- Asymmetric Dearomative Fluorination of 2-Naphthols with a Dicarboxylate Phase-Transfer Catalyst
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A linked dicarboxylate phase-transfer catalyst enables smooth asymmetric dearomative fluorination of 2-naphthols with Selectfluor under mild conditions to give the corresponding 1-fluoronaphthalenone derivatives in a highly enantioselective manner. This r
- Egami, Hiromichi,Hamashima, Yoshitaka,Masuda, Kousuke,Niwa, Tomoki,Rouno, Taiki,Yamashita, Kenji
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supporting information
p. 14101 - 14105
(2020/06/10)
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- Controlling the C(sp3)-C(sp2) Axial Conformation in the Enantioselective Friedel-Crafts-Type Alkylation of β-Naphthols with Inden-1-ones
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The Friedel-Crafts-type reaction between properly functionalized inden-1-ones and 2-naphthols generates a hindered single bond which displays a unique preference for an antiperiplanar conformational diastereoisomer. The steric hindrance and the presence of an enantioenriched stereogenic center control the distribution of the two diastereomeric conformers at equilibrium and increase the energy for the rotation of the C(sp3)-C(sp2) single bond.
- Di Iorio, Nicola,Filippini, Giacomo,Mazzanti, Andrea,Righi, Paolo,Bencivenni, Giorgio
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supporting information
p. 6692 - 6695
(2017/12/26)
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- ERβ ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERβ selectivity
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The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERβ were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERβ, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.
- Mewshaw, Richard E.,Edsall Jr., Richard J.,Yang, Cuijian,Manas, Eric S.,Xu, Zhang B.,Henderson, Ruth A.,Keith Jr., James C.,Harris, Heather A.
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p. 3953 - 3979
(2007/10/03)
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- Substituted phenyl naphthalenes as estrogenic agents
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This invention provides estrogen receptor modulators of formula I, having the structure 1wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.
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