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Volumn 22, Issue 11, 2013, Pages 5610-5616

Design, synthesis, and biologic evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents

Author keywords

Aromatic substitution; Cancer cell lines; Cytotoxicity; N Arylpyrazole; Pyrazole

Indexed keywords

1 (4 NITROPHENYL) 4 [4 (TRIFLUOROMETHYL)PHENYL] 1H PYRAZOLE; 1,2 BIS(3,5 DIMETHYL 1H PYRAZOL 4 YL)BENZENE; 1,2 BIS[3,5 DIMETHYL 1 (4 NITROPHENYL)PYRAZOL 4 YL]BENZENE; 1,3 BIS(3,5 DIMETHYL 1H PYRAZOL 4 YL)BENZENE; 1,3 BIS[3,5 DIMETHYL 1 (4 NITROPHENYL)PYRAZOL 4 YL]BENZENE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 4 (1H PYRAZOL 4 YL)PYRIDINE; 4 (4 NITROPHENYL) 1 (4 NITROPHENYL) 1H PYRAZOLE; 4 (4 NITROPHENYL) 1H PYRAZOLE; 4 [1 (4 NITROPHENYL) 1H PYRAZOL 4 YL]PYRIDINE; 4 [3,5 BIS(TRIFLUOROMETHYL)PHENYL] 1 (4 NITROPHENYL) 1H PYRAZOLE; 4 [3,5 BIS(TRIFLUOROMETHYL)PHENYL] 1H PYRAZOLE; 4 [4 (TRIFLUOROMETHYL)PHENYL] 1H PYRAZOLE; 4,4' [5 (OCTYLOXY) 1,3 PHENYLENE]BIS(3,5 DIMETHYL 1H PYRAZOLE); 4,4' [5 (OCTYLOXY) 1,3 PHENYLENE]BIS[3,5 DIMETHYL 1 (4 NITROPHENYL)PYRAZOLE]; BENZENE DERIVATIVE; CARBON; CISPLATIN; CYTOTOXIC AGENT; HYDROGEN; NITROGEN; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84887477070     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-013-0552-1     Document Type: Article
Times cited : (9)

References (33)
  • 4
    • 0037028635 scopus 로고    scopus 로고
    • Why do cyclo-oxygenase-2 inhibitors cause cardiovascular events?
    • 11823092 10.1016/S0735-1097(01)01749-1 1:CAS:528:DC%2BD38XitFOju7c%3D
    • Bing RJ, Lomnicka M (2002) Why do cyclo-oxygenase-2 inhibitors cause cardiovascular events? J Am Coll Cardiol 39(3):521-522
    • (2002) J Am Coll Cardiol , vol.39 , Issue.3 , pp. 521-522
    • Bing, R.J.1    Lomnicka, M.2
  • 6
    • 0037148587 scopus 로고    scopus 로고
    • Regioselective synthesis of pyrazoles via the ring cleavage of 3-substituted N-alkylated 3-hydroxyisoindolin-1-ones
    • Chang KT, Choi YH, Kim SH, Yoon YJ, Lee WS (2002) Regioselective synthesis of pyrazoles via the ring cleavage of 3-substituted N-alkylated 3-hydroxyisoindolin-1-ones. J Chem Soc, Perkin Trans 1:207-210
    • (2002) J Chem Soc, Perkin Trans , vol.1 , pp. 207-210
    • Chang, K.T.1    Choi, Y.H.2    Kim, S.H.3    Yoon, Y.J.4    Lee, W.S.5
  • 7
    • 64349120396 scopus 로고    scopus 로고
    • Synthesis of celecoxib analogues possessing a N-difluoromethyl-1,2- dihydropyrid-2-one 5-lipoxygenase pharmacophore: Biological evaluation as dual Inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity
    • 19296694 10.1021/jm8015188 1:CAS:528:DC%2BD1MXit1eksLk%3D
    • Chowdhury MA, Abdellatif KRA, Dong Y, Das D, Suresh MR, Knaus EE (2009) Synthesis of celecoxib analogues possessing a N-difluoromethyl-1,2-dihydropyrid- 2-one 5-lipoxygenase pharmacophore: biological evaluation as dual Inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. J Med Chem 52(6):1525-1529
    • (2009) J Med Chem , vol.52 , Issue.6 , pp. 1525-1529
    • Chowdhury, M.A.1    Abdellatif, K.R.A.2    Dong, Y.3    Das, D.4    Suresh, M.R.5    Knaus, E.E.6
  • 8
    • 31544452101 scopus 로고    scopus 로고
    • New trends in synthesis of pyrazole nucleosides as new antimetabolites
    • 16270665 10.1081/NCN-200067421 1:CAS:528:DC%2BD2MXhtF2ktr7E
    • Elgemeie GH, Zaghary WA, Amin KM, Nasr TM (2005) New trends in synthesis of pyrazole nucleosides as new antimetabolites. Nucleosides Nucleotides Nucleic Acids 24(8):1227-1247
    • (2005) Nucleosides Nucleotides Nucleic Acids , vol.24 , Issue.8 , pp. 1227-1247
    • Elgemeie, G.H.1    Zaghary, W.A.2    Amin, K.M.3    Nasr, T.M.4
  • 9
    • 38749095499 scopus 로고    scopus 로고
    • Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives
    • 17962022 10.1016/j.bmc.2007.10.015 1:CAS:528:DC%2BD1cXhsF2jsr8%3D
    • Farag AM, Mayhoub AS, Barakat SE, Bayomi AH (2008) Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives. Bioorg Med Chem 16(2):881-889
    • (2008) Bioorg Med Chem , vol.16 , Issue.2 , pp. 881-889
    • Farag, A.M.1    Mayhoub, A.S.2    Barakat, S.E.3    Bayomi, A.H.4
  • 10
    • 0037533953 scopus 로고    scopus 로고
    • Discovery of a potent and selective series of pyrazole bacterial methionyl-tRNA synthetase inhibitors
    • 12798340 10.1016/S0960-894X(03)00298-1 1:CAS:528:DC%2BD3sXksVaktLc%3D
    • Finn J, Mattia K, Morytko M, Ram S, Yang YF, Wu XM, Mak E, Gallant P, Keith D (2003) Discovery of a potent and selective series of pyrazole bacterial methionyl-tRNA synthetase inhibitors. Bioorg Med Chem Lett 13(13):2231-2234
    • (2003) Bioorg Med Chem Lett , vol.13 , Issue.13 , pp. 2231-2234
    • Finn, J.1    Mattia, K.2    Morytko, M.3    Ram, S.4    Yang, Y.F.5    Wu, X.M.6    Mak, E.7    Gallant, P.8    Keith, D.9
  • 11
    • 0034624679 scopus 로고    scopus 로고
    • Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3- and 4-substituted derivatives
    • 10715167 10.1021/jm990383f 1:CAS:528:DC%2BD3cXpsV2gsg%3D%3D
    • Genin MJ, Biles C, Keiser BJ, Poppe SM, Swaney SM, Tarpley WG, Yagi Y, Romero DL (2000) Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives. J Med Chem 43:1034-1040
    • (2000) J Med Chem , vol.43 , pp. 1034-1040
    • Genin, M.J.1    Biles, C.2    Keiser, B.J.3    Poppe, S.M.4    Swaney, S.M.5    Tarpley, W.G.6    Yagi, Y.7    Romero, D.L.8
  • 12
    • 0037319206 scopus 로고    scopus 로고
    • Microwave-assisted solution-phase synthesis of 1,4,5-trisubstituted pyrazoles
    • 10.1002/ejoc.200390091
