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Volumn 22, Issue 5, 2013, Pages 2446-2454

Synthesis, cytotoxic, and DNA binding studies of novel fluorinated condensed pyrano pyrazoles

Author keywords

DBU; Electrochemical; HeLa cells; Intercalation; Knoevenagel condensation; Pyrano 2,3 c pyrazole

Indexed keywords

6 AMINO 1 (3 CHLOROPHENYL) 4 (4 METHOXYPHENYL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (3 CHLOROPHENYL) 4 (4 NITROPHENYL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (3 CHLOROPHENYL) 4 (FURAN 2 YL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (3 CHLOROPHENYL) 4 PHENYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (4 FLUOROPHENYL) 4 (4 METHOXYPHENYL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (4 FLUOROPHENYL) 4 (4 NITROPHENYL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (4 FLUOROPHENYL) 4 (THIOPHEN 2 YL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (4 FLUOROPHENYL) 4 P TOLYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 (4 FLUOROPHENYL) 4 PHENYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 1 PHENYL 4 (THIOPHEN 2 YL) 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 4 (3 METHOXYPHENYL) 1 PHENYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 4 (4 FLUOROPHENYL) 1 PHENYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CARBONITRILE; 6 AMINO 4 (4 NITROPHENYL) 1 PHENYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; 6 AMINO 4 (FURAN 2 YL) 1 PHENYL 3 (TRIFLUOROMETHYL) 1,4 DIHYDROPYRANO[2,3 C]PYRAZOLE 5 CAROBONITRILE; ANTINEOPLASTIC AGENT; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84879690694     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0239-z     Document Type: Article
Times cited : (54)

