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Volumn 20, Issue 1, 2012, Pages

4-Aryl-4H-naphthopyrans derivatives: One-pot synthesis, evaluation of Src kinase inhibitory and anti-proliferative activities

Author keywords

Anticancer activity; Carbonitrile; Naphthopyrans; Protein kinase; Src kinase

Indexed keywords

2 AMINO 4 ARYL 4H NAPHTOPYRAN 3 CARBONITRILE DERIVATIVE; ALDEHYDE; ANTINEOPLASTIC AGENT; DOXORUBICIN; NAPHTHALENE DERIVATIVE; PHOSPHATE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 84878544941     PISSN: 15608115     EISSN: 20082231     Source Type: Journal    
DOI: 10.1186/2008-2231-20-100     Document Type: Article
Times cited : (50)

References (38)
  • 1
    • 2942618768 scopus 로고    scopus 로고
    • A renaissance for SRC
    • Yeatman TJ: A renaissance for SRC. Nat Rev Cancer 2004, 4:470-480. (Pubitemid 38745532)
    • (2004) Nature Reviews Cancer , vol.4 , Issue.6 , pp. 470-480
    • Yeatman, T.J.1
  • 2
    • 0029069540 scopus 로고
    • Enhanced DNA-binding activity of a stat3-related protein in cells transformed by the src oncoprotein
    • Yu CL, Meyer DJ, Campbell GS, Larner AC, Carter-Su C, Schwartz J, Jove R: Enhanced DNA-binding activity of a Stat3-related protein in cells transformed by the Src oncoprotein. Science 1995, 269:81-83.
    • (1995) Science , vol.269 , pp. 81-83
    • Yu, C.L.1    Meyer, D.J.2    Campbell, G.S.3    Larner, A.C.4    Carter-Su, C.5    Schwartz, J.6    Jove, R.7
  • 5
    • 2442623056 scopus 로고    scopus 로고
    • SRC: Regulation, role in human carcinogenesis and pharmacological inhibitors
    • DOI 10.2174/1381612043384457
    • Tsygankov AY, Shore SK: Src: regulation, role in human carcinogenesis and pharmacological inhibitors. Curr Pharm Des 2004, 10:1745-1756. (Pubitemid 38647457)
    • (2004) Current Pharmaceutical Design , vol.10 , Issue.15 , pp. 1745-1756
    • Tsygankov, A.Y.1    Shore, S.K.2
  • 6
    • 0034668172 scopus 로고    scopus 로고
    • Induction and regulation of epithelialmesenchymal transitions
    • Boyer B, Valles AM, Edme N: Induction and regulation of epithelialmesenchymal transitions. Biochem Pharmacol 2000, 60:1091-1099.
    • (2000) Biochem Pharmacol , vol.60 , pp. 1091-1099
    • Boyer, B.1    Valles, A.M.2    Edme, N.3
  • 7
    • 36949032298 scopus 로고    scopus 로고
    • Src family nonreceptor tyrosine kinases as molecular targets for cancer therapy
    • DOI 10.2174/187152007784111278
    • Johnson FM, Gallick GE: SRC family nonreceptor tyrosine kinases as molecular targets for cancer therapy. Anticancer Agents Med Chem 2007, 7:651-659. (Pubitemid 350237770)
    • (2007) Anti-Cancer Agents in Medicinal Chemistry , vol.7 , Issue.6 , pp. 651-659
    • Johnson, F.M.1    Gallick, G.E.2
  • 8
    • 0035992434 scopus 로고    scopus 로고
    • Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis
    • Nam JS, Ino Y, Sakamoto M, Hirohashi S: Src family kinase inhibitor PP2 restores the E-cadherin/catenin cell adhesion system in human cancer cells and reduces cancer metastasis. Clin Cancer Res 2002, 8:2430-2436. (Pubitemid 34753619)
    • (2002) Clinical Cancer Research , vol.8 , Issue.7 , pp. 2430-2436
    • Nam, J.-S.1    Ino, Y.2    Sakamoto, M.3    Hirohashi, S.4
  • 9
    • 33644532202 scopus 로고    scopus 로고
    • Ski-606 decreases growth and motility of colorectal cancer cells by preventing pp 60(c-Src)-dependent tyrosine phosphorylation of betacatenin and its nuclear signaling
    • Coluccia AM, Benati D, Dekhil H, De Filippo A, Lan C, Gambacorti-Passerini C: SKI-606 decreases growth and motility of colorectal cancer cells by preventing pp 60(c-Src)-dependent tyrosine phosphorylation of betacatenin and its nuclear signaling. Cancer Res 2006, 66:2279-2286.