    • Giacomelli G, Porcheddu A, Salaris M, Taddei M (2003) Microwave-assisted solution-phase synthesis of 1,4,5-trisubstituted pyrazoles. Eur J Org Chem 3:537-541
    • (2003) Eur J Org Chem , vol.3 , pp. 537-541
    • Giacomelli, G.1    Porcheddu, A.2    Salaris, M.3    Taddei, M.4
  • 13
    • 0035974649 scopus 로고    scopus 로고
    • Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: Replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere
    • 11520213 10.1021/jm010153c 1:CAS:528:DC%2BD3MXlsFygtbs%3D
    • Habeeb AG, Rao PNP, Knaus EE (2001) Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere. J Med Chem 44(18):3039-3042
    • (2001) J Med Chem , vol.44 , Issue.18 , pp. 3039-3042
    • Habeeb, A.G.1    Rao, P.N.P.2    Knaus, E.E.3
  • 14
    • 77955322921 scopus 로고    scopus 로고
    • Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents
    • 20594863 10.1016/j.bmc.2010.06.013 1:CAS:528:DC%2BC3cXoslagtL0%3D
    • Insuasty B, Tigreros A, Orozco F, Quiroga J, Abonía R, Nogueras M, Sanchez A, Cobo J (2010) Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents. Bioorg Med Chem 18(14):4965-4974
    • (2010) Bioorg Med Chem , vol.18 , Issue.14 , pp. 4965-4974
    • Insuasty, B.1    Tigreros, A.2    Orozco, F.3    Quiroga, J.4    Abonía, R.5    Nogueras, M.6    Sanchez, A.7    Cobo, J.8
  • 17
    • 0034794463 scopus 로고    scopus 로고
    • A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles
    • 11481007 10.1021/ja016226z 1:CAS:528:DC%2BD3MXltVWru7o%3D
    • Klapars A, Antilla JC, Huang X, Buchwald SL (2001) A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles. J Am Chem Soc 123(21):7727-7729
    • (2001) J Am Chem Soc , vol.123 , Issue.21 , pp. 7727-7729
    • Klapars, A.1    Antilla, J.C.2    Huang, X.3    Buchwald, S.L.4
  • 19
    • 33750091655 scopus 로고    scopus 로고
    • Design and synthesis of polypyrazolyl compounds as a new type of versatile building blocks
    • 10.1002/cjoc.200690228 1:CAS:528:DC%2BD28XpvF2qur8%3D
    • Li SH, Huang HP, Yu SY, Li XP (2006) Design and synthesis of polypyrazolyl compounds as a new type of versatile building blocks. Chin J Chem 24(9):1225-1229
    • (2006) Chin J Chem , vol.24 , Issue.9 , pp. 1225-1229
    • Li, S.H.1    Huang, H.P.2    Yu, S.Y.3    Li, X.P.4
  • 20
    • 34547166940 scopus 로고    scopus 로고
    • 2 fragments linked by 4,4′-bipyrazolyl, 1,4-bis(4′- pyrazolyl)benzene, and 4,4′-bipyridazine: Synthesis, structures, and magnetic properties
    • 10.1002/ejic.200700317
    • 2 fragments linked by 4,4′-bipyrazolyl, 1,4-bis(4′-pyrazolyl)benzene, and 4,4′-bipyridazine: synthesis, structures, and magnetic properties. Eur J Inorg Chem 20:3217-3226
    • (2007) Eur J Inorg Chem , vol.20 , pp. 3217-3226
    • Lozan, V.1    Solntsev, P.Y.2    Leibeling, G.3    Domasevitch, K.V.4    Kersting, B.5
  • 21
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • 6606682 10.1016/0022-1759(83)90303-4 1:STN:280:DyaL2c%2FovFSmtw%3D%3D
    • Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55-63
    • (1983) J Immunol Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 22
    • 28044473878 scopus 로고    scopus 로고
    • Regioselective synthesis of 1-aryl-3,4- substituted/annulated-5- (methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles
    • 16292836 10.1021/jo051771u 1:CAS:528:DC%2BD2MXhtFWrsrzN
    • Peruncheralathan S, Khan TA, Ila H, Junjappa H (2005) Regioselective synthesis of 1-aryl-3,4- substituted/annulated-5-(methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles. J Org Chem 70:10030-10035
    • (2005) J Org Chem , vol.70 , pp. 10030-10035
    • Peruncheralathan, S.1    Khan, T.A.2    Ila, H.3    Junjappa, H.4
  • 23
    • 38949175741 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3- aryl-4-pyrazolyl) chromones
    • 17555846 10.1016/j.ejmech.2007.04.004 1:CAS:528:DC%2BD1cXitlajsLw%3D
    • Prakash O, Kumar R, Parkash V (2008) Synthesis and antifungal activity of some new 3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromones. Eur J Med Chem 43(2):435-440
    • (2008) Eur J Med Chem , vol.43 , Issue.2 , pp. 435-440
