Abstract
A series of 1-(1H-benzimidazol-2-yl)-3-substituted phenylprop-2-en-1-ylidene] amino}-1,3,4-thiadiazole-2- thiols (6a-6f) were synthesized by the acid catalyzed nucleophilic addition reaction between 1-(1H-benzimidazol-2-yl)-3- phenylprop-2-en-1-ones (4a-4f) and 5-amino-1,3,4-thiadiazole-2-thiol. All the synthesized compounds were characterised by IR, 1HNMR, 13CNMR, Mass and elemental analyses. A transition state calculation obtained from DFT study to explore the molecular mechanism of action of the synthetic route. The mechanism of synthesis revealed that the imidazole system can make an increase in the electrophilic character of carbonyl carbon in the benzimidazole chalcones. So the electron deficient carbonyl carbon could be efficiently attacked on the amino group of 1,3,4-thiadiazole ring to forms an imine linkage between the two heterocyclic systems. All the titled derivatives at a dose level of 10mg/kg body weight potentiate the hypnotic action of Phenobarbitone (at a dose of 10mg/kg body weight i.p.). The compounds such as 6b, 6a, and 6c showed a significant percentage increase in sleeping time relative to the control experiment 423.8, 387.6 and 329.5 respectively. The preclinical evaluation of the compounds was ascertained by blood-brain barrier, human oral absorption prediction and in silico toxicity assessment.
Keywords: Benzimidazole chalcones, DFT study, imines, hypnotic.
Central Nervous System Agents in Medicinal Chemistry
Title:Hypnotic Profile of Imines from Benzimidazole Chalcones: Mechanism of Synthesis, DFT Studies and in silico Screening
Volume: 13 Issue: 3
Author(s): Bijo Mathew, Jerad Suresh, Sockalingam Anbazhagan and Vinod Devaraji
Affiliation:
Keywords: Benzimidazole chalcones, DFT study, imines, hypnotic.
Abstract: A series of 1-(1H-benzimidazol-2-yl)-3-substituted phenylprop-2-en-1-ylidene] amino}-1,3,4-thiadiazole-2- thiols (6a-6f) were synthesized by the acid catalyzed nucleophilic addition reaction between 1-(1H-benzimidazol-2-yl)-3- phenylprop-2-en-1-ones (4a-4f) and 5-amino-1,3,4-thiadiazole-2-thiol. All the synthesized compounds were characterised by IR, 1HNMR, 13CNMR, Mass and elemental analyses. A transition state calculation obtained from DFT study to explore the molecular mechanism of action of the synthetic route. The mechanism of synthesis revealed that the imidazole system can make an increase in the electrophilic character of carbonyl carbon in the benzimidazole chalcones. So the electron deficient carbonyl carbon could be efficiently attacked on the amino group of 1,3,4-thiadiazole ring to forms an imine linkage between the two heterocyclic systems. All the titled derivatives at a dose level of 10mg/kg body weight potentiate the hypnotic action of Phenobarbitone (at a dose of 10mg/kg body weight i.p.). The compounds such as 6b, 6a, and 6c showed a significant percentage increase in sleeping time relative to the control experiment 423.8, 387.6 and 329.5 respectively. The preclinical evaluation of the compounds was ascertained by blood-brain barrier, human oral absorption prediction and in silico toxicity assessment.
Export Options
About this article
Cite this article as:
Mathew Bijo, Suresh Jerad, Anbazhagan Sockalingam and Devaraji Vinod, Hypnotic Profile of Imines from Benzimidazole Chalcones: Mechanism of Synthesis, DFT Studies and in silico Screening, Central Nervous System Agents in Medicinal Chemistry 2013; 13 (3) . https://dx.doi.org/10.2174/1871524914666140406135930
DOI https://dx.doi.org/10.2174/1871524914666140406135930 |
Print ISSN 1871-5249 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6166 |
- 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
- Announcements
Related Articles
-
Modulation of Cellular Response to Anticancer Treatment by Caffeine: Inhibition of Cell Cycle Checkpoints, DNA Repair and More
Current Pharmaceutical Biotechnology Cancer Resistance to Type II Topoisomerase Inhibitors
Current Medicinal Chemistry Developments of DNA-dependent Protein Kinase Inhibitors as Anticancer Agents
Mini-Reviews in Medicinal Chemistry Anthrax Fusion Protein Therapy of Cancer
Current Protein & Peptide Science Long-term Exposure to Cadmium in Food and Cigarette Smoke, Liver Effects and Hepatocellular Carcinoma
Current Drug Metabolism New Tuberculosis Drugs in Development
Current Topics in Medicinal Chemistry The Management of Membranous Glomerulopathy in Allogeneic Stem Cells Transplantation: Updated Literature
Cardiovascular & Hematological Agents in Medicinal Chemistry Treatment of Chronic Myeloid Leukemia Elderly Patients in the Tyrosine Kinase Inhibitor Era
Current Cancer Drug Targets Chemical and Potential Biological Perspectives of Genus Sarcococca (Buxaceae)
The Natural Products Journal Oxidative Stress in Atherosclerosis Development: The Central Role of LDL and Oxidative Burst
Endocrine, Metabolic & Immune Disorders - Drug Targets Proliferative Activity Of Neokyotorphinrelated Hemoglobin Fragments In Cell Cultures
Protein & Peptide Letters Tissue Protective and Anti-Fibrotic Actions of Suramin: New Uses of an Old Drug
Current Clinical Pharmacology Purinergic Signaling and Energy Homeostasis in Psychiatric Disorders
Current Molecular Medicine Lipoamino Acid Prodrugs of Paclitaxel: Synthesis and Cytotoxicity Evaluation on Human Anaplastic Thyroid Carcinoma Cells
Current Cancer Drug Targets The Small Bowel: An Imaging Guide
Current Medical Imaging Recent Approaches to Improve the Antitumor Efficacy of Temozolomide
Current Medicinal Chemistry Editorial: Looking Forward to Another Successful Year
Current Cancer Drug Targets Overview of Brain Tumor Stem Cells – Implications for Treatment
Current Signal Transduction Therapy Recombinant Adenovirus-mediated Cytotoxic Gene Therapy and Lymphoproliferative Disorders: Analysis Based on Pharmacodynamics
Current Drug Targets - Immune, Endocrine & Metabolic Disorders Transcription Factor NF-κB Inhibitors as Single Therapeutic Agents or in Combination with Classical Chemotherapeutic Agents for the Treatment of Hematologic Malignancies
Current Molecular Pharmacology