A novel application of DDQ as electrophile in the Nenitzescu reaction

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 8, 2011, Pages 2666-2674

  Kucklaender, U ^a   Bollig, R ^a   Frank, W ^a   Gratz, A ^a   Jose, J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

3 Amino benzofurans; Azaspiro 4,5 decatrienes; DDQ addition; Nenitzescu reaction; Proteinkinase CK2 inhibition; Quinones; Radicalion pair; Single electron transfer (SET)

Indexed keywords

1 (5 HYDROXY BENZOFURAN 3 YL) 4 METHYL PENT 2 EN 1 ON; 2,3 DICHLORO 5,6 DICYANO BENZOQUINONE; 3 ACETYLAMINO 4 ACETYLAMINOMETHYLEN 5 ACETOXY BENZO[B]FURAN 2 CARBOXYLIC ACID ETHYL ESTER; 3 AMINO 4 AMINOMETHYLEN 5 HYDROXY BENZO[B]FURAN 2 CARBOXYLIC ACID ETHYL ESTER; 3 AMINO 6,7 DICHLORO 4 CYANO 5 ACETOXY BENZO[B]FURAN 2 CARBOXYLIC ACID ETHYL ESTER; 3 AMINO 6,7 DICHLORO 4 CYANO 5 HYDROXY BENZO[B]FURAN 2 CARBOXYLIC ACID ETHYL ESTER; 4 BENZOYL 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 PHENYL 10 OXO 3 PHENYL 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 5 ACETOXY 3 AMINO 6,7 DICHLORO 4 CYANO 2 (3 METHYL BUT 2 ENOYL)BENZO[B]FURAN; 5 ACETOXY 3 AMINO 6,7 DICHLORO 4 CYANO 2 (5 MORPHOLINO 4 YL 5 OXO PENTANOYL)BENZO[B]FURAN; 6 CYANO 7 HYDROXY 1 IMINO 2 (4 BROMOPHENYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 6 CYANO 7 HYDROXY 1 IMINO 2 (4 METHOXYPHENYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 6 CYANO 7 HYDROXY 1 IMINO 2 (4 TOLYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 ACETOXY 1 ACETYLIMINO 2 (2,4 DICHLOROBENZYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 ACETOXY 1 ACETYLIMINO 2 BENZYL 10 OXO 3 PHENYL 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (2,4 DICHLOROBENZYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (2,4 DIFLUOROPHENYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (4 BROMOPHENYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (4 CHLOROPHENYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (4 FLUOROBENZYL) 10 OXO 3 PHENYL 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (4 METHOXYPHENYL) 10 OXO 3 PHENYL 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (4 METHOXYPHENYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 (4 TOLYL) 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 BENZYL 10 OXO 3 PHENYL 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; 8,9 DICHLORO 6 CYANO 7 HYDROXY 1 IMINO 2 ISOBUTYL 3 METHYL 10 OXO 2 AZASPIRO[4.5]DECA 3,6,8 TRIENE 4 CARBOXYLIC ACID ETHYL ESTER; CARBON; CASEIN KINASE II; ELECTROPHILE; OXYGEN; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLIZATION; CYTOSTASIS; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MICHAEL ADDITION; NINETZESCU REACTION; REACTION ANALYSIS;

BENZOFURANS; BENZOQUINONES; CYCLIN-DEPENDENT KINASE 2; CYCLIZATION; CYTOSTATIC AGENTS; HUMANS; ORGANIC CHEMISTRY PROCESSES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79954418106     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.006     Document Type: Article

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