Press: Oxford, UK, 1984; Volume 3, pp. 57-155.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 57-155
    • Brown, D.J.1
  • 2
    • 0642341455 scopus 로고
    • Analytical reactions of substituted pyrimidines
    • Singh, A.K. Analytical Reactions of Substituted Pyrimidines. Talanta 1982, 29, 95-102.
    • (1982) Talanta , vol.29 , pp. 95-102
    • Singh, A.K.1
  • 3
    • 0019233820 scopus 로고
    • Antineoplastic properties of pyrimidinone interferon inducers
    • Stringfellow, D.A. Antineoplastic properties of pyrimidinone interferon inducers. Adv. Enzyme Regul. 1981, 19, 335-348.
    • (1981) Adv. Enzyme Regul. , vol.19 , pp. 335-348
    • Stringfellow, D.A.1
  • 4
    • 0023940220 scopus 로고
    • Combined treatment of colon adenocarcinoma in rats with tumor necrosis factor and the interferon inducer ABPP
    • Marquet, R.L.; Eggermont, A.M.M.; de Bruin, R.W.F.; Fiers, W.; Jeekel, J. Combined treatment of colon adenocarcinoma in rats with tumor necrosis factor and the interferon inducer ABPP. J. Interferon Res. 1988, 8, 319-323.
    • (1988) J. Interferon Res. , vol.8 , pp. 319-323
    • Marquet, R.L.1    Eggermont, A.M.M.2    De Bruin, R.W.F.3    Fiers, W.4    Jeekel, J.5
  • 5
    • 0023143435 scopus 로고
    • Antitumor activity of pyrimidinones, a class of small-molecule biological response modifiers
    • Li, L.H.; Wallace, T.L.; Wierenga, W.; Skulnick, H.I.; DeKoning, T.F. Antitumor activity of pyrimidinones, a class of small-molecule biological response modifiers. J. Biol. Response Mod. 1987, 6, 44-55. (Pubitemid 17018253)
    • (1987) Journal of Biological Response Modifiers , vol.6 , Issue.1 , pp. 44-55
    • Li, L.H.1    Wallace, T.L.2    Wierenga, W.3
  • 6
    • 0025635996 scopus 로고
    • The antitumor activity of the interferon inducer bropirimine is partially mediated by endogenous tumor necrosis factor a
    • Scheringa, M.; Ijzermans, J.N.; Jeekel, J.; Marquet, R.L. The antitumor activity of the interferon inducer bropirimine is partially mediated by endogenous tumor necrosis factor a. Cancer Immunol. Immunother. 1990, 32, 251-255.
    • (1990) Cancer Immunol. Immunother. , vol.32 , pp. 251-255
    • Scheringa, M.1    Ijzermans, J.N.2    Jeekel, J.3    Marquet, R.L.4
  • 7
  • 8
    • 0032846847 scopus 로고    scopus 로고
    • Pharmacokinetic properties, induction of interferon, and efficacy of selected 5-halo-6-phenyl pyrimidinones, bropirimine analogues, in a model of severe experimental autoimmune encephalomyelitis
    • DOI 10.1016/S0192-0561(99)00040-5, PII S0192056199000405
    • Vroegop, S.M.; Chapman, D.L.; Decker, D.E.; Galinet, L.A.; Brideau, R.J.; Ready, K.A.; Dunn, C.J.; Buxser, S.E. Pharmacokinetic properties, induction of interferon, and efficacy of selected 5-halo-6-phenyl pyrimidinones, bropirimine analogues, in a model of severe experimental autoimmune encephalomyelitis. Int. J. Immunopharmacol. 1999, 21, 647-662. (Pubitemid 29440798)
    • (1999) International Journal of Immunopharmacology , vol.21 , Issue.10 , pp. 647-662
    • Vroegop, S.M.1    Chapman, D.L.2    Decker, D.E.3    Galinet, L.A.4    Brideau, R.J.5    Ready, K.A.6    Dunn, C.J.7    Buxser, S.E.8
