Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors Dedicated to the memory of Dr. Christine Radanyi.

European Journal of Medicinal Chemistry

Volumn 83, Issue , 2014, Pages 498-507

  Audisio, Davide ^a   Methy Gonnot, Délphine ^b   Radanyi, Christine ^b   Renoir, Jack Michel ^b,c   Denis, Stéphanie ^b   Sauvage, Félix ^b   Vergnaud Gauduchon, Juliette ^b   Brion, Jean Daniel ^a   Messaoudi, Samir ^a   Alami, Mouad ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b UNIV PARIS SUD   (France)

^c INSTITUT GUSTAVE ROUSSY   (France)

Author keywords

4TCNA; 6BrCaQ; Apoptosis; Cytotoxicity; Hsp90

Indexed keywords

2 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL METHANESULFONIC ACID; 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL NAPHTHALENE 2 SULFONIC ACID; 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL QUINOLINE 2 SULFONIC ACID; 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL THIOPHENE 2 SULFONIC ACID; 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 8 METHYL 2 OXO 6 (PHENYLETHYNYL) 2H CHROMEN 4 YL 4 METHANEBENZENESULFONIC ACID; 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMINO) 6 ETHYNYL 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONIC ACID; 3 [ 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO] 7 METHOXY 6 [( 4 METHOXYPHENYL)ETHYNYL] 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHANEBENZENESULFONIC ACID; 3 [ 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO] 7 METHOXY 8 METHYL 2 OXO 6 [( 3,4,5 TRIMETHOXYPHENYL)ETHYNYL] 2H CHROMEN 4 YL 4 METHYLBENZENESULFONIC ACID; 3 [ 2,2 DIMETHYLCHROMEN 6 CARBOXAMIDO] 7 METHOXY 6 ( 4 METHOXYPHENYL) 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONIC ACID; 6 BROMO 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONIC ACID; 6 [ 3 (DIMETHYLAMINO)PROP 1 YNYL] 3 ( 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONIC ACID; ANTINEOPLASTIC AGENT; COUMARIN DERIVATIVE; ESTROGEN RECEPTOR ALPHA; FULVESTRANT; HEAT SHOCK PROTEIN 90; HEAT SHOCK PROTEIN 90 INHIBITOR; N ( 6 BROMO 4,7 DIMETHOXY 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N ( 6 ETHYNYL 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 4 HYDROXY 7 METHOXY 6 ( 4 METHOXYPHENYL) 8 METHYL 2 OXO 2H CHROMEN 3 YL] 2,2, DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 4 HYDROXY 7 METHOXY 6 [( 4 METHOXYPHENYL)ETHYNYL] 8 METHYL 2 OXO 2H CHROMEN 3 YL] 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 6 (PHENYLETHYNYL) 2H CHROMEN 3 YL] 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 6 [( 3,4,5 TRIMETHOXYPHENYL)ETHYNYL] 2H CHROMEN 3 YL] 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 6 [(TRIMETHYLSILYL)ETHYNYL] 2H CHROMEN 3 YL] 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 6 [ 3 (DIMETHYLAMINO)PROP 1 YNYL] 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 3 YL] 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N [ 7 HYDROXY 8 METHYL 4 ( 2 MORPHOLINOETHYLAMINO) 2 OXO 2H CHROMEN 3 YL] 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; NOVOBIOCIN; NOVOBIOCIN DERIVATIVE; TAMOXIFEN; UNCLASSIFIED DRUG; UNINDEXED DRUG; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 6 ETHYNYL 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 (2,3,4,6 TETRA O ACETYL BETA GLUCOPYRANOS 1 YL) 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL METHANESULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL NA NAPHTHALENE 2 SULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL QUINOLINE 7 SULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL THIOPHENE2 SULFONAT; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 6 ((4 METHOXYPHENYL)ETHYNYL) 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENSULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 6 (4 METHOXYPHENYL) 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 8 METHYL 2 OXO 6 ((3,4,5 TRIMETHOXYPHENYL)ETHYNYL) 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 8 METHYL 2 OXO 6 (PHENYLETHYNYL) 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 6 (3 (DIMETHYLAMINO)PROP 1 YNYL) 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 6 (3 (DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 METHOXY 8 METHYL 2 OXO 6 ((3,4,5 TRIMETHOXYPHENYL)ETHYNYL) 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; 6 BROMO 3 (2,2 DIMETHYLCHROMAN 6 CARBOXAMIDO) 7 HYDROXY 8 METHYL 2 OXO 2H CHROMEN 4 YL 4 METHYLBENZENESULFONATE; N (4 AMINO 7 (2,3,4,6 TETRA O ACETYL BETA GLUCOPYRANOS 1 YL) 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (4 HYDROXY 7 METHOXY 6 ((4 METHOXYPHENYL)ETHYNYL) 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (4 HYDROXY 7 METHOXY 6 (4 METHOXYPHENYL) 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 6 ((3,4,5 TRIMETHOXYPHENYL)ETHYNYL) 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 6 ((TRIMETHYLSILYL)ETHYNYL) 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 6 (PHENYLETHYNYL) 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (6 (3 (DIMETHYLAMINO)PROP 1 YNYL) 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (6 BROMO 4,7 DIMETHOXY 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (6 ETHYNYL 4 HYDROXY 7 METHOXY 8 METHYL 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE; N (7 HYDROXY 8 METHYL 4 (2 MORPHOLINOETHYLAMINO) 2 OXO 2H CHROMEN 3 YL) 2,2 DIMETHYLCHROMAN 6 CARBOXAMIDE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER CELL LINE; CANCER CELL; CELL SURVIVAL; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IC 50; IN VITRO STUDY; MCF 7 CELL LINE; PROTEIN DEGRADATION; PROTEIN DEPLETION; SUBSTITUTION REACTION; ANTAGONISTS AND INHIBITORS; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; CHEMICAL MODIFICATION; DRUG CYTOTOXICITY; DRUG SCREENING;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; HSP90 HEAT-SHOCK PROTEINS; HUMANS; MCF-7 CELLS; NOVOBIOCIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84903693254     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.067     Document Type: Article

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