메뉴 건너뛰기




Volumn 66, Issue , 2013, Pages 466-479

Synthesis and anticancer activity of 2,4-disubstituted furo[3,2-b] indole derivatives

Author keywords

A498 renal cancer cells; Anticancer activity; Furo 3,2 b indole derivatives; Structure activity relationships (SARs)

Indexed keywords

2,4 DISUBSTITUTED FURO[3,2 B]INDOLE DERIVATIVE; 4 BENZYL 4H FURO[3,2 B]INDOLE 2 CARBOXYLIC ACID; 4 ETHYL 4H FURO[3,2 B]INDOLE 2 CARBOXYLIC ACID; 4 METHYL 4H FURO[3,2 B]INDOLE 2 CARBOXYLIC ACID; 4 METHYL 4H FURO[3,2 B]INDOLE 2 METHANOL; 4H FURO[3,2 B]INDOLE 2 CARBOXYLIC ACID; 4H FURO[3,2 B]INDOLE 2 METHANOL; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; LIFICIGUAT; METHYL 4 (2 CHLOROBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (2 FLUOROBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (2 METHOXYBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (3 CHLOROBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (3 FLUOROBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (3 METHOXYBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (4 CHLOROBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (4 FLUOROBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 (4 METHOXYBENZYL) 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 BENZYL 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 ETHYL 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 METHYL 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 [3 (METHOXYCARBONYL)BENZYL] 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 [3,4 (METHYLENEDIOXY)BENZYL] 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 [4 (METHOXYCARBONYL)BENZYL] 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 [[5 (METHOXYCARBONYL)FURAN 2 YL]METHYL] 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 [[5 (METHOXYCARBONYL)SELENOPHEN 2 YL]METHYL] 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; METHYL 4 [[5 (METHOXYCARBONYL)THIOPHEN 2 YL]METHYL] 4H FURO[3,2 B]INDOLE 2 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [5 [[2 (HYDROXYMETHYL) 4H FURO[3,2 B]INDOL 4 YL]METHYL]FURAN 2 YL]METHANOL; 4 BENZYL 4H FURO[3,2 B]INDOLE 2 METHANOL; 4 ETHYL 4H FURO[3,2 B]INDOLE 2 METHANOL; [5 [(2 (HYDROXYMETHYL) 4H FURO[3,2 B]INDOL 4 YL]METHYL] FURAN 2 YL] METHANOL;

EID: 84879810917     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.06.012     Document Type: Article
Times cited : (40)