  • 9
    • 0036236866 scopus 로고    scopus 로고
    • A new and efficient synthesis of substituted 6-[(2′-Dialkylamino) ethyl] pyrimidine and 4-N,N-Dialkyl-6-vinyl-cytosine derivatives and evaluation of their anti-Rubella activity
    • DOI 10.1016/S0968-0896(02)00077-9, PII S0968089602000779
    • Saladino, R.; Ciambecchini, U.; Maga, G.; Mastromarino, P.; Conti, C.; Botta, M.A. A new and efficient synthesis of substituted 6-[(2'-dialkylamino) ethyl] pyrimidine and 4-N,N-dialkyl-6-vinylcytosine derivatives and evaluation of their anti-rubella activity. Bioorg. Med. Chem. Lett. 2002, 10, 2143-2153. (Pubitemid 34450904)
    • (2002) Bioorganic and Medicinal Chemistry , vol.10 , Issue.7 , pp. 2143-2153
    • Saladino, R.1    Ciambecchini, U.2    Maga, G.3    Mastromarino, P.4    Conti, C.5    Botta, M.6
  • 10
    • 0033552903 scopus 로고    scopus 로고
    • Stereospecific synthesis, structure-activity relationship, and oral bioavailability of tetrahydropyrimidin-2-one HIV protease inhibitors
    • DOI 10.1021/jm9803626
    • de Lucca, G.V.; Liang, J.; de Lucca, I. Stereospecific synthesis, structure-activity relationship, and oral bioavailability of tetrahydropyrimidin-2-one HIV protease inhibitors. J. Med. Chem. 1999, 42, 135-152. (Pubitemid 29056495)
    • (1999) Journal of Medicinal Chemistry , vol.42 , Issue.1 , pp. 135-152
    • De Lucca, G.V.1    Liang, J.2    De Lucca, I.3
  • 14
    • 30544433446 scopus 로고    scopus 로고
    • Syntheses of vanadyl and zinc(II) complexes of 1-hydroxy-4,5,6- substituted 2(1H)-pyrimidinones and their insulin-mimetic activities
    • DOI 10.1016/j.jinorgbio.2005.11.010, PII S0162013405003375
    • Yamaguchi, M.; Wakasugi, K.; Saito, R.; Adachi, Y.; Yoshikawa, Y.; Sakurai, H.; Katoh, A. Syntheses of vanadyl and zinc(II) complexes of 1-hydroxy-4,5,6-substituted 2(1H)-pyrimidinones and their insulin-mimetic activities. J. Inorg. Biochem. 2006, 100, 260-269. (Pubitemid 43081921)
    • (2006) Journal of Inorganic Biochemistry , vol.100 , Issue.2 , pp. 260-269
    • Yamaguchi, M.1    Wakasugi, K.2    Saito, R.3    Adachi, Y.4    Yoshikawa, Y.5    Sakurai, H.6    Katoh, A.7
  • 15
    • 4644337416 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant evaluation of some new 2-substituted-3- arylpyrido[2,3-d]pyrimidinones
    • DOI 10.1016/j.bmc.2004.07.068, PII S0968089604005413
    • White, D.C.; Greenwood, T.D.; Downey, A.L.; Bloomquist, J.R.; Wolfe, J.F. Synthesis and anticonvulsant evaluation of some new 2-substituted-3- arylpyrido[2,3-d]pyrimidinones. Bioorg. Med. Chem. 2004, 12, 5711-5717. (Pubitemid 39304068)
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , Issue.21 , pp. 5711-5717
    • White, D.C.1    Greenwood, T.D.2    Downey, A.L.3    Bloomquist, J.R.4    Wolfe, J.F.5
  • 16
    • 0018717964 scopus 로고
    • Synthesis of 3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-2-carboxylates, a new series of orally active antiallergy agents
    • DOI 10.1021/jm00191a009
