Synthesis and evaluation of A-ring diastereomers of 1alpha,25-dihydroxy-22-oxavitamin D3 (OCT).
A-ring diastereomers of 1alpha,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1alpha,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1alpha,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1alpha,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1alpha,25-dihydroxyvitamin D3 (1).
Hatakeyama
S
S
Faculty of Pharmaceutical Sciences, Nagasaki University, Japan.
Okano
T
T
Maeyama
J
J
Esumi
T
T
Hiyamizu
H
H
Iwabuchi
Y
Y
Nakagawa
K
K
Ozono
K
K
Kawase
A
A
Kubodera
N
N
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000378:metabolism; D002117:Calcitriol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism*; D002417:Cattle; D002454:Cell Differentiation / Q000187:drug effects; D018922:HL-60 Cells; D006801:Humans; D015675:Osteocalcin / Q000187:drug effects / Q000235:genetics; D011485:Protein Binding; D051381:Rats; D018167:Receptors, Calcitriol / Q000378:metabolism; D013237:Stereoisomerism; D013250:Steroid Hydroxylases / Q000187:drug effects / Q000235:genetics; D015533:Transcriptional Activation / Q000187:drug effects; D014809:Vitamin D-Binding Protein / Q000378:metabolism
D000970:Antineoplastic Agents; D018167:Receptors, Calcitriol; D014809:Vitamin D-Binding Protein; D015675:Osteocalcin; D013250:Steroid Hydroxylases; D002117:Calcitriol; C051883:maxacalcitol