Structure-activity relationship in a purine-scaffold compound series with selectivity for the endoplasmic reticulum Hsp90 paralog Grp94

Journal of Medicinal Chemistry

Volumn 58, Issue 9, 2015, Pages 3922-3943

  Patel, Hardik J ^a   Patel, Pallav D ^a,b   Ochiana, Stefan O ^a   Yan, Pengrong ^a   Sun, Weilin ^a   Patel, Maulik R ^a   Shah, Smit K ^a   Tramentozzi, Elisa ^c   Brooks, James ^d   Bolaender, Alexander ^a   Shrestha, Liza ^a   Stephani, Ralph ^b   Finotti, Paola ^c   Leifer, Cynthia ^d   Li, Zihai ^e   Gewirth, Daniel T ^f   Taldone, Tony ^a   Chiosis, Gabriela ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b ST JOHN'S UNIVERSITY   (United States)

^c UNIVERSITY OF PADOVA   (Italy)

^d Department of Obstetrics Gynecology   (United States)

^e MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^f HAUPTMAN WOODWARD MEDICAL RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (PENT 4 YNYL) 8 (2,4,5 TRICHLOROPHENYLTHIO) 3H PURIN 6 AMINE; 3 (PENT 4 YNYL) 8 [2 (TRIFLUOROMETHOXY)PHENYLTHIO] 3H PURIN 6 AMINE; 5 [[6 AMINO 9 (PENT 4 YN 1 Y L) 9H PURIN 8 YL ] THIO] ISOPHTHALONITRILE; 8 (2 CHLOROPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (2 METHOXYPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (2,4 DICHLOROPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (2,4 DIMETHOXYPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (2,4 DIMETHYLPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (2,5 DICHLOROPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (2,5 DIMETHYLPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (3,5 DICHLOROPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (3,5 DIMETHYLPHENYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (MESITYLTHIO) 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 8 (MESITYLTHIO) 9 (PENT 4 YN 1 YL) 9H PURIN 6 AMINE; 8 [(2,6 DICHLOROPYRIDIN 4 YL)THIO] 9 (PENT 4 YN 1 YL) 9H PURIN 6 AMINE; 8 [(3 BROMO 5 CHLOROPHENYL)THIO] 9 (PENT 4 YN 1 YL) 9H PURIN 6 AMINE; 8 [(3,4 DICHLOROPHENYL)THIO] 9 (PENT 4 YN 1 YL) 9H PURIN 6 AMINE; 8 [(3,5 DIBROMOPHENYL)THIO] 9 (PENT 4 YN 1 YL) 9H PURIN 6 AMINE; 8 [(3,5 DICHLOROPHENYL)THIO] 9 (3,3,3 TRIFLUOROPROPYL) 9H PURIN 6 AMINE; 8 [(3,5 DICHLOROPHENYL)THIO] 9 (5,5,5 TRIFLUOROPENTYL) 9H PURIN 6 AMINE; 8 [(3,5 DICHLOROPHENYL)THIO] 9 (HEX 5 YN 1 YL) 9H PURIN 6 AMINE; 8 [2 CHLORO 5 (TRIFLUOROMETHYL)PHENYLTHIO] 3 (PENT 4 YNYL) 3H PURIN 6 AMINE; 9 (BUT 2 YN 1 YL) 8 [(3,5 DICHLOROPHENYL)THIO] 9H PURIN 6 AMINE; 9 (BUT 3 YN 1 YL) 8 [(3,5 DICHLOROPHENYL)THIO] 9H PURIN 6 AMINE; 9 (PENT 4 YN 1 YL) 8 [(2,3,4 TRICHLOROPHENYL)THIO] 9H PURIN 6 AMINE; ANTINEOPLASTIC AGENT; HEAT SHOCK PROTEIN 90 INHIBITOR; PURINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [2 [6 AMINO 3 (PENT 4 YNYL) 3H PURIN 8 YLTHIO]PHENYL]METHANOL; 8-((3,5-DICHLOROPHENYL)THIO)-9-(3-(ISOPROPYLAMINO)PROPYL)-9H-PURIN-6-AMINE; ADENINE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; GLUCOSE REGULATED PROTEIN 94; HEAT SHOCK PROTEIN 90; LIGAND; MEMBRANE PROTEIN; PROTEIN BINDING; SOMATOMEDIN B; TOLL LIKE RECEPTOR 9; TUMOR NECROSIS FACTOR;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ABSORPTION; DRUG CLEARANCE; DRUG SELECTIVITY; ENDOPLASMIC RETICULUM; FEMALE; HYDROGEN BOND; IC50; LIGAND BINDING; MALE; MAXIMUM PLASMA CONCENTRATION; MOLECULAR DOCKING; MOLECULAR MODEL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; ANIMAL; ANTAGONISTS AND INHIBITORS; BINDING SITE; BIOSYNTHESIS; CELL DIFFERENTIATION; CELL LINE; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; METABOLISM; MYOBLAST; NUDE MOUSE; SECRETION (PROCESS); TISSUE DISTRIBUTION; TUMOR CELL LINE;

ADENINE; ALLOSTERIC SITE; ANIMALS; ANTINEOPLASTIC AGENTS; CELL DIFFERENTIATION; CELL LINE; CELL LINE, TUMOR; ENDOPLASMIC RETICULUM; FEMALE; HSP90 HEAT-SHOCK PROTEINS; INSULIN-LIKE GROWTH FACTOR II; LIGANDS; MEMBRANE GLYCOPROTEINS; MICE, NUDE; MOLECULAR DOCKING SIMULATION; MYOBLASTS; PROTEIN BINDING; PURINES; RECEPTOR, ERBB-2; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TOLL-LIKE RECEPTOR 9; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84929315274     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00197     Document Type: Article

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