    • Temple, D.L.; Yevich, J.P.; Covington, R.R.; Hanning, C.A.; Seidehamel, R.J.; Mackey, H.K.; Bartek, M.J. Synthesis of 3,4-dihydro-4-oxothieno[2,3-d] pyrimidine-2-carboxylates, a new series of orally active antiallergy agents. J. Med. Chem. 1979, 22, 505-510. (Pubitemid 10230609)
    • (1979) Journal of Medicinal Chemistry , vol.22 , Issue.5 , pp. 505-510
    • Temple, D.L.1    Yevich, J.P.2    Covington, R.R.3
  • 17
    • 0027946480 scopus 로고
    • 5-Substituted 2,3-dihydro-6-mercapto-1,3-diphenyl-2-thioxo-4(3H)- pyrimidinones and their 6-(acylthio) derivatives with platelet antiaggregating, antiinflammatory, antiarrhythmic, antihyperlipidemic and other activities
    • Ranise, A.; Bruno, O.; Bondavalli, F.; Schenone, S.; D'Amico, M.; Falciani, M.; Filippelli, W.; Rossi, F. 5-Substituted 2,3-dihydro-6-mercapto-1, 3-diphenyl-2-thioxo-4(3H)-pyrimidinones and their 6-(acylthio) derivatives with platelet antiaggregating, antiinflammatory, antiarrhythmic, antihyperlipidemic and other activities. Farmaco 1994, 49, 551-558. (Pubitemid 24358700)
    • (1994) Farmaco , vol.49 , Issue.9 , pp. 551-558
    • Ranise, A.1    Bruno, O.2    Bondavalli, F.3    Schenone, S.4    D'Amico, M.5    Falciani, M.6    Filippelli, W.7    Rossi, F.8
  • 18
    • 0028220833 scopus 로고
    • Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazo[1,2-a]pyrimidine derivatives
    • DOI 10.1016/0223-5234(94)90097-3
    • Abignente, E.; Sacchi, A.; Laneri, S.; Rossi, F.; D'Amico, M.; Berrino, L.; Calderaro, V.; Parrillo, C. Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazo[1,2-a]pyrimidine derivatives. Eur. J. Med. Chem. 1994, 29, 279-286. (Pubitemid 24148835)
    • (1994) European Journal of Medicinal Chemistry , vol.29 , Issue.4 , pp. 279-286
    • Abignente, E.1    Sacchi, A.2    Laneri, S.3    Rossi, F.4    D'Amico, M.5    Berrino, L.6    Calderaro, V.7    Parrillo, C.8
  • 19
    • 56049107677 scopus 로고    scopus 로고
    • Estudo preliminar da toxicidade e das atividades anti-edematogênica e anti-nociceptiva da 3,4-diidro- 2-fenil-6-para-flúor-fenil-4-oxo- pirimidina-5-carbonitrila
    • dos Anjos, J.V.; Mendonça, F.J.B., Jr.; Costa-Silva, J.H.; de Souza, I.A.; de Melo, S.J. Estudo Preliminar da Toxicidade e das Atividades Anti-edematogênica e Anti-nociceptiva da 3,4-diidro- 2-fenil-6-para- flúor-fenil-4-oxo-pirimidina-5-carbonitrila. Lat. Am. J. Pharm. 2008, 27, 343.
    • (2008) Lat. Am. J. Pharm. , vol.27 , pp. 343
    • Dos Anjos, J.V.1    Mendonça Jr., F.J.B.2    Costa-Silva, J.H.3    De Souza, I.A.4    De Melo, S.J.5
  • 20
    • 0022449850 scopus 로고
    • Pyrimidinones. 3. N-substituted 6-phenylpyrimidinones and pyrimidinediones with diuretic/hypotensive and antiinflammatory activity
    • Skulnick, H.I.; Ludens, J.H.; Wendling, M.G.; Glenn, E.M.; Rohloff, N.A.; Smith, R.J.; Wierenga, W. Pyrimidinones. 3. N-substituted 6-phenylpyrimidinones and pyrimidinediones with diuretic/hypotensive and antiinflammatory activity. J. Med. Chem. 1986, 29, 1499-1504. (Pubitemid 16034645)
    • (1986) Journal of Medicinal Chemistry , vol.29 , Issue.8 , pp. 1499-1504
    • Skulnick, H.I.1    Ludens, J.H.2    Wendling, M.G.3
  • 21