References (29)
  • 1
    • 0038771261 scopus 로고    scopus 로고
    • YC-1 inhibits proliferation of human vascular endothelial cells through a cyclic GMP-independent pathway
    • H.K. Hsu, S.H. Juan, P.Y. Ho, Y.C. Liang, C.H. Lin, C.M. Teng, W.S. Lee, YC-1 inhibits proliferation of human vascular endothelial cells through a cyclic GMP-independent pathway, Biochem. Pharmacol. 66 (2003) 263-271.
    • (2003) Biochem. Pharmacol. , vol.66 , pp. 263-271
    • Hsu, H.K.1    Juan, S.H.2    Ho, P.Y.3    Liang, Y.C.4    Lin, C.H.5    Teng, C.M.6    Lee, W.S.7
  • 2
    • 23044433522 scopus 로고    scopus 로고
    • YC-1 [3-(5′-Hydroxymethyl-2′-furyl) -1-benzyl indazole] inhibits endothelial cell functions induced by angiogenic factors in vitro and angiogenesis in vivo models
    • S.L. Pan, J.H. Guh, C.Y. Peng, S.W. Wang, Y.L. Chang, F.C. Cheng, J.H. Chang, S.C. Kuo, F.Y. Lee, C.M. Teng, YC-1 [3-(5′-Hydroxymethyl-2′- furyl) -1-benzyl indazole] inhibits endothelial cell functions induced by angiogenic factors in vitro and angiogenesis in vivo models, J. Pharmacol. Exp. Ther. 314 (2005) 35-42.
    • (2005) J. Pharmacol. Exp. Ther. , vol.314 , pp. 35-42
    • Pan, S.L.1    Guh, J.H.2    Peng, C.Y.3    Wang, S.W.4    Chang, Y.L.5    Cheng, F.C.6    Chang, J.H.7    Kuo, S.C.8    Lee, F.Y.9    Teng, C.M.10
  • 3
    • 18844366701 scopus 로고    scopus 로고
    • A potential role of YC-1 on the inhibition of cytokine release in peripheral blood mononuclear leukocytes and endotoxemic mouse models
    • S.L. Pan, J.H. Guh, C.Y. Peng, Y.L. Chang, F.C. Cheng, J.H. Chang, S.C. Kuo, F.Y. Lee, C.M. Teng, A potential role of YC-1 on the inhibition of cytokine release in peripheral blood mononuclear leukocytes and endotoxemic mouse models, Thromb. Haemost. 93 (2005) 940-948.
    • (2005) Thromb. Haemost. , vol.93 , pp. 940-948
    • Pan, S.L.1    Guh, J.H.2    Peng, C.Y.3    Chang, Y.L.4    Cheng, F.C.5    Chang, J.H.6    Kuo, S.C.7    Lee, F.Y.8    Teng, C.M.9
  • 4
    • 14344254896 scopus 로고    scopus 로고
    • YC-1 [3-(5′-Hydroxymethyl-2′-furyl)-1-benzyl indazole] exhibits a novel antiproliferative effect and arrests the cell cycle in G0-G1 in human hepatocellular carcinoma cells
    • S.W. Wang, S.L. Pan, J.H. Guh, H.L. Chen, D.M. Huang, Y.L. Chang, S.C. Kuo, F.Y. Lee, C.M. Teng, YC-1 [3-(5′-Hydroxymethyl-2′-furyl)-1- benzyl indazole] exhibits a novel antiproliferative effect and arrests the cell cycle in G0-G1 in human hepatocellular carcinoma cells, J. Pharmacol. Exp. Ther. 312 (2005) 917-925.
    • (2005) J. Pharmacol. Exp. Ther. , vol.312 , pp. 917-925
    • Wang, S.W.1    Pan, S.L.2    Guh, J.H.3    Chen, H.L.4    Huang, D.M.5    Chang, Y.L.6    Kuo, S.C.7    Lee, F.Y.8    Teng, C.M.9
  • 5
    • 27644518437 scopus 로고    scopus 로고
    • YC-1 suppresses constitutive nuclear factor-κB activation and induces apoptosis in human prostate cancer cells
    • Y.T. Huang, S.L. Pan, J.H. Guh, Y.L. Chang, F.Y. Lee, S.C. Kuo, C.M. Teng, YC-1 suppresses constitutive nuclear factor-κB activation and induces apoptosis in human prostate cancer cells, Mol. Cancer Ther. 4 (2005) 1628-1635.
    • (2005) Mol. Cancer Ther. , vol.4 , pp. 1628-1635
    • Huang, Y.T.1    Pan, S.L.2    Guh, J.H.3    Chang, Y.L.4    Lee, F.Y.5    Kuo, S.C.6    Teng, C.M.7
  • 6
    • 29244492264 scopus 로고    scopus 로고
    • YC-1 [3-(5′-Hydroxymethyl-2′-furyl)-1-benzyl indazole] inhibits neointima formation in balloon-injured rat carotid through suppression of expressions and activities of matrix metalloproteinases 2 and 9
    • Y.N. Liu, S.L. Pan, C.Y. Peng, J.H. Guh, D.M. Huang, Y.L. Chang, C.H. Lin, H.C. Pai, S.C. Kuo, F.Y. Lee, C.M. Teng, YC-1 [3-(5′-Hydroxymethyl- 2′-furyl)-1-benzyl indazole] inhibits neointima formation in balloon-injured rat carotid through suppression of expressions and activities of matrix metalloproteinases 2 and 9, J. Pharmacol. Exp. Ther. 316 (2006) 35-41.
    • (2006) J. Pharmacol. Exp. Ther. , vol.316 , pp. 35-41
