203381-39-9Relevant articles and documents
Preparation of aromatic farnesol analogues via a Cu(I)-mediated Grignard coupling of THP ethers
Mechelke, Mark F.,Wiemer, David F.
, p. 783 - 786 (1998)
A Cu(I)-mediated reaction of aromatic Grignard reagents with allylic tetrahydropyranyl ethers results in formation of the coupled products in good yields. This methodology allows facile synthetic manipulation of compounds with two reactive allylic positio
Synthesis of novel vitamin K2 analogues with modification at the Ω-terminal position and their biological evaluation as potent steroid and xenobiotic receptor (SXR) agonists
Suhara, Yoshitomo,Watanabe, Masato,Nakagawa, Kimie,Wada, Akimori,Ito, Yoichi,Takeda, Kazuyoshi,Takahashi, Kazuhiko,Okano, Toshio
supporting information; experimental part, p. 4269 - 4273 (2011/08/22)
Vitamin K2 is a ligand for a nuclear receptor, steroid and xenobiotic receptor (SXR), that induces the gene expressions of CYP3A4. We synthesized vitamin K2 analogues with hydroxyl or phenyl groups at the Ω-terminal of the side chain. The up-regulation of SXR-mediated transcription of the target gene by the analogues was dependent on the length of the side chain and the hydrophobicity of the Ω-terminal residues. Phenyl analogue menaquinone-3 was as active as the known SXR ligand rifampicin.
Synthesis of Farnesol Analogues through Cu(I)-Mediated Displacements of Allylic THP Ethers by Grignard Reagents
Mechelke, Mark F.,Wiemer, David F.
, p. 4821 - 4829 (2007/10/03)
The synthesis of a family of farnesol analogues, incorporating aromatic rings, has been achieved in high yields through the development of a regioselective coupling of allylic tetrahydropyranyl ethers with organometallic reagents. The allylic THP group is displaced readily by Grignard reagents in the presence of Cu(I) halides but is stable in the absence of added copper. Thus, an allylic THP group can fulfill its traditional role as a protecting group or serve as a leaving group depending on reaction conditions. An improved synthesis of (2E,6E)-10,11-dihydrofarnesol also has been accomplished using this methodology, and some preliminary studies on the reactivity and regioselectivity of THP ether displacements were conducted. The farnesol analogues reported herein may be useful probes of the importance of nonbonding interactions in enzymatic recognition of the farnesyl chain and allow development of more potent competitive inhibitors of enzymes such as farnesyl protein transferase.