    • 0031424454 scopus 로고    scopus 로고
    • Synthesis of 6-thiosubstituted 5-ethoxycarbonyl-1,3-diphenyl-2-thioxo-2, 3-dihydropyrimidin-4(1H)-ones, 6-substituted 5-hydroxy-1,3-diphenyl-2,3- dihydrothieno[2,3-d]pyrimidin-4(1H)-ones and their esters with local anesthetic, antiarrhythmic, antiinflammatory and analgesic activities
    • Ranise, A.; Bruno, O.; Schenone, S.; Bondavalli, F.; Falcone, G.; Filippelli, W.; Sorrentino, S. Synthesis of 6-thiosubstituted 5-ethoxycarbonyl-1,3-diphenyl-2-thioxo-2,3-dihydropyrimidin- 4(1H)-ones, 6-substituted 5-hydroxy-1,3-diphenyl-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)- ones and their esters with local anesthetic, antiarrhythmic, antiinflammatory and analgesic activities. Farmaco 1997, 52, 547-555. (Pubitemid 28067870)
    • (1997) Farmaco , vol.52 , Issue.8-9 , pp. 547-555
    • Ranise, A.1    Bruno, O.2    Schenone, S.3    Bondavalli, F.4    Falcone, G.5    Filippelli, W.6    Sorrentino, S.7
  • 22
    • 0033943596 scopus 로고    scopus 로고
    • Synthesis of new [1,3,4]thiadiazolo[3,2-a]thieno[2,3-d]pyrimidinone derivatives with antiinflammatory activity
    • Modica, M.; Santagati, M.; Santagati, A.; Cutuli, V.; Mangano, N.; Caruso, A. Synthesis of new [1,3,4]thiadiazolo[3,2-a]thieno[2,3-d]pyrimidinone derivatives with antiinflammatory activity. Pharmazie 2000, 55, 500-502.
    • (2000) Pharmazie , vol.55 , pp. 500-502
    • Modica, M.1    Santagati, M.2    Santagati, A.3    Cutuli, V.4    Mangano, N.5    Caruso, A.6
  • 23
    • 34250693141 scopus 로고    scopus 로고
    • Synthesis Reactions, and Anti-inflammatory activity of heterocyclic systems fused to a thiophene moiety using citrazinic acid as synthon
    • Amr, A.E.G.E.; Sabry, N.M.; Abdulla, M.M. Synthesis, Reactions, and Anti-inflammatory activity of heterocyclic systems fused to a thiophene moiety using citrazinic acid as synthon. Monatsh. Chem. 2007, 138, 699-707.
    • (2007) Monatsh. Chem. , vol.138 , pp. 699-707
    • Amr, A.E.G.E.1    Sabry, N.M.2    Abdulla, M.M.3
  • 25
    • 0022330577 scopus 로고
    • Antiviral and other bioactivities of pyrimidinones
    • Wierenga, W. Antiviral and other bioactivities of pyrimidinones. Pharmacol. Ther. 1985, 30, 67-89. (Pubitemid 16090530)
    • (1985) Pharmacology and Therapeutics , vol.30 , Issue.1 , pp. 67-89
    • Wierenga, W.1
  • 26
    • 0034519777 scopus 로고    scopus 로고
    • Biologically active dihydropyrimidones of the Biginelli-type - A literature survey
    • DOI 10.1016/S0223-5234(00)01189-2
    • Kappe, C.O. Biologically active dihydropyrimidones of the Biginelli-type-A literature survey. Eur. J. Med. Chem. 2000, 35, 1043-1052. (Pubitemid 32050011)
    • (2000) European Journal of Medicinal Chemistry , vol.35 , Issue.12 , pp. 1043-1052
    • Kappe, C.O.1
  • 27
    • 0026644122 scopus 로고
    • 5-Fluoro (3H) pyrimidine- 4-ones: Synthesis, reactivity and pharmacological properties
    • de Melo, S.J.; Luu-Duc, C.; Thomasson, F.; Narcisse, G.; Gaultier, C. 5-Fluoro (3H) pyrimidine- 4-ones: synthesis, reactivity and pharmacological properties. Ann. Pharm. Fr. 1992, 50, 39-51.