    • (2006) Cancer Res , vol.66 , pp. 2279-2286
    • Coluccia, A.M.1    Benati, D.2    Dekhil, H.3    De Filippo, A.4    Lan, C.5    Gambacorti-Passerini, C.6
  • 11
    • 45849109148 scopus 로고    scopus 로고
    • Src family kinases as potential therapeutic targets for malignancies and immunological disorders
    • DOI 10.2174/092986708784310404
    • Benati D, Baldari CT: SRC family kinases as potential therapeutic targets for malignancies and immunological disorders. Curr Med Chem 2008, 15:1154-1165. (Pubitemid 351997805)
    • (2008) Current Medicinal Chemistry , vol.15 , Issue.12 , pp. 1154-1165
    • Benati, D.1    Baldari, C.T.2
  • 16
    • 14644413418 scopus 로고    scopus 로고
    • Further studies on ethenyl and ethynyl-4-phenylamino-3- quinolinecarbonitriles: Identification of a subnanomolar Src kinase inhibitor
    • DOI 10.1016/j.bmcl.2005.01.004
    • Barrios Sosa AC, Boschelli DH, Wu B, Wang Y, Golas JM: Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: identification of a subnanomolar Src kinase inhibitor. Bioorg Med Chem Lett 2005, 15:1743-1747. (Pubitemid 40312563)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.6 , pp. 1743-1747
    • Sosa, A.C.B.1    Boschelli, D.H.2    Wu, B.3    Wang, Y.4    Golas, J.M.5
  • 17
    • 38049024511 scopus 로고    scopus 로고
    • Facile preparation of new 4-phenylamino-3-quinolinecarbonitrile Src kinase inhibitors via 7-fluoro intermediates: Identification of potent 7-Amino analogs
    • Boschelli DH, Wu B, Ye F, Durutlic H, Golas JM, Lucas J, Boschelli F: Facile preparation of new 4-phenylamino-3-quinolinecarbonitrile Src kinase inhibitors via 7-fluoro intermediates: identification of potent 7-Amino analogs. Bioorg Med Chem 2008, 16:405-412.
    • (2008) Bioorg Med Chem , vol.16 , pp. 405-412
    • Boschelli, D.H.1    Wu, B.2    Ye, F.3    Durutlic, H.4    Golas, J.M.5    Lucas, J.6    Boschelli, F.7
  • 19
    • 76649114346 scopus 로고    scopus 로고
    • Saracatinib. Dual Src/ABL kinase inhibitor, oncolytic
    • Dulsat C, Mealy N, Castaner R: Saracatinib. Dual Src/ABL kinase inhibitor, Oncolytic. Drugs Fut 2009, 34:106-114.
