72904-78-0Relevant articles and documents
The 2α-(3-hydroxypropyl) group as an active motif in vitamin D3 analogues as agonists of the mutant vitamin D receptor (Arg274Leu)
Honzawa, Shinobu,Yamamoto, Yasuhiro,Yamashita, Atsushi,Sugiura, Takayuki,Kurihara, Masaaki,Arai, Midori A.,Kato, Shigeaki,Kittaka, Atsushi
, p. 3002 - 3024 (2008/09/20)
We designed and synthesized 1α- and 1β-hydroxymethyl-2α-(3-hydroxypropyl)-25-hydroxyvitamin D3 (2a,b) and related analogues 2α-(3-hydroxypropyl)-25-hydroxyvitamin D3 (3), Posner's analogues of 1α- and 1β-hydroxymethyl-25-hydroxyvitamin D3 (4a,b), as well as 2α-(3-hydroxypropyl)-1α,25-dihydroxyvitamin D3 (5), to confirm the effect of the 1α-hydroxy group and/or 2α-(3-hydroxypropyl) group of vitamin D3 analogues with the modified A-ring moiety on the mutant vitamin D receptor, VDR(Arg274Leu). The 2α-(3-hydroxypropyl) group showed better effect on enhancement of the transcriptional activity through the mutant VDR than the 1α- and 1β-hydroxymethyl groups.
Synthesis of 24,24-ethanovitamin D3 lactones using ruthenium-catalyzed intermolecular enyne metathesis: Potent vitamin D receptor antagonists
Saito, Nozomi,Masuda, Manami,Saito, Hiroshi,Takenouchi, Kazuya,Ishizuka, Seiichi,Namekawa, Jun-Ichi,Takimoto-Kamimura, Midori,Kittaka, Atsushi
, p. 2533 - 2543 (2007/10/03)
Novel vitamin D receptor antagonists, 24,24-ethanovitamin D 3-26,23-lactones 6 and 7 and their 2α-functionalized analogues 6a-c and 7a-c were synthesized and their biological activities were evaluated. The triene structure of vitamin D3/s
Enantiomerically pure decalinic structures from carbohydrates using intramolecular Diels-Alder and Ferrier carbocyclization
Taillefumier, Claude,Chapleur, Yves
, p. 708 - 722 (2007/10/03)
The synthesis of enantiomerically pure decalinic structures, advanced intermediates for the synthesis of the hexahvdronaphtalen part of mevinic acids, is described. The key steps are the intramolecular Diels-Alder cycloaddition of a suitably substituted sugar enone obtained via the Ferrier rearrangement of tri-O-acetyl-D-glucal with the appropriate alcohol representing the diene part of the system. Chemical manipulation of the resulting. diastereomerically pure, cycloadduct led to a 5,6-unsaturated carbohydrate which was submitted to the Ferrier carbocylization. This reaction proved difficult likely because of the embedding of the aglycon in a cycle, the hydration product of the double bond being the main product. This compound was in turn transformed into the decalinic structures by treatment in basic medium. The inverse strategy. Ferrier carbocyclization followed by IMDA of an enone and a diene linked via an ester bond was unsuccessful.