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ID: ALA1134959

Journal: Bioorg Med Chem Lett

Title: Synthesis and testing of 2alpha-modified 1alpha,25-dihydroxyvitamin D(3) analogues with a double side chain: marked cell differentiation activity.

Authors: Suhara Y, Kittaka A, Kishimoto S, Calverley MJ, Fujishima T, Saito N, Sugiura T, Waku K, Takayama H.

Abstract: The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D(3) were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity.

CiteXplore: 12392726

DOI: 10.1016/s0960-894x(02)00722-9