65923-46-8Relevant academic research and scientific papers
Installation of a chiral side chain to a 2-alkylidene-1-cycloalkan-1-ol unit by using allylic substitution
Feng, Chao,Kobayashi, Yuichi
, p. 6666 - 6676 (2013)
The allylic substitution of optically active exocyclic allylic esters of cyclopentane and cyclohexane with ArMgBr-based copper reagents (Ar = aryl) was examined. ArMgBr/Cu(acac)2 in a 2:1 ratio was an adequate reagent to produce the anti-SN2' products efficiently in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). The Ar groups that were successfully installed include Ph and p-tolyl, those with electron-donating (i.e., p-MeOC6H4) and electron-withdrawing groups (i.e., p-FC6H4), and those with sterically demanding groups (i.e., o-tolyl, o-MeOC6H 4). In an examination of an alkyl reagent, BuMgBr/CuBr·Me 2S in a 2:1 ratio in the presence of ZnI2 afforded the product with high regioselectivity (99a€‰%) and in good yield (91a€‰%). The allylic substitution of exocyclic allylic picolinates (n = 1, 2; R = Ph(CH2)2, iPr, Ph) with a ArCu(acac)MgBr reagent (Ar = Ph, p-tolyl, p-MeOC6H4, p-FC6H4, o-tolyl, o-MeOC6H4) that was derived from a 2:1 ratio of ArMgBr and Cu(acac)2 efficiently afforded the anti-SN2' products in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). Copyright
Synthesis and SAR of 1,2-trans-(1-hydroxy-3-phenylprop-1-yl)cyclopentane carboxamide derivatives, a new class of sodium channel blockers
Ok, Dong,Li, Chunshi,Abbadie, Catherine,Felix, John P.,Fisher, Michael H.,Garcia, Maria L.,Kaczorowski, Gregory J.,Lyons, Kathryn A.,Martin, William J.,Priest, Birgit T.,Smith, McHardy M.,Williams, Brande S.,Wyvratt, Matthew J.,Parsons, William H.
, p. 1358 - 1361 (2007/10/03)
Novel cyclopentane-based 3-phenyl-1-hydroxypropyl compounds were evaluated for inhibitory activity against the peripheral nerve sodium channel Na V1.7 and off-target activity against the cardiac potassium channel hERG. The stereochemistry of the hydroxyl group and substitution on the phenyl rings with either fluorinated O-alkyl or alkyl groups were found to be critical for conferring potency against NaV1.7. A benchmark compound from this series displayed efficacy in rat models of inflammatory and neuropathic pain.