References (28)
  • 1
    • 0022456486 scopus 로고
    • Metals and DNA: Molecular left-handed complements
    • 3016894 10.1126/science.3016894 1:CAS:528:DyaL28XlsVyqur0%3D
    • Barton JK (1986) Metals and DNA: molecular left-handed complements. Science 233:727-734
    • (1986) Science , vol.233 , pp. 727-734
    • Barton, J.K.1
  • 2
    • 0032102816 scopus 로고    scopus 로고
    • Drug-DNA interactions
    • 9666327 10.1016/S0959-440X(98)80064-X 1:CAS:528:DyaK1cXks1egurg%3D
    • Chaires JB (1998) Drug-DNA interactions. Curr Opin Struct Biol 8:314-320
    • (1998) Curr Opin Struct Biol , vol.8 , pp. 314-320
    • Chaires, J.B.1
  • 3
    • 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
    • 17189698 10.1016/j.bmc.2006.12.001 1:CAS:528:DC%2BD2sXmtVeitQ%3D%3D
    • Chou LC, Huang LJ, Yang JS, Lee FY, Teng CM, Kuo SC (2007) Synthesis of furopyrazole analogs of 1-benzyl-3-(5-hydroxymethyl-2-furyl) indazole (YC-1) as novel anti-leukemia agents. Bioorg Med Chem 15:1732-1735
    • (2007) Bioorg Med Chem , vol.15 , pp. 1732-1735
    • Chou, L.C.1    Huang, L.J.2    Yang, J.S.3    Lee, F.Y.4    Teng, C.M.5    Kuo, S.C.6
  • 4
    • 41149132416 scopus 로고    scopus 로고
    • The condensation of salicylaldehydes and malononitrile revisited: Synthesis of new dimeric chromene derivatives
    • 18271600 10.1021/jo702552f 1:CAS:528:DC%2BD1cXitVamsLk%3D
    • Costa M, Areias F, Abrunhosa L, Venancio A, Proenca F (2008) The condensation of salicylaldehydes and malononitrile revisited: synthesis of new dimeric chromene derivatives. J Org Chem 73:1954-1962
    • (2008) J Org Chem , vol.73 , pp. 1954-1962
    • Costa, M.1    Areias, F.2    Abrunhosa, L.3    Venancio, A.4    Proenca, F.5
  • 5
    • 7044237277 scopus 로고    scopus 로고
    • Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions
    • 10.1016/j.tetlet.2004.09.158 1:CAS:528:DC%2BD2cXovVSns74%3D
    • Devi I, Bhuyan PJ (2004) Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions. Tetrahedron Lett 45:8625-8627
    • (2004) Tetrahedron Lett , vol.45 , pp. 8625-8627
    • Devi, I.1    Bhuyan, P.J.2
  • 6
    • 0027345554 scopus 로고
    • Microbial pyran-2-ones and dihydropyran-2-ones
    • 8451032 10.1039/np9931000071 1:CAS:528:DyaK3sXkvFSrs7w%3D
    • Dickinson JM (1993) Microbial pyran-2-ones and dihydropyran-2-ones. Nat Prod Rep 10:71-98
    • (1993) Nat Prod Rep , vol.10 , pp. 71-98
    • Dickinson, J.M.1
  • 8
    • 80054980238 scopus 로고    scopus 로고
    • Discovery of α, β-and- α, γ-Diamino Acid Scaffolds for the Inhibition of M1 family aminopeptidases
    • 22025387 10.1002/cmdc.201100298 1:CAS:528:DC%2BC3MXhtVWrtL%2FF
    • Gumpena R, Kishor C, Ganji RJ, Addlagatta A (2011) Discovery of α, β-and- α, γ-Diamino Acid Scaffolds for the Inhibition of M1 family aminopeptidases. ChemMedChem 6:1971-1976
    • (2011) ChemMedChem , vol.6 , pp. 1971-1976
    • Gumpena, R.1    Kishor, C.2    Ganji, R.J.3    Addlagatta, A.4
  • 9
    • 32044468685 scopus 로고    scopus 로고
    • Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents
    • 16310361 10.1016/j.bmc.2005.10.053 1:CAS:528:DC%2BD28XhtlKlsLw%3D
    • Holla BS, Mahalinga M, Karthikeyan MS, Akberali PM, Shetty NS (2006) Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. Bioorg Med Chem 14:2040-2047
    • (2006) Bioorg Med Chem , vol.14 , pp. 2040-2047
    • Holla, B.S.1    Mahalinga, M.2    Karthikeyan, M.S.3    Akberali, P.M.4    Shetty, N.S.5
  • 10
    • 0036519363 scopus 로고    scopus 로고
    • DNA and its associated processes as targets for cancer therapy
    • 11990855 10.1038/nrc749 1:CAS:528:DC%2BD38Xis1KktL0%3D
    • Hurley LH (2002) DNA and its associated processes as targets for cancer therapy. Nat Rev Cancer 2:188-200
    • (2002) Nat Rev Cancer , vol.2 , pp. 188-200
    • Hurley, L.H.1
  • 11
    • 13944265524 scopus 로고    scopus 로고
    • A clean and simple synthesis of 6-amino- 4-aryl-5-cyano-3-methyl-1- phenyl-1,4-dihydropyrano[2,3-c]pyrazole in water
    • 10.1081/SCC-200046527 1:CAS:528:DC%2BD2MXit1Sksbw%3D
    • Jin TS, Wang AQ, Cheng ZL, Zhang JS, Li TS (2005) A clean and simple synthesis of 6-amino- 4-aryl-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c] pyrazole in water. Synth Commun 35:137-143
    • (2005) Synth Commun , vol.35 , pp. 137-143
    • Jin, T.S.1    Wang, A.Q.2    Cheng, Z.L.3    Zhang, J.S.4    Li, T.S.5
  • 12
    • 0038737165 scopus 로고    scopus 로고
    • Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield
    • 10.1016/S0040-4020(03)00554-4 1:CAS:528:DC%2BD3sXjsVGltrg%3D
    • Kaupp G, Naimi-Jamal MR, Schmeyers J (2003) Solvent-free Knoevenagel condensations and Michael additions in the solid state and in the melt with quantitative yield. Tetrahedron 59:3753-3760
    • (2003) Tetrahedron , vol.59 , pp. 3753-3760
    • Kaupp, G.1    Naimi-Jamal, M.R.2    Schmeyers, J.3
  • 13
    • 77955917668 scopus 로고    scopus 로고
    • DBU: A highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3- b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium
    • 10.1016/j.tet.2010.05.082 1:CAS:528:DC%2BC3cXpt1eqtrg%3D
    • Khurana JM, Nand B, Saluja P (2010) DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano[3,2-c]chromenes, dihydropyrano[4,3- b]pyranes, 2-amino-4H-benzo[h]chromenes and 2-amino-4H benzo[g]chromenes in aqueous medium. Tetrahedron 66:5637-5641
    • (2010) Tetrahedron , vol.66 , pp. 5637-5641
    • Khurana, J.M.1    Nand, B.2    Saluja, P.3
  • 14
    • 11244286166 scopus 로고    scopus 로고
    • 3 under ultrasound irradiation
    • 10.1081/SCC-200043233 1:CAS:528:DC%2BD2cXhtVyisb3F
    • 3 under ultrasound irradiation. Synth Commun 34:4565-4571
    • (2004) Synth Commun , vol.34 , pp. 4565-4571
    • Li, J.T.1    Xu, W.Z.2    Yang, L.C.3    Li, T.S.4
  • 15
    • 33751506561 scopus 로고    scopus 로고
    • Synthesis and anti-tumor activities of novel pyrazolo[1,5-a]pyrimidines
    • 10.1002/ardp.200600098 1:CAS:528:DC%2BD28XhtlSisLvI
    • Li J, Zhao YF, Zhao XL, Yuan XY, Gong P (2006) Synthesis and anti-tumor activities of novel pyrazolo[1,5-a]pyrimidines. Arch Pharm Chem Life Sci 339:593-597
    • (2006) Arch Pharm Chem Life Sci , vol.339 , pp. 593-597
    • Li, J.1    Zhao, Y.F.2    Zhao, X.L.3    Yuan, X.Y.4    Gong, P.5
  • 16
    • 0036387086 scopus 로고    scopus 로고
    • Reduction of azides to amines or amides with zinc and ammonium chloride as reducing agent
    • 10.1081/SCC-120014032 1:CAS:528:DC%2BD38XnvVGgsr0%3D
    • Lin W, Zhang X, He Z, Jin Y, Gong L, Mi A (2002) Reduction of azides to amines or amides with zinc and ammonium chloride as reducing agent. Synth Commun 32:3279-3284
    • (2002) Synth Commun , vol.32 , pp. 3279-3284
    • Lin, W.1    Zhang, X.2    He, Z.3    Jin, Y.4    Gong, L.5    Mi, A.6
  • 18
    • 0036890401 scopus 로고    scopus 로고
    • Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines
    • 12443764 10.1016/S0960-894X(02)00824-7 1:CAS:528:DC%2BD38Xoslyrs7c%3D
    • Marrison LR, Dickinson JM, Fair lamb IJS (2002) Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines. Bioorg Med Chem Lett 12:3509-3523
    • (2002) Bioorg Med Chem Lett , vol.12 , pp. 3509-3523
    • Marrison, L.R.1    Dickinson, J.M.2    Fair Lamb, I.J.S.3
  • 19
    • 77957831524 scopus 로고    scopus 로고
    • Structure activity relationship studies of imidazo[1,2-a]pyrazine derivatives against cancer cell lines
    • 20832916 10.1016/j.ejmech.2010.08.035 1:CAS:528:DC%2BC3cXht1KrtrbI
    • Myadaraboina S, Alla M, Saddanapu V, Bommena VR, Addlagatta A (2010) Structure activity relationship studies of imidazo[1,2-a]pyrazine derivatives against cancer cell lines. Eur J Med Chem 45:5208-5216
    • (2010) Eur J Med Chem , vol.45 , pp. 5208-5216
    • Myadaraboina, S.1    Alla, M.2    Saddanapu, V.3    Bommena, V.R.4    Addlagatta, A.5
  • 20
    • 0034951136 scopus 로고    scopus 로고
    • DNA minor-groove recognition by small molecules
    • 11476483 10.1039/a705982e 1:CAS:528:DC%2BD3MXkslyisbw%3D
    • Neidle S (2001) DNA minor-groove recognition by small molecules. Nat Prod Rep 18:291-309
    • (2001) Nat Prod Rep , vol.18 , pp. 291-309
    • Neidle, S.1
  • 21
    • 0028972032 scopus 로고
