Abstract
A series of different Schiff bases of isatin 1-20 was synthesized by the condensation of isatin with primary aromatic amines. It was observed that some of these compounds have the potential to inhibit acetylcholinesterase, whereas some others showed specific activity against butyrylcholinesterase, depending upon substitution on the aromatic ring. Compounds 9 and 20 showed weak acetylcholinesterase inhibitory activity having IC50 values 28.3 ± 0.26 and 159 ± 2.9 μM, respectively. Nonetheless, compounds showed a varying degree of activity against butyrylcholinesterase with IC50 values in the range of 2.8 ± 0.07-82.9 ± 2.2 μM. Compounds 5, 2, and 11 showed IC50 values 2.8 ± 0.07, 5.2 ± 0.10, and 8.1 ± 0.30 μM, respectively, Their activity was compared with standard inhibitor galanthamine IC50 = 0.5 ± 0.01 μM for acetylcholinesterase and IC50 = 8.5 ± 0.01 μM for butyrylcholinesterase, respectively. The structures of all the synthesized compounds were confirmed by spectroscopic analysis.
Keywords: Isatin, Schiff bases, Substitution effect, Butyrylcholinesterase inhibition, Galanthamine, Structure-activity relationship, Acetylcholinestrase inhibition, Butyrylcholinesterase, Gal-anthamine, AChE, senile dementia, Alzheimer's dis-ease, BChE, acetylcholine, indoles, triazoles, spiroheterocy-cle, quinolones, CHN analysis, H-NMR, EI MS, IR, UV spectroscopy, spectrometer, MeOH, Enzyme Inhibition Assay, TLC, EtOH
Letters in Drug Design & Discovery
Title: Schiff Bases of Isatin: Inhibitory Potential Towards Acetylcholinesterase and Butyrylcholinesterase
Volume: 7 Issue: 10
Author(s): Khalid Mohammed Khan, Uzma Rasool Mughal, Nida Ambreen, Nasim Hasan Rama, Farzana Naz, Shahnaz Perveen and Muhammad Iqbal Choudhary
Affiliation:
Keywords: Isatin, Schiff bases, Substitution effect, Butyrylcholinesterase inhibition, Galanthamine, Structure-activity relationship, Acetylcholinestrase inhibition, Butyrylcholinesterase, Gal-anthamine, AChE, senile dementia, Alzheimer's dis-ease, BChE, acetylcholine, indoles, triazoles, spiroheterocy-cle, quinolones, CHN analysis, H-NMR, EI MS, IR, UV spectroscopy, spectrometer, MeOH, Enzyme Inhibition Assay, TLC, EtOH
Abstract: A series of different Schiff bases of isatin 1-20 was synthesized by the condensation of isatin with primary aromatic amines. It was observed that some of these compounds have the potential to inhibit acetylcholinesterase, whereas some others showed specific activity against butyrylcholinesterase, depending upon substitution on the aromatic ring. Compounds 9 and 20 showed weak acetylcholinesterase inhibitory activity having IC50 values 28.3 ± 0.26 and 159 ± 2.9 μM, respectively. Nonetheless, compounds showed a varying degree of activity against butyrylcholinesterase with IC50 values in the range of 2.8 ± 0.07-82.9 ± 2.2 μM. Compounds 5, 2, and 11 showed IC50 values 2.8 ± 0.07, 5.2 ± 0.10, and 8.1 ± 0.30 μM, respectively, Their activity was compared with standard inhibitor galanthamine IC50 = 0.5 ± 0.01 μM for acetylcholinesterase and IC50 = 8.5 ± 0.01 μM for butyrylcholinesterase, respectively. The structures of all the synthesized compounds were confirmed by spectroscopic analysis.
Export Options
About this article
Cite this article as:
Mohammed Khan Khalid, Rasool Mughal Uzma, Ambreen Nida, Hasan Rama Nasim, Naz Farzana, Perveen Shahnaz and Iqbal Choudhary Muhammad, Schiff Bases of Isatin: Inhibitory Potential Towards Acetylcholinesterase and Butyrylcholinesterase, Letters in Drug Design & Discovery 2010; 7 (10) . https://dx.doi.org/10.2174/1570180811007010716
DOI https://dx.doi.org/10.2174/1570180811007010716 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Multi-Constituent Cardiovascular Pills (MCCP) - Challenges and Promises of Population-Based Prophylactic Drug Therapy for Prevention of Heart Attack
Current Pharmaceutical Design An Update on Peptide Drugs for Voltage-Gated Calcium Channels
Recent Patents on CNS Drug Discovery (Discontinued) Editorial: Rediscovering Drug Discovery
Combinatorial Chemistry & High Throughput Screening Use of Diuretics in Women for Management of Hypertension
Current Hypertension Reviews Treatment of Obesity: Should We Target the Individual or Society?
Current Pharmaceutical Design Serotonin – Kynurenine Hypothesis of Depression: Historical Overview and Recent Developments
Current Drug Targets Renin-Angiotensin-Aldosterone System in Autosomal Dominant Polycystic Kidney Disease
Current Hypertension Reviews Impact of Ocular Compatible Lipoids and Castor Oil in Fabrication of Brimonidine Tartrate Nanoemulsions by 3<sup>3</sup> Full Factorial Design
Recent Patents on Inflammation & Allergy Drug Discovery Optimal Sedation for the Ventilation of Critically Ill Patients
Current Respiratory Medicine Reviews Is there a Relationship between Endothelial Dysfunction of the Brachial Artery, Carotid Intima-Media Thickness and Soluble Receptors of Tumor Necrosis Factor-Alpha?
Vascular Disease Prevention (Discontinued) Designing Multi-Targeted Therapeutics for the Treatment of Alzheimer's Disease
Current Topics in Medicinal Chemistry Drug in Adhesive Transdermal Formulation of Valsartan and Nifedipine: Pharmacokinetics and Pharmacodynamics in Rats
Current Drug Therapy Development and Validation of a Sensitive HPLC-MS/MS-ESI Method for Determination of Febuxostat: Application to Pharmacokinetic Study
Current Analytical Chemistry The Cellular Effects of Carbon Monoxide in the Airway
Current Molecular Medicine Alcohol and the Cardiovascular System: A Double-Edged Sword
Current Pharmaceutical Design Cardiac and Muscular Involvement in Idiopathic Inflammatory Myopathies: Noninvasive Diagnostic Assessment and the Role of Cardiovascular and Skeletal Magnetic Resonance Imaging
Inflammation & Allergy - Drug Targets (Discontinued) The Relationship Between Inflammation, Dyslipidemia and Physical Exercise: From the Epidemiological to Molecular Approach
Current Diabetes Reviews An Inflammation-related Nutrient Pattern is Associated with Both Brain and Cognitive Measures in a Multiethnic Elderly Population
Current Alzheimer Research Renovascular Hypertension: Novel Insights
Current Hypertension Reviews Nitrite as a Physiological Source of Nitric Oxide and a Signalling Molecule in the Regulation of the Cardiovascular System in Both Mammalian and Non-Mammalian Vertebrates
Recent Patents on Cardiovascular Drug Discovery