    • Prakash, O.1    Kumar, R.2    Parkash, V.3
  • 24
    • 0000578869 scopus 로고
    • Molecular rearrangements during solvolyses of pentaoxyphosphoranes. Polyketones derived from phthalaldehyde and terephthalaldehyde
    • 10.1021/jo01286a058 1:CAS:528:DyaF1cXht1Sruw%3D%3D
    • Ramirez F, Bhatia SB, Patwardhan AV, Smith CP (1967) Molecular rearrangements during solvolyses of pentaoxyphosphoranes. polyketones derived from phthalaldehyde and terephthalaldehyde. J Org Chem 32:3547-3553
    • (1967) J Org Chem , vol.32 , pp. 3547-3553
    • Ramirez, F.1    Bhatia, S.B.2    Patwardhan, A.V.3    Smith, C.P.4
  • 25
    • 0037205947 scopus 로고    scopus 로고
    • 1,3-Diphenylpyrazoles: Synthesis and antiparasitic activities of azomethine derivatives
    • 12161064 10.1016/S0223-5234(02)01388-0 1:CAS:528:DC%2BD38XlvVGhu7k%3D
    • Rathelot P, Azas N, El-Kashef H, Delmas F, Giorgio CD, Timon-David P, Maldonado J, Vanelle P (2002) 1,3-Diphenylpyrazoles: synthesis and antiparasitic activities of azomethine derivatives. Eur J Med Chem 37(8):671-679
    • (2002) Eur J Med Chem , vol.37 , Issue.8 , pp. 671-679
    • Rathelot, P.1    Azas, N.2    El-Kashef, H.3    Delmas, F.4    Giorgio, C.D.5    Timon-David, P.6    Maldonado, J.7    Vanelle, P.8
  • 27
    • 0345306230 scopus 로고    scopus 로고
    • Polysubstituted pyrazoles, part 5.Synthesis of new 1-(4-chlorophenyl)-4- hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents
    • 14642328 10.1016/j.ejmech.2003.08.003 1:CAS:528:DC%2BD3sXpt1KrsLk%3D
    • Rostom SAF, Shalaby MA, El-Demellawy MA (2003) Polysubstituted pyrazoles, part 5.Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents. Eur J Med Chem 38(11-12):959-974
    • (2003) Eur J Med Chem , vol.38 , Issue.11-12 , pp. 959-974
    • Rostom, S.A.F.1    Shalaby, M.A.2    El-Demellawy, M.A.3
  • 28
    • 79958200235 scopus 로고    scopus 로고
    • Recent advances in the chemistry of pyrazoles. Properties, biological activities, and syntheses
    • 10.2174/138527211795378263 1:CAS:528:DC%2BC3MXlvFKrs78%3D
    • Schmidt A, Dreger A (2011) Recent advances in the chemistry of pyrazoles. Properties, biological activities, and syntheses. Curr Org Chem 15:1423-1463
    • (2011) Curr Org Chem , vol.15 , pp. 1423-1463
    • Schmidt, A.1    Dreger, A.2
  • 29
    • 33750893617 scopus 로고    scopus 로고
    • Synthesis and anti-microbial activity of pyrazolylbisindoles-promising anti-fungal compounds
    • 17029797 10.1016/j.bmcl.2006.09.019 1:CAS:528:DC%2BD28XhtF2jsrrI
    • Sivaprasad G, Perumal PT, Prabavathy VR, Mathivanan N (2006) Synthesis and anti-microbial activity of pyrazolylbisindoles-promising anti-fungal compounds. Bioorg Med Chem Lett 16:6302-6305
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 6302-6305
    • Sivaprasad, G.1    Perumal, P.T.2    Prabavathy, V.R.3    Mathivanan, N.4
  • 30
    • 2142640434 scopus 로고    scopus 로고
    • 2O coated Cu nanoparticles and their successful applications to Ullmann-type amination coupling reactions of aryl chlorides
    • 10.1039/b316147a
    • 2O coated Cu nanoparticles and their successful applications to Ullmann-type amination coupling reactions of aryl chlorides. Chem Commun 7:778-779
    • (2004) Chem Commun , vol.7 , pp. 778-779
    • Son, S.U.1    Park, I.K.2    Park, J.3    Hyeon, T.4
  • 32
    • 0000385688 scopus 로고    scopus 로고
    • Regioselective synthesis of unsymmetrical 3,5-dialkyl-1-arylpyrazoles
    • 11009357 10.1021/ol0001822 1:CAS:528:DC%2BD3cXmtV2hsbw%3D
    • Wang XJ, Tan J, Zhang L (2000) Regioselective synthesis of unsymmetrical 3,5-dialkyl-1-arylpyrazoles. Org Lett 2:3107-3109
    • (2000) Org Lett , vol.2 , pp. 3107-3109
    • Wang, X.J.1    Tan, J.2    Zhang, L.3
  • 33
    • 20844435969 scopus 로고    scopus 로고
    • Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles
    • 15960520 10.1021/jo0504464 1:CAS:528:DC%2BD2MXktFCgtL8%3D
    • Zhang H, Cai Q, Ma D (2005) Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles. J Org Chem 70:5164-5173
    • (2005) J Org Chem , vol.70 , pp. 5164-5173
    • Zhang, H.1    Cai, Q.2    Ma, D.3


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