PMID- 27629592
OWN - NLM
STAT- MEDLINE
DCOM- 20171106
LR  - 20171208
IS  - 1879-1220 (Electronic)
IS  - 0960-0760 (Linking)
VI  - 173
DP  - 2017 Oct
TI  - Synthesis of 2alpha- and 2beta-(3-hydroxypropyl)- 
      7,8-cis-14-epi-1alpha,25-dihydroxy-19-norvitamin D(3) and their biological activity.
PG  - 79-82
LID - S0960-0760(16)30243-6 [pii]
LID - 10.1016/j.jsbmb.2016.09.007 [doi]
AB  - According to the binding mode of 14-epi-1alpha,25-dihydroxy-19-nortachysterol in the 
      ligand binding domain of human vitamin D receptor (hVDR), i.e., 5,6- and 
      7,8-s-trans configuration that was shown by X-ray co-crystallographic analysis, 
      7,8-cis-locked 1alpha,25(OH)(2)D(3) analogs were synthesized. In this paper, the 
      synthesis and biological activity of 2alpha- and 
      2beta-(3-hydroxypropyl)-7,8-cis-14-epi-1alpha,25-dihydroxy-19-norvitamin D(3) are 
      reported. The A-ring and CD-ring precursors for the Julia-Kociensky coupling 
      reaction to create a diene system of the target molecules were prepared using our 
      original methods. hVDR binding affinity and osteocalcin promoter transactivation 
      activity of the new 7,8-cis-14-epi-vitamin D(3) analogs were evaluated. 
      Interestingly, the 2beta-substituted 7,8-cis-analog was a better binder for hVDR 
      than the 2alpha-isomeric counterpart.
CI  - Copyright (c) 2016 Elsevier Ltd. All rights reserved.
FAU - Sawada, Daisuke
AU  - Sawada D
AD  - Faculty of Pharmaceutical Sciences, Teikyo University, 2-11-1 Kaga, Itabashi, 
      Tokyo 173-8605, Japan.
FAU - Ochiai, Eiji
AU  - Ochiai E
AD  - Teijin Institute for Bio-medical Research, Teijin Pharma Ltd., 4-3-2 Hino, Tokyo 
      191-8512, Japan.
FAU - Takeuchi, Akiko
AU  - Takeuchi A
AD  - Teijin Institute for Bio-medical Research, Teijin Pharma Ltd., 4-3-2 Hino, Tokyo 
      191-8512, Japan.
FAU - Kakuda, Shinji
AU  - Kakuda S
AD  - Teijin Institute for Bio-medical Research, Teijin Pharma Ltd., 4-3-2 Hino, Tokyo 
      191-8512, Japan.
FAU - Kamimura-Takimoto, Midori
AU  - Kamimura-Takimoto M
AD  - Teijin Institute for Bio-medical Research, Teijin Pharma Ltd., 4-3-2 Hino, Tokyo 
      191-8512, Japan.
FAU - Kawagoe, Fumihiro
AU  - Kawagoe F
AD  - Faculty of Pharmaceutical Sciences, Teikyo University, 2-11-1 Kaga, Itabashi, 
      Tokyo 173-8605, Japan.
FAU - Kittaka, Atsushi
AU  - Kittaka A
AD  - Faculty of Pharmaceutical Sciences, Teikyo University, 2-11-1 Kaga, Itabashi, 
      Tokyo 173-8605, Japan. Electronic address: akittaka@pharm.teikyo-u.ac.jp.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20160911
PL  - England
TA  - J Steroid Biochem Mol Biol
JT  - The Journal of steroid biochemistry and molecular biology
JID - 9015483
RN  - 0 (Receptors, Calcitriol)
RN  - 0 (VDR protein, human)
RN  - 0 (Vitamins)
RN  - 130447-37-9 (1,25-dihydroxy-19-norvitamin D3)
RN  - FXC9231JVH (Calcitriol)
SB  - IM
MH  - Calcitriol/*analogs & derivatives/chemical synthesis/chemistry/pharmacology
MH  - Chemistry Techniques, Synthetic/methods
MH  - Humans
MH  - Protein Binding
MH  - Receptors, Calcitriol/*metabolism
MH  - Vitamins/*chemical synthesis/chemistry/*pharmacology
OTO - NOTNLM
OT  - 7,8-cis-19-norvitamin D(3) analog
OT  - Synthesis
OT  - Transactivation
OT  - VDR binding affinity
OT  - Vitamin D receptor
EDAT- 2016/09/16 06:00
MHDA- 2017/11/07 06:00
CRDT- 2016/09/16 06:00
PHST- 2016/05/24 00:00 [received]
PHST- 2016/08/10 00:00 [revised]
PHST- 2016/09/10 00:00 [accepted]
PHST- 2016/09/16 06:00 [pubmed]
PHST- 2017/11/07 06:00 [medline]
PHST- 2016/09/16 06:00 [entrez]
AID - S0960-0760(16)30243-6 [pii]
AID - 10.1016/j.jsbmb.2016.09.007 [doi]
PST - ppublish
SO  - J Steroid Biochem Mol Biol. 2017 Oct;173:79-82. doi: 10.1016/j.jsbmb.2016.09.007. 
      Epub 2016 Sep 11.