Syntheses and biological evaluation of novel 2alpha-substituted 1alpha,25-dihydroxyvitamin D3 analogues.
Novel 2alpha-substituted 1alpha,25-dihydroxyvitamin D3 analogues were efficiently synthesized and their biological activities were evaluated. 2alpha-Methyl-1alpha,25-dihydroxyvitamin D3 (2), whose unique biological activities were previously reported, was modified to 2alpha-alkyl (ethyl and propyl) and 2alpha-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2alpha-Hydroxypropyl-1alpha,25-dihydroxyvitamin D3 (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile.
Suhara
Y
Y
Faculty of Pharaceutical Sciences, Teikyo University, Sagamiko, Kanagawa, Japan.
Nihei
K I
KI
Tanigawa
H
H
Fujishima
T
T
Konno
K
K
Nakagawa
K
K
Okano
T
T
Takayama
H
H
D001671:Biochemistry / Q000379:methods; D002117:Calcitriol / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D002120:Calcium Channel Agonists / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects; D002762:Cholecalciferol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical; D018922:HL-60 Cells / Q000187:drug effects; D006801:Humans; D018167:Receptors, Calcitriol / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014807:Vitamin D / Q000031:analogs & derivatives / Q000737:chemistry; D014809:Vitamin D-Binding Protein / Q000378:metabolism
C413745:2-hydroxypropyl-1,25-dihydroxyvitamin D3; C116441:2-methyl-1,25-dihydroxyvitamin D3; D002120:Calcium Channel Agonists; D018167:Receptors, Calcitriol; D014809:Vitamin D-Binding Protein; D014807:Vitamin D; D002762:Cholecalciferol; D002117:Calcitriol