    • NMR-titrations with complexes between ds-DNA and indole derivatives including tryptophane containing peptides
    • 7589577 10.1016/0014-5793(95)01158-B 1:CAS:528:DyaK2MXptlCmtbc%3D
    • Sartorius J, Schneider H-J (1995) NMR-titrations with complexes between ds-DNA and indole derivatives including tryptophane containing peptides. FEBS Lett 374:387-392
    • (1995) FEBS Lett , vol.374 , pp. 387-392
    • Sartorius, J.1    Schneider, H.-J.2
  • 22
    • 16044365071 scopus 로고    scopus 로고
    • A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles
    • 10.1016/0040-4020(96)00879-4 1:CAS:528:DyaK28XmslyjtL8%3D
    • Singh K, Singh J, Singh H (1996) A synthetic entry into fused pyran derivatives through carbon transfer reactions of 1,3-oxazinanes and oxazolidines with carbon nucleophiles. Tetrahedron 52:14273-14280
    • (1996) Tetrahedron , vol.52 , pp. 14273-14280
    • Singh, K.1    Singh, J.2    Singh, H.3
  • 23
    • 4644346774 scopus 로고    scopus 로고
    • A clean one-pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media
    • Tong-Shou J, Ai-Qing W, Xin W, Jian-She Z, Tong-Shuang L (2004) A clean one-pot synthesis of tetrahydrobenzo[b]pyran derivatives catalyzed by hexadecyltrimethyl ammonium bromide in aqueous media. Synlett 871-873
    • (2004) Synlett , pp. 871-873
    • Tong-Shou, J.1    Ai-Qing, W.2    Xin, W.3    Jian-She, Z.4    Tong-Shuang, L.5
  • 24
    • 0036325393 scopus 로고    scopus 로고
    • A convenient synthesis of 2-amino-5,6,7,8- tetrahydro-5-oxo-4-aryl-7,7- dimethyl-4H-benzo[b]pyran-3-carbonitrile under microwave irradiation
    • 10.1081/SCC-120005420 1:CAS:528:DC%2BD38XlvFKnu7s%3D
    • Tu SJ, Gao Y, Guo C, Shi DQ, Lu ZS (2002) A convenient synthesis of 2-amino-5,6,7,8- tetrahydro-5-oxo-4-aryl-7,7-dimethyl-4H-benzo[b]pyran-3- carbonitrile under microwave irradiation. Synth Commun 32(14):2137-2141
    • (2002) Synth Commun , vol.32 , Issue.14 , pp. 2137-2141
    • Tu, S.J.1    Gao, Y.2    Guo, C.3    Shi, D.Q.4    Lu, Z.S.5
  • 25
    • 0035977674 scopus 로고    scopus 로고
    • In situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes
    • 11246748 10.1016/S0301-4622(00)00217-9 1:CAS:528:DC%2BD3MXpt12itQ%3D%3D
    • Wang Z, Liu D, Dong S (2001) In situ FTIR study on adsorption and oxidation of native and thermally denatured calf thymus DNA at glassy carbon electrodes. Biophys Chem 89:87-94
    • (2001) Biophys Chem , vol.89 , pp. 87-94
    • Wang, Z.1    Liu, D.2    Dong, S.3
  • 26
    • 0037275890 scopus 로고    scopus 로고
    • A convenient synthesis of 5-Oxo-5,6,7,8-tetrahydro-4 H -benzo-[b]-pyran derivatives catalyzed by KF-Alumina
    • 10.1081/SCC-120015567 1:CAS:528:DC%2BD3sXht1antr0%3D
    • Wang XS, Shi DQ, Tu SJ, Yao CS (2003) A convenient synthesis of 5-Oxo-5,6,7,8-tetrahydro-4 H -benzo-[b]-pyran derivatives catalyzed by KF-Alumina. Synth Commun 33:119-126
    • (2003) Synth Commun , vol.33 , pp. 119-126
    • Wang, X.S.1    Shi, D.Q.2    Tu, S.J.3    Yao, C.S.4
  • 27
    • 0030927763 scopus 로고    scopus 로고
    • Targeting the minor groove of DNA
    • 9204277 10.1016/S0959-440X(97)80051-6 1:CAS:528:DyaK2sXjvFSqtb0%3D
    • Wemmer DE, Dervan PB (1997) Targeting the minor groove of DNA. Curr Opin Struct Biol 7:355-361
    • (1997) Curr Opin Struct Biol , vol.7 , pp. 355-361
    • Wemmer, D.E.1    Dervan, P.B.2
  • 28
    • 33845350344 scopus 로고    scopus 로고
    • Synthesis and anti- HIV evaluation of the novel 2-(m-chlorobenzyl)-4- substituted-7-methyl-1, 1, 3- trioxo- pyrazolo[4, 5-e] [1, 2, 4]thiadiazines
    • 10.1007/BF02969278 1:CAS:528:DC%2BD2sXptFU%3D
    • Yan RZ, Liu XY, Xu WF, Pannecouque C, Witvrouw M, De Clercq E (2006) Synthesis and anti- HIV evaluation of the novel 2-(m-chlorobenzyl)-4- substituted-7-methyl-1, 1, 3- trioxo- pyrazolo[4, 5-e] [1, 2, 4]thiadiazines. Arch Pharmacol Res 29:957-962
    • (2006) Arch Pharmacol Res , vol.29 , pp. 957-962
    • Yan, R.Z.1    Liu, X.Y.2    Xu, W.F.3    Pannecouque, C.4    Witvrouw, M.5    De Clercq, E.6


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