    • Liu, Y.N.1    Pan, S.L.2    Peng, C.Y.3    Guh, J.H.4    Huang, D.M.5    Chang, Y.L.6    Lin, C.H.7    Pai, H.C.8    Kuo, S.C.9    Lee, F.Y.10    Teng, C.M.11
  • 8
    • 84872768240 scopus 로고    scopus 로고
    • YC-1 exerts inhibitory effects on MDA-MB-468 breast cancer cells by targeting EGFR in vitro and in vivo under normoxic condition
    • Y. Cheng, W. Li, Y. Liu, H.C. Cheng, J. Ma, L. Qiu, YC-1 exerts inhibitory effects on MDA-MB-468 breast cancer cells by targeting EGFR in vitro and in vivo under normoxic condition, Chin. J. Cancer 31 (2012) 248-256.
    • (2012) Chin. J. Cancer , vol.31 , pp. 248-256
    • Cheng, Y.1    Li, W.2    Liu, Y.3    Cheng, H.C.4    Ma, J.5    Qiu, L.6
  • 9
    • 33847789058 scopus 로고    scopus 로고
    • Synthesis of furopyrazole analogs of 1-benzyl-3-(5-hydroxymethyl-2-furyl) indazole (YC-1) as novel anti-leukemia agents
    • L.C. Chou, L.J. Huang, J.S. Yang, F.Y. Lee, C.M. Tengc, S.C. Kuo, Synthesis of furopyrazole analogs of 1-benzyl-3-(5-hydroxymethyl-2-furyl) indazole (YC-1) as novel anti-leukemia agents, Bioorg. Med. Chem. 15 (2007) 1732-1740.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 1732-1740
    • Chou, L.C.1    Huang, L.J.2    Yang, J.S.3    Lee, F.Y.4    Tengc, C.M.5    Kuo, S.C.6
  • 10
    • 0004313902 scopus 로고    scopus 로고
    • 1-(Substituted benzyl)-3-(substituted aryl)-condensed pyrazole derivatives and processed of making the same
    • U.S. Patent 5574168
    • S.C. Kuo, F.Y. Lee, C.M. Teng, 1-(Substituted benzyl)-3-(substituted aryl)-condensed pyrazole derivatives and processed of making the same, U.S. Patent 5574168, 1996.
    • (1996)
    • Kuo, S.C.1    Lee, F.Y.2    Teng, C.M.3
  • 12
    • 0021675752 scopus 로고
    • Furo [3, 2-b] indole derivatives. I. Synthesis and analgesic and anti-in flammatory activities of 4, 6-disubstituted-furo [3,2-b] indole-2-carboxamide derivatives
    • Y. Nakashima, Y. Kawashima, F. Amanuma, K. Sota, A. Tanaka, T. Kameyama, Furo [3, 2-b] indole derivatives. I. Synthesis and analgesic and anti-in flammatory activities of 4, 6-disubstituted-furo [3,2-b] indole-2-carboxamide derivatives, Chem. Pharm. Bull. 32 (1984) 4271-4280.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 4271-4280
    • Nakashima, Y.1    Kawashima, Y.2    Amanuma, F.3    Sota, K.4    Tanaka, A.5    Kameyama, T.6
  • 13
    • 0001173379 scopus 로고
    • Oxidation of 2,4-alkadienoic esters with selenium dioxide. A new synthesis of furan and selenophenes
    • S. Tsuboi, S. Minura, S.I. Ono, K. Watanabe, A. Takeda, Oxidation of 2,4-alkadienoic esters with selenium dioxide. A new synthesis of furan and selenophenes, Bull. Chem. Soc. Jpn. 60 (1987) 1807-1812.
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 1807-1812
    • Tsuboi, S.1    Minura, S.2    Ono, S.I.3    Watanabe, K.4    Takeda, A.5
  • 16
    • 0027270211 scopus 로고
    • Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2- yl)-2,5-diphenyltetrazolium bromide (MTT): Subcellular localization, substrate dependence, and involvement of mitochondrial electron transport in MTT reduction
    • DOI 10.1006/abbi.1993.1311
    • M.V. Berridge, A.S. Tan, Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT): subcellular localization, substrate dependence, and involvement of mitochondrial electron transport in MTT reduction, Arch. Biochem. Biophys. 303 (1993) 474-482. (Pubitemid 23199849)
    • (1993) Archives of Biochemistry and Biophysics , vol.303 , Issue.2 , pp. 474-482
    • Berridge, M.V.1    Tan, A.S.2
  • 17
    • 0021365851 scopus 로고
    • Development of the superoxide-generating system during differentiation of the HL-60 human promyelocytic leukemia cell line
    • P.E. Newburger, C. Speier, N. Borregaard, C.E. Walsh, J.C. Whitin, E.R. Simons, Development of the superoxide-generating system during differentiation of the HL-60 human promyelocytic leukemia cell line, J. Biol. Chem. 259 (1984) 3771-3776. (Pubitemid 14173417)
    • (1984) Journal of Biological Chemistry , vol.259 , Issue.6 , pp. 3771-3776
    • Newburger, P.E.1    Speier, C.2    Borregaard, N.3
  • 19
