114694-09-6Relevant articles and documents
Synthesis of 24,24-dihomo-1α,25-dihydroxyvitamin D3
Tachibana
, p. 2349 - 2351 (1994)
An alternative synthesis of 24,24-dihomo-1α,25-dihydroxyvitamin D3 was achieved starting from stigmasterol or cholenic acid
Parallel synthesis of a vitamin D3 library in the solid-phase
Hijikuro,Doi,Takahashi
, p. 3716 - 3722 (2007/10/03)
A highly efficient synthesis of the vitamin D3 system on solid support is described. Two synthetic strategies for the solid-phase synthesis of vitamin D3 were developed. One is for 11-hydroxy analogues, and the other is for most other synthetic analogues. In the latter strategy, the sulfonate-linked CD-ring 58 was initially immobilized on PS-DES resin to give solid-supported CD-ring 63 (Scheme 10). Similarly, solid-supported CD-ring 63 was prepared by attachment of the CD-ring 10 to the chlorosulfonate resin 64. The vitamin D3 system was synthesized by Horner-Wadsworth-Emmons reaction of the A-ring phosphine oxide to a solid-supported CD-ring, followed by simultaneous introduction of the side chain and cleavage from resin with a Cu1-catalyzed Grignard reagent. Parallel synthesis of the vitamin D3 analogues was accomplished by a split and pool methodology utilizing radio frequency encoded combinatorial chemistry, and a manual parallel synthesizer for side chain diversification and deprotection. Additionally, we demonstrated the synthesis of various A-rings in a similar protocol for efficient preparation of building blocks.
Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol
Chodynski, Michal,Wojciechowska, Wanda,Halkes, Sebastian J.,Van De Velde, Jan-Paul,Kutner, Andrzej
, p. 546 - 553 (2007/10/03)
A synthesis and an in vitro evaluation of side chain-unsaturated analogs 3 and 4 of 24a, 24b-dihomo-1,25-dihydroxycholecalciferol (1) are described. Novel C(23a,24)-vitamin D synthons (sulfone 10 and aldehyde 11) were used for the synthesis of analog 4 and for the efficient preparation of the parent compound 1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane 12 or Wittig reagent 15 for the preparation of compound 1 and analog 4, respectively. Introduction of a 24aE double bond results in a selective, 1000-fold increase in the binding affinity of analog 4 for the vitamin D receptor, compared to the affinity of 1, whereas the affinity of 4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged.
Novel Convergent Synthesis of Side-Chain-Modified Analogues of 1α,25-Dihydroxycholecalciferol and 1α,25-Dihydroxyergocalciferol
Kutner, Andrzej,Perlman, Kato L.,Lago, Amparo,Sicinski, Rafal R.,Schnoes, Heinhrich K.,DeLuca, H. F.
, p. 3450 - 3457 (2007/10/02)
A novel synthetic strategy for the preparation of side-chain-modified analogues of 1α,25-dihydroxycholecalciferol and 1α,25-dihydroxyergocalciferol was developed as a part of the extensive synthetic search for vitamin D analogues of potential anticancer a
