Synthesis and biological characterization of spiro[2H-(1,3)-benzoxazine-2, 4′-piperidine] based histone deacetylase inhibitors

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 273-284

  Thaler, Florian ^a,b   Varasi, Mario ^a,b   Abate, Agnese ^a,b,e   Carenzi, Giacomo ^a,b,f   Colombo, Andrea ^c,g   Bigogno, Chiara ^c,h   Boggio, Roberto ^a,i   Zuffo, Roberto Dal ^a,b   Rapetti, Daniela ^c   Resconi, Anna ^c   Regalia, Nickolas ^c   Vultaggio, Stefania ^a,b   Dondio, Giulio ^c,h   Gagliardi, Stefania ^c   Minucci, Saverio ^b,d   Mercurio, Ciro ^a  

^a Genextra Group   (Italy)

^b EUROPEAN INSTITUTE OF ONCOLOGY   (Italy)

^c NiKem Research   (Italy)

^d UNIVERSITY OF MILAN   (Italy)

^e TEMPLE UNIVERSITY   (United States)

^f Fondazione Istituto Insubrico Ricerca Per la Vita   (Italy)

^g Teva Pharmaceuticals Fine Chemicals   (Italy)

^h Fondazione Istituto Insubrico di Ricerca per la Vita ^*  (Italy)

ⁱ NERVIANO MEDICAL SCIENCES   (Italy)

Author keywords

Antiproliferation; Histone deacetylases; Hydroxamates; In vivo antitumor activity; Pharmacokinetics; Privileged scaffolds

Indexed keywords

3 [1' (2 PHENYLETHYL) 3,4 DIHYDRO 3 BENZYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' (2 PHENYLETHYL) 3,4 DIHYDRO 3 METHYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' (2 PHENYLETHYL) 3,4 DIHYDRO 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' (4 FLUOROBENZYL) 3,4 DIHYDRO 3 BENZYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' (4 FLUOROBENZYL) 3,4 DIHYDRO 3 METHYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' (4 FLUOROBENZYL) 3,4 DIHYDRO 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' BENZYL 3,4 DIHYDRO 3 BENZYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' BENZYL 3,4 DIHYDRO 3 METHYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' METHYL 3,4 DIHYDRO 3 BENZYL 4 OXOSPIRO[2H (1,3) BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [1' METHYL 3,4 DIHYDRO 3 METHYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [10 METHYL 3,4 DIHYDRO 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,40 PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [3,4 DIHYDRO 3 BENZYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [3,4 DIHYDRO 3 METHYL 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3 [3,4 DIHYDRO 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; 3[1' BENZYL 3,4 DIHYDRO 4 OXOSPIRO[2H (1,3)BENZOXAZINE 2,4' PIPERIDIN] 6 YL]N HYDROXYACRYLAMIDE; ANTINEOPLASTIC AGENT; BELINOSTAT; ENTINOSTAT; HISTONE DEACETYLASE 2; HISTONE DEACETYLASE 3; HISTONE DEACETYLASE 6; HISTONE DEACETYLASE INHIBITOR; MOCETINOSTAT; PANOBINOSTAT; PIPERIDINE DERIVATIVE; POTASSIUM CHANNEL HERG; ROMIDEPSIN; UNCLASSIFIED DRUG; VORINOSTAT;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; BINDING AFFINITY; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL CYCLE S PHASE; CELL STRAIN HCT116; CONTROLLED STUDY; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG HALF LIFE; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; LIVER MICROSOME; MAXIMUM PLASMA CONCENTRATION; MOUSE; NEOPLASM; NONHUMAN; TIME TO MAXIMUM PLASMA CONCENTRATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZOXAZINES; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HELA CELLS; HISTONE DEACETYLASE INHIBITORS; HISTONE DEACETYLASES; HUMANS; K562 CELLS; MICE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; NEOPLASMS, EXPERIMENTAL; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877045821     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.061     Document Type: Article

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