(2S,2'R)-analogue of LG190178 is a major active isomer

Wataru Hakamata; Yukiko Sato; Haruhiro Okuda; Shinobu Honzawa; Nozomi Saito; Seishi Kishimoto; Atsushi Yamashita; Takayuki Sugiura; Atsushi Kittaka; Masaaki Kurihara

doi:10.1016/j.bmcl.2007.11.007

(2S,2'R)-analogue of LG190178 is a major active isomer

Bioorg Med Chem Lett. 2008 Jan 1;18(1):120-3. doi: 10.1016/j.bmcl.2007.11.007. Epub 2007 Nov 5.

Authors

Wataru Hakamata¹, Yukiko Sato, Haruhiro Okuda, Shinobu Honzawa, Nozomi Saito, Seishi Kishimoto, Atsushi Yamashita, Takayuki Sugiura, Atsushi Kittaka, Masaaki Kurihara

Affiliation

¹ Division of Organic Chemistry, National Institute of Health Sciences, Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan.

PMID: 18054230
DOI: 10.1016/j.bmcl.2007.11.007

Abstract

Vitamin D receptor (VDR) ligands are therapeutic agents for the treatment of psoriasis, osteoporosis, and secondary hyperparathyroidism. VDR ligands also show immense potential as therapeutic agents for autoimmune diseases and cancers of the skin, prostate, colon, and breast as well as leukemia. LG190178 is a novel non-secosteroidal ligand for VDR. We synthesized and evaluated stereoisomers of LG190178 and found that only an (2S,2'R)-analogue of LG190178 (YR301) had strong activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biphenyl Compounds / chemistry*
Biphenyl Compounds / pharmacology*
Calcitriol / analogs & derivatives*
Calcitriol / chemistry
Calcitriol / metabolism
Drug Design
Ligands
Models, Molecular
Receptors, Calcitriol / chemistry
Receptors, Calcitriol / metabolism*
Stereoisomerism

Substances

Biphenyl Compounds
Ligands
Receptors, Calcitriol
YR301
Calcitriol