Dataset Information

Synthesis of a New Class of Spirooxindole-Benzo[b]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors.

ABSTRACT: A series of new oxindole-based spiro-heterocycles bearing the benzo[b]thiophene motif were synthesized via a 1,3-dipolar cycloaddition reaction and their acetylcholinesterase (AChE) inhibitory activity was evaluated. All the synthesized compounds exhibited moderate inhibitory activities against AChE, while IIc was found to be the most active analog with an IC50 value of 20,840 µM·L-1. Its molecular structure was a 5-chloro-substituted oxindole bearing benzo[b]thiophene and octahydroindole moieties. Based on molecular docking studies, IIc was strongly bound to the catalytic and peripheral anionic sites of the protein through hydrophilic, hydrophobic, and ?-stacking interactions with Asp74, Trp86, Tyr124, Ser125, Glu202, Ser203, Trp236, Trp286, Phe297, Tyr337, and Tyr341. These interactions also indicated that the multiplicity of the IIc aromatic core significantly favored its activity.

SUBMITTER: Barakat A

PROVIDER: S-EPMC7594047 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Synthesis of a New Class of Spirooxindole-Benzo[b]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors.

Barakat Assem A Alshahrani Saeed S Al-Majid Abdullah Mohammed AM Ali M M Altowyan Mezna Saleh MS Islam Mohammad Shahidul MS Alamary Abdullah Saleh AS Ashraf Sajda S Ul-Haq Zaheer Z

Molecules (Basel, Switzerland) 20201013 20

A series of new oxindole-based spiro-heterocycles bearing the benzo[b]thiophene motif were synthesized via a 1,3-dipolar cycloaddition reaction and their acetylcholinesterase (AChE) inhibitory activity was evaluated. All the synthesized compounds exhibited moderate inhibitory activities against AChE, while IIc was found to be the most active analog with an IC50 value of 20,840 µM·L-1. Its molecular structure was a 5-chloro-substituted oxindole bearing benzo[<i ...[more]

PMID: 33066293

Dataset Information

Synthesis of a New Class of Spirooxindole-Benzo[b]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors.

Publications

Synthesis of a New Class of Spirooxindole-Benzo[<i>b</i>]Thiophene-Based Molecules as Acetylcholinesterase Inhibitors.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets

Similar Datasets

Synthesis and biological evaluation of thiophene derivatives as acetylcholinesterase inhibitors.
| S-EPMC6268334 | biostudies-literature

A New Class of Benzo[<i>b</i>]thiophene-chalcones as Cholinesterase Inhibitors: Synthesis, Biological Evaluation, Molecular Docking and ADME Studies.
| S-EPMC11356821 | biostudies-literature

A novel class of selective acetylcholinesterase inhibitors: synthesis and evaluation of (E)-2-(benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles.
| S-EPMC6269038 | biostudies-literature

Design, Synthesis, and Evaluation of Novel 2H-Benzo[b][1,4]thiazin-3(4H)-one Derivatives as New Acetylcholinesterase Inhibitors.
| S-EPMC9000418 | biostudies-literature

Construction of Spirooxindole Analogues Engrafted with Indole and Pyrazole Scaffolds as Acetylcholinesterase Inhibitors.
| S-EPMC8637602 | biostudies-literature

Synthesis, Biological Evaluation, and In Silico Studies of New Acetylcholinesterase Inhibitors Based on Quinoxaline Scaffold.
| S-EPMC8400540 | biostudies-literature

Synthesis and Inhibition Evaluation of New Benzyltetrahydroprotoberberine Alkaloids Designed as Acetylcholinesterase Inhibitors.
| S-EPMC6760013 | biostudies-literature

Structure-Based Design and Synthesis of Piperidinol-Containing Molecules as New Mycobacterium abscessus Inhibitors.
| S-EPMC7083170 | biostudies-literature

Solution-phase parallel synthesis of a multi-substituted benzo[b]thiophene library.
| S-EPMC2743771 | biostudies-literature

Design, Synthesis and Bioactivity Evaluation of Coumarin-BMT Hybrids as New Acetylcholinesterase Inhibitors.
| S-EPMC9000719 | biostudies-literature