158365-54-9Relevant articles and documents
Preparation and Binding Affinity of New Porphyrin Host Molecule for Ubiquinone Analogues
Hayashi, Takashi,Miyahara, Takashi,Aoyama, Yasunori,Nonoguchi, Masanori,Ogoshi, Hisanobu
, p. 1749 - 1752 (1994)
αααα-meso-Tetra(7-hydroxy-1-naphthyl)porphyrin (1) is prepared as a host molecule for ubiquinone analogue, 2,3,5,6-tetramethoxy-p-benzoquinone (2).The affinity and thermodynamic aspects in porphyrin 1 - quinone 2 pairing were determined by titrimetric measyrement of electronic absorption and fluorescence spectra.The binding constant of 1 for 2 at 298 K is obtained; Ka = 7.9*102 M-1 in toluene.The fashion of this porphyrin-quinone pairing was large different from that of previous host, αααα-meso-tetra(2-hydroxy-1-naphthyl)porphyrin (3), - quinone 2 pairing.
A facile synthesis of melatonergic antidepressant agomelatine
Kandagatla, Bhaskar,Raju, Vetukuri Venkata Naga Kali Vara Prasada,Reddy, Ganta Madhusudhan,Rao, Sirigiri Chandrakanth,Iqbal, Javed,Bandichhor, Rakeshwar,Oruganti, Srinivas
, p. 7125 - 7127 (2013/01/15)
Agomelatine was synthesized from 8-aminonaphthalen-2-ol by diazotization-iodination, formylation, C-C bond formation by nitroaldol and Pd/C hydrogenation of β-nitrovinylnaphthalene followed by N-acetylation. The route reported employs readily and commercially viable starting materials and reagents, and can potentially be utilized for process synthesis of agomelatine.
ERβ ligands. 3. Exploiting two binding orientations of the 2-phenylnaphthalene scaffold to achieve ERβ selectivity
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.
, p. 3953 - 3979 (2007/10/03)
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.