    • (2009) Drugs Fut , vol.34 , pp. 106-114
    • Dulsat, C.1    Mealy, N.2    Castaner, R.3
  • 21
    • 34547744408 scopus 로고    scopus 로고
    • + all
    • DOI 10.1358/dof.2007.032.06.1107656
    • Boschelli DH, Boschelli F: Bosutinib. Dual Src and Abl kinase inhibitor, treatment of solid tumors, treatment of CML and Ph+ ALL. Drugs Fut 2007, 32:481-490. (Pubitemid 47234738)
    • (2007) Drugs of the Future , vol.32 , Issue.6 , pp. 481-490
    • Boschelli, D.H.1    Boschelli, F.2
  • 22
    • 0031887743 scopus 로고    scopus 로고
    • Protein kinase inhibitors: The tyrosine-specific protein kinases
    • DOI 10.1016/S0163-7258(97)00052-1, PII S0163725897000521
    • Lawrence DS, Niu J: Protein kinase inhibitors: The tyrosine-specific protein kinases. Pharmacol Ther 1998, 77:81-114. (Pubitemid 28077909)
    • (1998) Pharmacology and Therapeutics , vol.77 , Issue.2 , pp. 81-114
    • Lawrence, D.S.1    Niu, J.2
  • 23
    • 0029778978 scopus 로고    scopus 로고
    • Synthesis and antiproliferative activity of tyrphostins containing quinoline moieties
    • Brunton VG, Lear MJ, McKeown P, Robins DJ, Workman P: Synthesis and antiproliferative activity of tyrphostins containing quinoline moieties. Anticancer Drug Des 1996, 11:463-483. (Pubitemid 26320793)
    • (1996) Anti-Cancer Drug Design , vol.11 , Issue.6 , pp. 463-483
    • Brunton, V.G.1    Lear, M.J.2    McKeown, P.3    Robins, D.J.4    Workman, P.5
  • 24
    • 0034722893 scopus 로고    scopus 로고
    • From oncogene to drug: Development of small molecule tyrosine kinase inhibitors as anti-tumor and anti-angiogenic agents
    • DOI 10.1038/sj.onc.1204102
    • Morin MJ: From oncogene to drug: development of small molecule tyrosine kinase inhibitors as anti-Tumor and anti-Angiogenic agents. Oncogene 2000, 19:6574-6583. (Pubitemid 32197695)
    • (2000) Oncogene , vol.19 , Issue.56 , pp. 6574-6583
    • Morin, M.J.1
  • 25
    • 0031837707 scopus 로고    scopus 로고
    • Antiproliferative naphthopyrans: Biological activity, mechanistic studies and therapeutic potential
    • Dell CP: Antiproliferative naphthopyrans: biological activity, mechanistic studies and therapeutic potential. Current Med Chem 1998, 5:179-194. (Pubitemid 28238488)
    • (1998) Current Medicinal Chemistry , vol.5 , Issue.3 , pp. 179-194
    • Dell, C.P.1
  • 29
    • 78650512265 scopus 로고    scopus 로고
    • Click chemistry inspired one-pot synthesis of 1, 4-disubstituted 1, 2, 3-Triazoles and their Src kinase inhibitory activity
    • Kumar D, Reddy VB, Kumar A, Mandal D, Tiwari R, Parang K: Click chemistry inspired one-pot synthesis of 1, 4-disubstituted 1, 2, 3-Triazoles and their Src kinase inhibitory activity. Bioorg Med Chem Lett 2011, 21:449-452.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 449-452
    • Kumar, D.1    Reddy, V.B.2    Kumar, A.3    Mandal, D.4    Tiwari, R.5    Parang, K.6
  • 31
    • 77955801058 scopus 로고    scopus 로고
    • Synthesis and evaluation of conformationally constrained peptide analogues as the src SH3 domain binding ligands
    • Tiwari R, Brown A, Narramaneni S, Sun G, Parang K: Synthesis and evaluation of conformationally constrained peptide analogues as the Src SH3 domain binding ligands. Biochimie 2010, 92:1153-1163.
    • (2010) Biochimie , vol.92 , pp. 1153-1163
    • Tiwari, R.1    Brown, A.2    Narramaneni, S.3    Sun, G.4    Parang, K.5
  • 32
    • 48949093663 scopus 로고    scopus 로고
    • Synthesis and evaluation of 3- phenylpyrazolo[3, 4-d]pyrimidine-peptide conjugates as Src kinase inhibitors
    • Kumar A, Wang Y, Lin X, Sun G, Parang K: Synthesis and evaluation of 3- phenylpyrazolo[3, 4-d]pyrimidine-peptide conjugates as Src kinase inhibitors. Chem Med Chem 2007, 2:13460-1360.
