Application In Synthesis of Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 2-(1-methyl-1H-pyrrol-2-yl)acetate, is researched, Molecular C8H11NO2, CAS is 51856-79-2, about 3-(4-Aroyl-1-methyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamides as a New Class of Synthetic Histone Deacetylase Inhibitors. 2. Effect of Pyrrole-C2 and/or -C4 Substitutions on Biological Activity. Author is Mai, Antonello; Massa, Silvio; Cerbara, Ilaria; Valente, Sergio; Ragno, Rino; Bottoni, Patrizia; Scatena, Roberto; Loidl, Peter; Brosch, Gerald.
Previous SAR studies performed on some portions (pyrrole-C4, pyrrole-N1, and hydroxamate group) of 3-(4-benzoyl-1-methyl-1H-pyrrol-2-yl)-N-hydroxy-2-propenamide (I) highlighted the I-4-phenylacetyl and I-4-cinnamoyl analogs as more potent compounds in inhibiting maize HD2 activity in vitro. In the present paper, we investigated the effect on anti-HD2 activity of chem. substitutions performed on the pyrrole-C2 ethene chains of I and analogs, which were replaced with methylene, ethylene, substituted ethene, and 1,3-butadiene chains. Biol. results clearly indicated the unsubstituted ethene chain as the best structural motif to get the highest HDAC inhibitory activity, the sole exception to this rule being the introduction of the 1,3-butadienyl moiety into the I chem. structure. IC50 values of compounds prepared as I homologues revealed that between benzene and carbonyl groups at the pyrrole-C4 position a hydrocarbon spacer length ranging from two to five methylenes is well accepted by the APHA template, while the introduction of a higher number of methylene units decreased the inhibitory activities of the derivatives Conformationally constrained forms of I analogs, prepared with the aim to obtain some information potentially useful for a future 3D-QSAR study, showed the same or higher HD2 inhibiting activities in comparison with those of the reference drugs. Mol. modeling and docking calculations on the designed compounds performed in parallel with the chem. work fully supported the synthetic effort and gave insights into the binding mode of the more flexible APHA derivatives
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