Catalyst-free synthesis of quinazolin-4-ones from (hetero)aryl-guanidines: Application to the synthesis of pyrazolo[4,3-f]quinazolin-9-ones, a new family of DYRK1A inhibitors

Molecular Diversity

Volumn 16, Issue 4, 2012, Pages 659-667

  Debray, Julien ^a   Bonte, Simon ^a   Lozach, Olivier ^b   Meijer, Laurent ^b   Demeunynck, Martine ^a  

^a Laboratoire de Pharmacochimie   (France)

^b STATION BIOLOGIQUE   (France)

Author keywords

Cyclization; Kinase inhibition; Nitrogen heterocycles; Quinazoline

Indexed keywords

2 HYDROXYETHYLAMINO 3H,4H PYRIDO[3,2 F]QUINAZOLIN 4 ONE; 2 PROPYLAMINO 3H,4H PYRIDO[3,2 H]QUINAZOLIN 4 ONE; 3 (BIPHENYL 4 AMINO) 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 3 ACETYL 7 (2 ACETOXYETHYLAMINO) 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 3 ACETYL 7 PROPARGYLAMINO 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 6 METHOXY 2 PROPYLAMINO 3H,4H QUINAZOLIN 4 ONE; 7 (2 ACETOXYETHYLAMINO) 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 (2 HYDROXYETHYLAMINO) 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 (2 MORPHOLINOETHYLAMINO) 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 (3 HYDROXYPROPYLAMINO) 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 (ADAMANTAN 1 YL)AMINO 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 [4 (DIMETHYLAMINO)PHENYL]AMINO 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 [[2 (PYRIDIN 2 YL)ETHYL]AMINO]] 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 BENZYLAMINO 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 DIALLYLAMINO 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 PROPARGYLAMINO 3H,8H,9H PYRAZOLO[4,3 F]QUINAZOLIN 9 ONE; 7 PROPYLAMINO 2 TRIFLUOROMETHYL 3H,8H,9H IMIDAZO[4,5 F]QUINAZOLIN 9 ONE; GUANIDINE DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; CLK DUAL SPECIFICITY KINASES; CLK DUAL-SPECIFICITY KINASES; DYRK KINASE; ENZYME INHIBITOR; PROTEIN SERINE THREONINE KINASE; PROTEIN TYROSINE KINASE; QUINAZOLINONE DERIVATIVE; RECOMBINANT PROTEIN;

ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; CYCLIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; PRIORITY JOURNAL; STEREOCHEMISTRY; WATER TEMPERATURE; ANIMAL; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; ESCHERICHIA COLI; HEAT; HUMAN; METABOLISM; MOUSE; RAT; SWINE; SYNTHESIS; TRANSITION TEMPERATURE;

ANIMALS; CATALYSIS; CYCLIZATION; DRUG DESIGN; ENZYME INHIBITORS; ESCHERICHIA COLI; GUANIDINES; HOT TEMPERATURE; HUMANS; MICE; MOLECULAR STRUCTURE; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES; QUINAZOLINONES; RATS; RECOMBINANT PROTEINS; SWINE; TRANSITION TEMPERATURE;

EID: 84878042404     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-012-9397-7     Document Type: Article

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