CYP 17 and CYP 19 Inhibitors. Evaluation of Fluorine Effects on the Inhibiting Activity of Regioselectively Fluorinated 1-(Naphthalen-2-ylmethyl)imidazoles was written by Hartmann, Rolf W.;Palusczak, Anja;Lacan, Fabrice;Ricci, Giacomo;Ruzziconi, Renzo. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2004.SDS of cas: 104197-14-0 This article mentions the following:
Regioselectively fluorinated 1-(naphth-2-ylmethyl)imidazoles 1a-h have been synthesized starting from the corresponding (naphth-2-yl)methanols (2). 2a-d have been obtained by LiAlH4-promoted reduction of fluorinated 1-methyl-2-naphthaldehydes. The latter were easily prepared in fairly good overall yields by ceric ammonium nitrate (CAN)-promoted oxidative addition of the suitable 3-(fluoroaryl)-1-trimethylsilyloxy-1-butenes to Et vinyl ether in methanol followed by cyclization of the resulting acetals in strongly acidic medium in the presence of DDQ. 2e-h were prepared by LiAlH4-promoted reduction of the corresponding fluorinated Me 2-naphthoates. The latter were more profitably obtained by reacting the suitable benzyl bromide with the sodium salt of di-Me 2-(2,2-dimethoxyethyl)malonate in DMF followed by demethoxycarbonylation and acid catalyzed cyclization of the resulting acetals. Compared with the non-fluorinated parent compounds 1i-l, fluorinated 1-(naphth-2-yl)methylimidazoles 1a-h turned out to be potent inhibitors of CYP17 and CYP19 enzymes. The most active inhibitor of CYP17 is 1c, whereas CYP19 is strongly inhibited by 1b, 1e, and 1g. Interestingly, 1g is a potent dual inhibitor also being very active towards CYP19. In the experiment, the researchers used many compounds, for example, 4-Bromo-2,6-difluoroanisole (cas: 104197-14-0SDS of cas: 104197-14-0).
4-Bromo-2,6-difluoroanisole (cas: 104197-14-0) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.SDS of cas: 104197-14-0
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem