17509-54-5Relevant academic research and scientific papers
Discovery of adamantane ethers as inhibitors of 11β-HSD-1: Synthesis and biological evaluation
Patel, Jyoti R.,Shuai, Qi,Dinges, Jurgen,Winn, Marty,Pliushchev, Marina,Fung, Steven,Monzon, Katina,Chiou, William,Wang, Jiahong,Pan, Liping,Wagaw, Seble,Engstrom, Kenneth,Kerdesky, Francis A.,Longenecker, Kenton,Judge, Russell,Qin, Wenying,Imade, Hovis M.,Stolarik, DeAnne,Beno, David W.A.,Brune, Michael,Chovan, Linda E.,Sham, Hing L.,Jacobson, Peer,Link
, p. 750 - 755 (2007)
A novel class of adamantane ethers 11β-hydroxysteroid hydrogenase type I inhibitors has been discovered. These compounds have excellent HSD-1 potency and selectivity against HSD-2. The structure-activity relationships, selectivity, metabolism, PK, ex vivo
The formation of benzoxacin-3-ones: Via intramolecular Nicholas reactions and synthesis of 8-membered heliannuols
Green, James R.,St. Onge, Brent
supporting information, p. 7152 - 7155 (2021/08/30)
The γ-carbonyl cations generated from propargyl ether-Co2(CO)6 complexes undergo intramolecular Nicholas reactions to give dehydrobenzoxacin-3-one-Co2(CO)6 complexes in good yields. Reductive decomplexation and subsequent manipulation allows the synthesis of (±)-heliannuol K methyl ether and the formal syntheses of (±)-heliannuol K, (±)-heliannuol A, and (-)-heliannuol L.
Pd(II)-catalyzed ortho - Or meta-C-H olefination of phenol derivatives
Dai, Hui-Xiong,Li, Gang,Zhang, Xing-Guo,Stepan, Antonia F.,Yu, Jin-Quan
supporting information, p. 7567 - 7571 (2013/06/27)
A combination of weakly coordinating auxiliaries and ligand acceleration allows for the development of both ortho- and meta-selective C-H olefination of phenol derivatives. These reactions demonstrate the feasibility of directing C-H functionalizations when functional groups are distal to target C-H bonds. The meta-C-H functionalization of electron-rich phenol derivatives is unprecedented and orthogonal to previous electrophilic substitution of phenols in terms of regioselectivity. These methods are also applied to functionalize α-phenoxyacetic acids, a fibrate class of drug scaffolds.
Liquid-phase synthesis of 2-methyl-2-aryloxypropanoic acid derivatives from poly(ethylene glycol) supported 2-bromo-2-methylpropanoate
Huang, Bin,Huang, Pei-Gang,Sheng, Shou-Ri,Wang, Qiu-Ying,Guo, Lei,Jiang, Shao-Hua
, p. 575 - 578 (2008/02/11)
An efficient liquid-phase synthesis of 2-methyl-2-aryloxypropanoic acid derivatives with good yields and high purity on soluble polyethylene glycol (PEG) has been developed by treatment of PEG-bound 2-bromo-2-methylpropanoate with phenoxides in the presence of a catalytic amount of NBu4I and KI, and subsequent cleavage from the PEG.
Improved method for the synthesis of 2-methyl-2-aryloxypropanoic acid derivatives
Davis, Roman D.,Fitzgerald, Russ N.,Guo, Jiasheng
, p. 1959 - 1962 (2007/10/03)
An improved method for the formation of 2-methyl-2-aryloxypropanoic acid derivatives, an important class of compounds for the potential treatment of type II diabetes, is reported. This method offers several advantages over the existing chemistry for this transformation.
Electrochemically-induced spirolactonization of α-(methoxyphenoxy)alkanoic acids into quinone ketals
Deffieux, Denis,Fabre, Isabelle,Courseille, Christian,Quideau, Stephane
, p. 4458 - 4465 (2007/10/03)
Anodic oxidation of two series of α-(2)- and α-(4-methoxyphenoxy)alkanoic acids were studied both at the analytical and preparative scales in order to delineate mechanistic aspects of electrochemically induced spirolactonization and to develop synthetically useful orthoquinone bis- and monoketals. Although α-monomethylated carboxylic acids and acetic acid derivatives do not undergo any spiroannulation, α-dimethylated carboxylic acids furnished spirolactones in high yields. A gem-dimethyl effect is invoked to explain these differences in cyclization capacity. Electrooxidation conditions can be selected to furnish either quinone spirolactone bis- or monoketals. Chemoselective monohydrolysis of bisketals can also be accomplished in a stepwise fashion to furnish the corresponding spirolactone monoketals, but the ortho compound unfortunately dimerized in situ via a Diels-Alder process. An ECEC pathway is proposed to rationalize the observed spirolactonizations on the basis of cyclic voltammetry analyses.
