13,13-Dimethyl-des-C,D analogues of (20S)-1α,25-dihydroxy-2- methylene-19-norvitamin D 3 (2MD): Total synthesis, docking to the VDR, and biological evaluation

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 23, 2011, Pages 7205-7220

  Plonska Ocypa, Katarzyna ^a,b   Sibilska, Izabela ^a,b   Sicinski, Rafal R ^a,b   Sicinska, Wanda ^c   Plum, Lori A ^a   Deluca, Hector F ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WARSAW   (Poland)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

19 Norvitamin D; Calcemic activity; Des C,D steroids; Molecular modeling; Vitamin D analogues; Vitamin D receptor

Indexed keywords

1,9 BIS[(TERT BUTYLDIMETHYLSILYL)OXY] 3,3,5,9 TETRAMETHYLDECANE; 1ALPHA,25 DIHYDROXY 2 METHYLENE 19 NORVITAMIN D3; 1ALPHA,25 DIHYDROXY 2 METHYLENE 8(12),14(17) DISECO 9,11,15,16,19 PENTANORVITAMIN D3; 3,5 BIS[(TERT BUTYLDIMETHYLSILYL)OXY] 4 METHYLENECYCLOHEXANONE; 3,5 BIS[(TERT BUTYLDIPHENYLSILYL)OXY] 4 METHYLENECYCLOHEXANONE; 3,5 BIS[2' (TRIMETHYLSILYL)ETHOXYMETHOXY] 4 METHYLENECYCLOHEXANONE; 7 [(TERT BUTYLDIMETHYLSILYL)OXY] 1,4 DIOXASPIRO[4,5]DECAN 8 ONE; 7 [(TERT BUTYLDIMETHYLSILYL)OXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECANE; 7 [(TERT BUTYLDIPHENYLSILYL)OXY] 1,4 DIOXASPIRO[4,5]DECAN 8 ONE; 7 [(TERT BUTYLDIPHENYLSILYL)OXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECANE; 7 [2' (TRIMETHYLSILYL)ETHOXYMETHOXY] 1,4 DIOXASPIRO[4,5]DECAN 8 ONE; 7 HYDROXY 1,4 DIOXASPIRO[4,5]DECAN 8 ONE; 7,9 BIS[(TERT BUTYLDIMETHYLSILYL)OXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECANE; 7,9 BIS[(TERT BUTYLDIPHENYLSILYL)OXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECANE; 7,9 BIS[2' (TRIMETHYLSILYL)ETHOXYMETHOXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECANE; 8 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 [2' [(TERT BUTYLDIMETHYLSILYL)OXY]ETHYL] 2,4,8 TRIMETHYLNONANOIC ACID METHYL ESTER; 8 METHYLENE 7 [2' (TRIMETHYLSILYL)ETHOXYMETHOXY] 1,4 DIOXASPIRO[4,5]DECAN 7 OL DERIVATIVE; 8 METHYLENE 7 [2' (TRIMETHYLSILYL)ETHOXYMETHOXY] 1,4 DIOXASPIRO[4,5]DECANE; 9 [(TERT BUTYLDIMETHYLSILYL)OXY] 3,3,5,9 TETRAMETHYLDECAN 1 OL; 9 [(TERT BUTYLDIMETHYLSILYL)OXY] 3,3,5,9 TETRAMETHYLDECANAL; 9 [(TERT BUTYLDIMETHYLSILYL)OXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECAN 7 OL DERIVATIVE; 9 [(TERT BUTYLDIPHENYLSILYL)OXY] 8 METHYLENE 1,4 DIOXASPIRO[4,5]DECAN 7 OL DERIVATIVE; COLECALCIFEROL DERIVATIVE; HYDROXYL GROUP; PROLINE; PYRIDINE 1 OXIDE; REAGENT; SELENIUM OXIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VITAMIN D RECEPTOR;

ALPHA AMINOXYLATION; ARTICLE; BIOLOGICAL ACTIVITY; CALCIUM TRANSPORT; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONTROLLED STUDY; DEOXYGENATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROLYSIS; HYDROXYLATION; IN VITRO STUDY; ISOMER; METHYLATION; MOLECULAR DOCKING; OXIDATION; RECEPTOR AFFINITY; SCANNING ELECTRON MICROSCOPY; STRUCTURE ACTIVITY RELATION; WITTIG HORNER COUPLING;

ANIMALS; CALCITRIOL; CELL DIFFERENTIATION; CRYSTALLOGRAPHY, X-RAY; HL-60 CELLS; HUMANS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; RATS; RECEPTORS, CALCITRIOL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80655146801     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.09.048     Document Type: Article

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