31604-39-4Relevant articles and documents
π-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)-benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid
Glidewell, Christopher,Low, John N.,Skakle, Janet M.S.,Wardell, James L.
, p. o120-o124 (2004)
Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C 14H10N2O5, are linked into centrosymmetric R22(8) dimers by a single O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.623 (2) A and O-H...O = 178°] and these dimers are linked into sheets by a single aromatic π-π stacking interaction. The isomeric compound 2-(4-nitrophenylamino-carbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P21212 1 with Z′ = 1, crystallized from ethanol), the molecules are linked into sheets of R44(22) rings by a combination of one N-H...O hydrogen bond [H...O = 1.96 A, N...O = 2.833 (3) A and N-H...O = 171°] and one O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.614 (3) A and O-H...O = 173°]. In the monoclinic form (space group P21/n with Z′ = 2, crystallized from acetone), the molecules are linked by a combination of two N-H...O hydrogen bonds [H...O = 2.09 and 2.16 A, N...O = 2.873 (4) and 2.902 (3) A, and N-H...O = 147 and 141°] and two O-H...O hydrogen bonds [H...O = 1.84 and 1.83 A, O...O = 2.664 (3) and 2.666 (3) A, and O-H...O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C-H...O hydrogen bond [H...O = 2.45 A, C...O = 3.355 (4) A and C-H...O = 160°].
Discovery of phthalimide derivatives as novel inhibitors of a soluble epoxide hydrolase
Mahlooji, Iman,Shokri, Maryam,Manoochehri, Rana,Mahboubi-Rabbani, Mohammad,Rezaee, Elham,Tabatabai, Sayyed Abbas
, (2020/06/05)
Soluble epoxide hydrolase (sEH) inhibitors are effective in reducing blood pressure, inflammation, and pain in a number of mammalian disease models. As most classical urea-based sEH inhibitors suffer from poor solubility and pharmacokinetic properties, the development of novel sEH inhibitors with an improved pharmacokinetic specification has received a great deal of attention. In this study, a series of amide-based sEH inhibitors bearing a phthalimide ring as the novel secondary pharmacophore (P2) was designed, synthesized, and evaluated. Docking results illustrated that the amide group as the primary pharmacophore (P1) was placed at a suitable distance from the three key amino acids (Tyr383, Tyr466, and Asp335) for an effective hydrogen bonding. In agreement with these findings, most of the newly synthesized compounds demonstrated moderate?to?high sEH inhibitory activities, relative to 12-(3-adamantan-1-yl-ureido)dodecanoic acid as the reference standard. Compound 12e with a 4-methoxybenzoyl substituent exhibited the highest sEH inhibitory activity, with an IC50 value of 1.06 nM. Moreover, the ADME properties of the compounds were evaluated in silico, and the results revealed appropriate predictions.
Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael
, p. 1898 - 1907 (2019/02/05)
We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.