    • (2007) Chem Med Chem , vol.2 , pp. 13460-21360
    • Kumar, A.1    Wang, Y.2    Lin, X.3    Sun, G.4    Parang, K.5
  • 33
    • 33744829754 scopus 로고    scopus 로고
    • Synthesis and structureactivity relationships of linear and conformationally constrained peptide analogues of CIYKYY as Src tyrosine kinase inhibitors
    • Kumar A, Ye G, Wang Y, Lin X, Sun G, Parang K: Synthesis and structureactivity relationships of linear and conformationally constrained peptide analogues of CIYKYY as Src tyrosine kinase inhibitors. J Med Chem 2006, 49:3395.3401.
    • (2006) J Med Chem , vol.49 , pp. 33953401
    • Kumar, A.1    Ye, G.2    Wang, Y.3    Lin, X.4    Sun, G.5    Parang, K.6
  • 34
    • 6344236775 scopus 로고    scopus 로고
    • ATP-phosphopeptide conjugates as inhibitors of SRC tyrosine kinases
    • Nam NH, Lee S, Ye G, Sun G, Parang K: ATP-phosphopeptide conjugates as inhibitors of Src tyrosine kinases. Bioorg Med Chem 2004, 12:5753.5766.
    • (2004) Bioorg Med Chem , vol.12 , pp. 57535766
    • Nam, N.H.1    Lee, S.2    Ye, G.3    Sun, G.4    Parang, K.5
  • 35
    • 2542528563 scopus 로고    scopus 로고
    • Conformationally constrained peptide analogues of pTyr-Glu-Glu-Ile as inhibitors of the Src SH2 domain binding
    • DOI 10.1021/jm040008+
    • Nam NH, Ye G, Sun G, Parang K: Conformationally constrained peptide analogues of pTyr-Glu-Glu-Ile as inhibitors of the Src SH2 domain binding. J Med Chem 2004, 47:3131-3141. (Pubitemid 38702707)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.12 , pp. 3131-3141
    • Nam, N.-H.1    Ye, G.2    Sun, G.3    Parang, K.4
  • 36
    • 40549094672 scopus 로고    scopus 로고
    • DABCO-catalyzed efficient synthesis of naphthopyran derivatives via one-pot three-component condensation reaction at room temperature
    • DOI 10.1080/00397910701862865, PII 791370440
    • Balalaie S, Ramezanpour S, Bararjanian M, Gross JH: DABCO-catalyzed efficient synthesis of naphthopyran derivatives via One-Pot threecomponent condensation reaction at room temperature. Synthetic Commun 2008, 38:1078-1089. (Pubitemid 351364149)
    • (2008) Synthetic Communications , vol.38 , Issue.7 , pp. 1078-1089
    • Balalaie, S.1    Ramezanpour, S.2    Bararjanian, M.3    Gross, J.H.4
  • 37
    • 34047202588 scopus 로고    scopus 로고
    • Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media
    • DOI 10.1016/j.tetlet.2007.02.135, PII S0040403907004352
    • Abdolmohammadi S, Balalaie S: Novel and efficient catalysts for the onepot synthesis of 3, 4-dihydropyrano[c]chromene derivatives in aqueous media. Tetrahedron Lett 2007, 48:3299-3303. (Pubitemid 46533987)
    • (2007) Tetrahedron Letters , vol.48 , Issue.18 , pp. 3299-3303
    • Abdolmohammadi, S.1    Balalaie, S.2
  • 38
    • 79955583562 scopus 로고    scopus 로고
    • Fatty acyl amide derivatives of doxorubicin: Synthesis and in vitro anticancer activities
    • Chhikara BS, St Jean N, Mandal D, Kumar A, Parang K: Fatty acyl amide derivatives of doxorubicin: synthesis and in vitro anticancer activities. Eur J Med Chem 2011, 46:2037-2042.
    • (2011) Eur J Med Chem , vol.46 , pp. 2037-2042
    • Chhikara, B.S.1    St Jean, N.2    Mandal, D.3    Kumar, A.4    Parang, K.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.