    • (1992) Ann. Pharm. Fr. , vol.50 , pp. 39-51
    • De Melo, S.J.1    Luu-Duc, C.2    Thomasson, F.3    Narcisse, G.4    Gaultier, C.5
  • 32
    • 34249331264 scopus 로고    scopus 로고
    • Novel strategies for inhibition of the p38 MAPK pathway
    • DOI 10.1016/j.tips.2007.04.008, PII S0165614707000879
    • Zhang, J.; Shen, B.; Lin, A. Novel strategies for inhibition of the p38 MAPK pathway. Trends Pharmacol. Sci. 2007, 28, 286-295. (Pubitemid 46818466)
    • (2007) Trends in Pharmacological Sciences , vol.28 , Issue.6 , pp. 286-295
    • Zhang, J.1    Shen, B.2    Lin, A.3
  • 34
    • 33644933323 scopus 로고    scopus 로고
    • Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines
    • Falcão, E.P.S.; de Melo, S.J.; Srivastava, R.M.; Catanho, M.T.J.A.; do Nascimento, S.C. Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines. Eur. J. Med. Chem. 2006, 41, 276-282.
    • (2006) Eur. J. Med. Chem. , vol.41 , pp. 276-282
    • Falcao, E.P.S.1    De Melo, S.J.2    Srivastava, R.M.3    Catanho, M.T.J.A.4    Do Nascimento, S.C.5
  • 35
    • 41149178688 scopus 로고    scopus 로고
    • Quantitative Structure Activity Relationships (QSAR) of 4-Amino-2,6-Diarylpyrimidine-5- Carbonitriles Having Anti-inflammatory Activity
    • da Silva, J.B.P.; Ramos, M.N.; Barros Neto, B.; de Melo, S.J.; Falcão, E.P.S.; Catanho, M.T.J.A. Quantitative Structure Activity Relationships (QSAR) of 4-Amino-2,6-Diarylpyrimidine-5- Carbonitriles Having Anti-inflammatory Activity. J. Braz. Chem. Soc. 2008, 19, 337.
    • (2008) J. Braz. Chem. Soc. , vol.19 , pp. 337
    • Da Silva, J.B.P.1    Ramos, M.N.2    Barros Neto, B.3    De Melo, S.J.4    Falcao, E.P.S.5    Catanho, M.T.J.A.6
  • 37
    • 0035246513 scopus 로고    scopus 로고
    • Cyclooxygenase inhibitors - Current status and future prospects
    • DOI 10.1016/S0223-5234(01)01197-7, PII S0223523401011977
    • Dannhardt, G.; Kiefer, W. Cyclooxygenase inhibitors-current status and future prospects. Eur. J. Med. Chem. 2001, 36, 109-126. (Pubitemid 32304514)
    • (2001) European Journal of Medicinal Chemistry , vol.36 , Issue.2 , pp. 109-126
    • Dannhardt, G.1    Kiefer, W.2
  • 38
    • 0000680650 scopus 로고
    • Acetic acid for analgesic screening
    • Koster, R.; Anderson, M.; de Beer, E.J. Acetic acid for analgesic screening. Fed. Proc. 1959, 18, 412-416.
    • (1959) Fed. Proc. , vol.18 , pp. 412-416
    • Koster, R.1    Anderson, M.2    De Beer, E.J.3
  • 39
    • 85057661551 scopus 로고    scopus 로고
    • CRC Press: Los Angeles, CA, USA
    • Kruger, L. Methods in Pain Research; CRC Press: Los Angeles, CA, USA, 2001; pp. 11-39.
    • (2001) Methods in Pain Research , pp. 11-39
    • Kruger, L.1
  • 41
    • 3042988525 scopus 로고
    • A hydrocarbon force-field utilizing V1 and V2 torsional terms
    • Allinger, N.L. A hydrocarbon force-field utilizing V1 and V2 torsional terms. J. Am. Chem. Soc. 1977, 99, 8127-8134.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127-8134
    • Allinger, N.L.1
  • 45
    • 84856162994 scopus 로고    scopus 로고
    • Spartan Model; Wavefunction Inc.: Irvine CA USA 2009. Available online, (accessed on 10 May)
    • SpartanModel; Wavefunction, Inc.: Irvine, CA, USA, 2009. Available online: http://www.wavefun.com/products/windows/SpartanModel/win-model.html (accessed on 10 May 2011).
    • (2011)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.