PMID- 25486940
OWN - NLM
STAT- MEDLINE
DCOM- 20150820
LR  - 20190907
IS  - 1873-4294 (Electronic)
IS  - 1568-0266 (Linking)
VI  - 14
IP  - 21
DP  - 2014
TI  - Synthesis and properties of 14-epi-1alpha,25-dihydroxy-19-nortachysterol and its 
      2-substituted derivatives.
PG  - 2454-9
AB  - As the first stable tachysterol analogs, 14-epi-19-nortachysterol and its 
      2-substituted derivatives were synthesized using the Stille coupling reaction 
      between the A-ring precursor (three vinylstannanes) and the CD-ring vinyl 
      trifrate. Among them, the 2-methylidene group was hydrogenated with Wilkinson's 
      catalyst regioselectively to obtain 2alpha- and 2beta-methyl analogs after separation; 
      therefore, five new 14-epi-19- nortachysterols were constructed. All 
      14-epi-19-nortachysterols showed moderate to strong human vitamin D receptor 
      (hVDR) binding affinity except the 2alpha-(3-hydroxypropoxy) substituted analog. 
      X-ray cocrystallographic analysis of the [truncated 
      hVDR]-[2-methyl-14-epi-19-nortachysterol] complex exhibited an unusual binding 
      structure that has not been observed previously.
FAU - Sawada, Daisuke
AU  - Sawada D
FAU - Kittaka, Atsushi
AU  - Kittaka A
AD  - Faculty of Pharmaceutical Sciences, Teikyo University, Kaga, Itabashi-ku, Tokyo 
      173-8605, Japan. akittaka@pharm.teikyo-u.ac.jp.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United Arab Emirates
TA  - Curr Top Med Chem
JT  - Current topics in medicinal chemistry
JID - 101119673
RN  - 0 (14-epi-2alpha-hydroxypropoxy-1alpha,25-dihydroxy-19-nortachysterol)
RN  - 0 (Receptors, Calcitriol)
RN  - 1C6V77QF41 (Cholecalciferol)
SB  - IM
MH  - Cholecalciferol/*analogs & derivatives/chemical synthesis/metabolism
MH  - Crystallography, X-Ray
MH  - Humans
MH  - Models, Molecular
MH  - Molecular Structure
MH  - Protein Binding
MH  - Protein Conformation
MH  - Receptors, Calcitriol/*chemistry/*metabolism
MH  - Stereoisomerism
MH  - Structure-Activity Relationship
EDAT- 2014/12/10 06:00
MHDA- 2015/08/21 06:00
CRDT- 2014/12/10 06:00
PHST- 2014/04/28 00:00 [received]
PHST- 2014/08/02 00:00 [revised]
PHST- 2014/08/19 00:00 [accepted]
PHST- 2014/12/10 06:00 [entrez]
PHST- 2014/12/10 06:00 [pubmed]
PHST- 2015/08/21 06:00 [medline]
AID - CTMC-EPUB-63856 [pii]
AID - 10.2174/1568026615666141208103741 [doi]
PST - ppublish
SO  - Curr Top Med Chem. 2014;14(21):2454-9. doi: 10.2174/1568026615666141208103741.