89266-24-0Relevant academic research and scientific papers
Structural Insight of New Butyrylcholinesterase Inhibitors Based on Benzylbenzofuran Scaffold
Delogu, Giovanna L.,Era, Benedetta,Fais, Antonella,Goyal, Chinmayi,Kumar, Amit,Matos, Maria J.,Pintus, Francesca
, (2022/03/14)
In the present work, we use a merger of computational and biochemical techniques as a rational guideline for structural modification of benzofuran derivatives to find pertinent structural features for the butyrylcholinesterase inhibitory activity and selectivity. Previously, we revealed a series of 2-phenylbenzofuran compounds that displayed a selective inhibitory activity for BChE. Here, in an effort to discover novel selective BChE inhibitors with favorable physicochemical and pharmacokinetic profiles, 2-benzylbenzofurans were designed, synthesized, and evaluated as BChE inhibitors. The 2-phenylbenzofuran scaffold structure is modified by introducing one methylene spacer between the benzofuran core and the 2-phenyl ring with a hydroxyl substituent in the para or meta position. Either position 5 or 7 of the benzofuran scaffold was substituted with a bromine or chlo-rine atom. Further assessment of the selected list of compounds indicated that the substituent’s nature and position determined their activity and selectivity. 5-bromo-2-(4-hydroxybenzyl)benzofuran 9B proved to be the most potent butyrylcholinesterase inhibitor (IC50 = 2.93 μM) of the studied series. Computational studies were carried out to correlate the theoretical and experimental binding affinity of the compounds to the BChE protein.
2-Phenylbenzofuran derivatives as butyrylcholinesterase inhibitors: Synthesis, biological activity and molecular modeling
Delogu, Giovanna L.,Matos, Maria J.,Fanti, Maura,Era, Benedetta,Medda, Rosaria,Pieroni, Enrico,Fais, Antonella,Kumar, Amit,Pintus, Francesca
, p. 2308 - 2313 (2016/04/20)
A series of 2-phenylbenzofurans compounds was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. Among these benzofuran derivatives, compound 16 exhibited the highest BChE inhibition with an IC50 value of 30.3 μM. This compound was found to be a mixed-type inhibitor as determined by kinetic analysis. Moreover, molecular dynamics simulations revealed that compound 16 binds to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE and it displayed the best interaction energy value, in agreement with our experimental data.
NOVEL 1 -BENZYL-4-PIPERIDINAMINES THAT ARE USEFUL IN THE TREATMENT OF COPD AND ASTHMA
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Page/Page column 38, (2010/11/27)
The invention provides 1 -benzyl- 4 -piperidinamines of the general formula (I), processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds are useful in the treatment of respiratory diseses such a
Research on nitro derivatives of biological interest. XXXIII. Synthesis and action on microorganisms of 5-nitrofurylic and 5-nitro thienylic benzofuran derivatives
Guillaumel,Royer,Le Corre,et al.
, p. 431 - 436 (2007/10/02)
Quite a number of benzofurans substituted at the 2-position by a 5-nitrofuryl, 5-nitrothienyl, 5-nitro 2-furyl ethenyl or 5-nitro 2-thienyl ethenyl group were prepared by heterocyclization of 2-acyloxy benzyltriphenylphosphonium bromides derivated from 2-hydroxy benzyl triphenylphosphonium bromides, themselves obtained by action of triphenylphosphine bromhydrate on ortho hydroxylated benzyl alcohols. Besides, several 5-nitro 2-furoyl benzofurans were also obtained by condensation of diversely substituted salicylaldehydes and 2-bromacetyl 5-nitrofuran. Most of these new benzofuran heterocyclic nitro derivatives are deprived of the parasiticidic and antibacterial properties owned by 2-nitro benzofurans.