    • 0024354304 scopus 로고
    • Determination of subcutaneous tumor size in athymic (nude) mice
    • DOI 10.1007/BF00300234
    • M.M. Tomayko, C.P. Reynolds, Determination of subcutaneous tumor size in athymic (nude) mice, Cancer Chemother. Pharmacol. 24 (1989) 148-154. (Pubitemid 19163397)
    • (1989) Cancer Chemotherapy and Pharmacology , vol.24 , Issue.3 , pp. 148-154
    • Tomayko, M.M.1    Reynolds, C.P.2
  • 21
    • 0035097161 scopus 로고    scopus 로고
    • Phase II study of 4-Ipomeanol, a naturally occurring alkylating furan, in patients with advanced hepatocellular carcinoma
    • DOI 10.1023/A:1006408803734
    • S. Lakhanpal, R.C. Donehower, E.K. Rowinsky, Phase II study of 4-Ipomeanol, a naturally occurring alkylating furan, in patients with advanced hepatocellular carcinoma, Invest. New Drugs 19 (2001) 69-76. (Pubitemid 32209786)
    • (2001) Investigational New Drugs , vol.19 , Issue.1 , pp. 69-76
    • Lakhanpal, S.1    Donehower, R.C.2    Rowinsky, E.K.3
  • 24
    • 0014603509 scopus 로고
    • Biochemical effects of mithramycin on cultured cells
    • G. Northrop, S.G. Taylor III, R.I. Northrop, Biochemical effects of mithramycin on cultured cells, Cancer Res. 29 (1969) 1916-1919.
    • (1969) Cancer Res. , vol.29 , pp. 1916-1919
    • Northrop, G.1    Taylor III, S.G.2    Northrop, R.I.3
  • 25
    • 80054809459 scopus 로고    scopus 로고
    • Phase I pharmacokinetic and pharmacodynamic study of triciribine phosphate monohydrate, a small-molecule inhibitor of AKT phosphorylation, in adult subjects with solid tumors containing activated AKT
    • C.R. Garrett, D. Coppola, R.M. Wenham, C.L. Cubitt, A.M. Neuger, T.J. Frost, R.M. Lush, D.M. Sullivan, J.Q. Cheng, S.M. Sebti, Phase I pharmacokinetic and pharmacodynamic study of triciribine phosphate monohydrate, a small-molecule inhibitor of AKT phosphorylation, in adult subjects with solid tumors containing activated AKT, Invest. New Drugs 29 (2011) 1381-1389.
    • (2011) Invest. New Drugs , vol.29 , pp. 1381-1389
    • Garrett, C.R.1    Coppola, D.2    Wenham, R.M.3    Cubitt, C.L.4    Neuger, A.M.5    Frost, T.J.6    Lush, R.M.7    Sullivan, D.M.8    Cheng, J.Q.9    Sebti, S.M.10
  • 26
    • 0024444317 scopus 로고
    • Mechanistic aspects of DNA damage by morpholinyl and cyanomorpholinyl anthracyclines
    • J. Westendorf, M. Aydin, G. Groth, O. Weller, H. Marquardt, Mechanistic aspects of DNA damage by morpholinyl and cyanomorpholinyl anthracyclines, Cancer Res. 49 (1989) 5262-5266. (Pubitemid 19240458)
    • (1989) Cancer Research , vol.49 , Issue.19 , pp. 5262-5266
    • Westendorf, J.1    Aydin, M.2    Groth, G.3    Weller, O.4    Marquardt, H.5
  • 27
    • 0030827993 scopus 로고    scopus 로고
    • Aclacinomycin A stabilizes topoisomerase I covalent complexes
    • J.L. Nitiss, P. Pourquier, Y. Pommier, Aclacinomycin A stabilizes topoisomerase I covalent complexes, Cancer Res. 57 (1997) 4564-4569. (Pubitemid 27441062)
    • (1997) Cancer Research , vol.57 , Issue.20 , pp. 4564-4569
    • Nitiss, J.L.1    Pourquier, P.2    Pommier, Y.3
  • 28
    • 0034327355 scopus 로고    scopus 로고
    • Chloroquinoxaline sulfonamide (NSC 339004) is a topoisomerase IIa/b poison
    • H. Gao, E.F. Yamasaki, K.K. Chan, L.L. Shen, R.M. Snapka, Chloroquinoxaline sulfonamide (NSC 339004) is a topoisomerase IIa/b poison, Cancer Res. 60 (2000) 5937-5940.
    • (2000) Cancer Res. , vol.60 , pp. 5937-5940
    • Gao, H.1    Yamasaki, E.F.2    Chan, K.K.3    Shen, L.L.4    Snapka, R.M.5
  • 29
    • 1242297824 scopus 로고    scopus 로고
    • Echinomycin inhibits chromosomal DNA replication and embryonic development in vertebrates
    • DOI 10.1093/nar/gkh166
    • L.G. May, M.A. Madine, M.J. Waring, Echinomycin inhibits chromosomal DNA replication and embryonic development in vertebrates, Nucleic Acids Res. 32 (2004) 65-72. (Pubitemid 38228605)
    • (2004) Nucleic Acids Research , vol.32 , Issue.1 , pp. 65-72
    • May, L.G.1    Madine, M.A.2    Waring, M.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.