Improved synthesis of EM-1745, preparation of its C17-ketone analogue and comparison of their inhibitory potency on 17β-hydroxysteroid dehydrogenase type 1

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 3, 2009, Pages 832-843

  Bérubé, Marie ^a   Poirier, Donald ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

17 Hydroxysteroid dehydrogenase; Chemical synthesis; Cross metathesis; Enzyme; Inhibitor; Steroid

Indexed keywords

17BETA HYDROXYSTEROID DEHYDROGENASE 1; 5' O [9 [3' (TERT BUTYLDIMETHYLSILYLOXY) 17'BETA (TETRAHYDRO 2H PYRAN 2 YL OXY)ESTRA 1',3',5'(10') TRIEN 16'BETA YL]NONANOYL] 2',3' O ISOPROPYLIDENE ADENOSINE; 5' O [9 [3' HYDROXY 17' OXO ESTRA 1',3',5'(10') TRIEN 16'BETA YL]NONANOYL] 2',3' O ISOPROPYLIDENE ADENOSINE; 5' O [9 [3' HYDROXY 17' OXO ESTRA 1',3',5'(10') TRIEN 16'BETA YL]NONANOYL]ADENOSINE; 5' O [9 [3',17'BETA DIHYDROXY ESTRA 1',3',5'(10') TRIEN 16'BETA YL]NONANOYL] 2',3' O ISOPROPYLIDENE ADENOSINE; 5' O [9 [3',17'BETA DIHYDROXY ESTRA 1',3',5'(10') TRIEN 16'BETA YL]NONANOYL]ADENOSINE; 7 OCTEN 1 OL; 7 OCTENAL; 9 [3' (TERT BUTYLDIMETHYLSILYLOXY) 17'BETA (TETRAHYDRO 2H PYRAN 2 YL OXY)ESTRA 1',3',5'(10') TRIEN 16'BETA YL] 7 NONEN 1 AL; 9 [3' (TERT BUTYLDIMETHYLSILYLOXY) 17'BETA (TETRAHYDRO 2H PYRAN 2 YL OXY)ESTRA 1',3',5'(10') TRIEN 16'BETA YL]NONANOIC ACID; ALCOHOL; EM 1745; ESTRADIOL; KETONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TESTOSTERONE 17BETA DEHYDROGENASE; UNCLASSIFIED DRUG; 3 (OR 17)-BETA-HYDROXYSTEROID DEHYDROGENASE; EM-1745; ENZYME INHIBITOR; HYDROXYSTEROID DEHYDROGENASE; KETONE;

ARTICLE; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HEK293; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME MECHANISM; ESTERIFICATION; HUMAN; HUMAN CELL; HYDROGENATION; IC 50; INFRARED RADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; THIN LAYER CHROMATOGRAPHY; X RAY ANALYSIS; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CELL LINE; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; EMBRYOLOGY; ENZYME SPECIFICITY; KIDNEY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

17-HYDROXYSTEROID DEHYDROGENASES; CELL LINE; ENZYME INHIBITORS; ESTRADIOL; HUMANS; KETONES; KIDNEY; MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 70749099419     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802399761     Document Type: Article

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