106910-71-8

Upstream product

• 28144-70-9 anthranilic acid amide 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of sirtinol analogues as class III histone/protein deacetylase (sirtuin) inhibitors

In a search for potent inhibitors of class III histone/protein deacetylases (sirtuins), a series of sirtinol analogues have been synthesized and the degree of inhibition was assessed in vitro using recombinant yeast Sir2, human SIRT1, and human SIRT2 and in vivo with a yeast phenotypic assay. Two analogues, namely, 3- and 4-[(2-hydroxy-1-naphthalenylmethylene)-amino]-N-(1-phenylethyl) benzamide (i.e., m- and p-sirtinol), were 2- to 10-fold more potent than sirtinol against human SIRT1 and SIRT2 enzymes. In yeast in vivo assay, these two small molecules were as potent as sirtinol. Compounds lacking the 2-hydroxy group at the naphthalene moiety or bearing several modifications at the benzene 2′-position of the aniline portion (carbethoxy, carboxy, and cyano) were 1.3-13 times less potent than sirtinol, whereas the 2′-carboxamido analogue was totally inactive. Both (R)- and (S)-sirtinol had similar inhibitory effects on the yeast and human enzymes, demonstrating no enantioselective inhibitory effect.

Sirtuin Inhibiting Compounds

Provided herein are compositions and methods for treating or preventing cancer and autoimmune diseases. Compositions comprise a sirtuin inhibitory compound that decreases the activity of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contact

Influence of bond fixation in benzo-annulated N-salicylideneanilines and their ortho-C(=O)X derivatives (X = CH3, NH2, OCH 3) on tautomeric equilibria in solution

(Chemical Equation Presented) 1H, 13C, and 15N NMR spectra show that an ortho-C(=O)X group present in the molecules of N-salicylideneanthranilamide (X = NH2), methyl N-salicylideneanthranilate (X = OCH3), N-salicylidene-o- aminoacetophenone (X = CH3), and their benzo analogues have only a minor effect on the tautomeric OH/NH-equilibrium in solution. Only two of three possible tautomers were detected Lability of the absent form was proved by theoretical calculations. Calculated energies show that the enolimino form (OH) is less stable than the enaminone (NH) form only for dibenzo-annulated N-salicylideneanilines. The population of each species in the tautomeric mixture was found to be inversely proportional to its energy. Application of the geometry-based aromaticity index HOMA shows that the effectiveness of the π-electron delocalization in different rings in the molecule depends mostly on the position of benzoannulation. Both the NH...O and N...HO hydrogen bonds present in the NH and OH tautomers respectively, increase the aromaticity of the quasirings H-O-C=C-C=N and O=C-C=C-N-H and decrease the aromatic character of the fused benzene ring. These results seem to be reliable when N-salicylideneanilines studied are compared with naphthalene and their benzo-annulated derivatives i.e., phenanthrene, anthracene, and triphenylene. An analysis of the effectiveness of π-electron delocalization confirms that in all cases studied, the OH form is more stable. Although the HOMA values and calculated energies are not a criterion that allows determination of the dominating tautomer, both of these parameters correctly show the effect of changes in the molecular topology on tautomeric preferences.