Abstract
Condensation of ketones 1a-b with deferent aldehydes 2a-e gives chalcones 3a-j. These chalcones on cyclization with hydrazine hydrate/ phenylhydrazine in the presence of glacial acetic acid give the corresponding pyrazolines 4a-t. The structures of new compounds have been established by extensive IR, NMR and X-ray crystallographic studies and were assayed for their antitubercular activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis strains using agar dilution method. Among the both derivative compounds, 4-hydroxy-3-(5-(4- trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl-2H-chromen-2-one 4m produced the highest efficacy, exhibited >90% inhibition against MTB at a concentration of 4.94 µM and against INHR-MTB at 14.78 µM.
Keywords: Mycobacterium tuberculosis, 3-Acetyl-4-hydroxycoumarins, Chalcones and Pyrazolines.
Letters in Drug Design & Discovery
Title:Synthesis of Novel and Highly Functionalized 4-hydroxycoumarin Chalcone and their Pyrazoline Derivatives as Anti-Tuberculosis Agents
Volume: 11 Issue: 2
Author(s): Mohammad Asad, Farzana Beevi, Suresh Pandian Ganesan, Chuan-Wei Oo, Raju Suresh Kumar, Venu Laxmipathi, Hasnah Osman and Mohamed Ashraf Ali
Affiliation:
Keywords: Mycobacterium tuberculosis, 3-Acetyl-4-hydroxycoumarins, Chalcones and Pyrazolines.
Abstract: Condensation of ketones 1a-b with deferent aldehydes 2a-e gives chalcones 3a-j. These chalcones on cyclization with hydrazine hydrate/ phenylhydrazine in the presence of glacial acetic acid give the corresponding pyrazolines 4a-t. The structures of new compounds have been established by extensive IR, NMR and X-ray crystallographic studies and were assayed for their antitubercular activity against M. tuberculosis H37Rv and INH resistant M. tuberculosis strains using agar dilution method. Among the both derivative compounds, 4-hydroxy-3-(5-(4- trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl-2H-chromen-2-one 4m produced the highest efficacy, exhibited >90% inhibition against MTB at a concentration of 4.94 µM and against INHR-MTB at 14.78 µM.
Export Options
About this article
Cite this article as:
Asad Mohammad, Beevi Farzana, Pandian Ganesan Suresh, Oo Chuan-Wei, Suresh Kumar Raju, Laxmipathi Venu, Osman Hasnah and Ashraf Ali Mohamed, Synthesis of Novel and Highly Functionalized 4-hydroxycoumarin Chalcone and their Pyrazoline Derivatives as Anti-Tuberculosis Agents, Letters in Drug Design & Discovery 2014; 11 (2) . https://dx.doi.org/10.2174/15701808113109990055
DOI https://dx.doi.org/10.2174/15701808113109990055 |
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
-
Editorial [Hot Topic: Fighting Malaria in the 21st Century (Executive Editor: Pedro L. Alonso) ]
Current Molecular Medicine EDITORIAL: New Avenues in Controlling Infectious Diseases
Current Topics in Medicinal Chemistry Recent Patents of Gene Sequences Relative to DNA Polymerases
Recent Patents on DNA & Gene Sequences Anti-cytokines and Cytokines in the Treatment of Rheumatoid Arthritis
Current Pharmaceutical Design Meet the Editorial Board Member
Current Pharmaceutical Biotechnology Design, Synthesis, Pharmacological Evaluation, In silico Modeling, Prediction of Toxicity and Metabolism Studies of Novel 1-(substituted)-2-methyl- 3-(4-oxo-2-phenyl quinazolin-3(4H)-yl)isothioureas
Medicinal Chemistry Proteomic analysis of a <i>hom</i>-disrupted, cephamycin C overproducing <i>Streptomyces clavuligerus</i>
Protein & Peptide Letters The Potential for Genetically Altered Microglia to Influence Glioma Treatment
CNS & Neurological Disorders - Drug Targets Renal & Ocular Targets for Therapy in Wegeners Granulomatosis
Inflammation & Allergy - Drug Targets (Discontinued) The Immunoproteasome as a Therapeutic Target for Hematological Malignancies
Current Cancer Drug Targets Magnetic Materials for the Selective Analysis of Peptide and Protein Biomarkers
Current Medicinal Chemistry Design, Synthesis, Molecular Docking, and Anticancer Evaluation of Pyrazole Linked Pyrazoline Derivatives with Carbothioamide Tail as EGFR Kinase Inhibitors
Anti-Cancer Agents in Medicinal Chemistry New Anti-Tuberculosis Drugs with Novel Mechanisms of Action
Current Medicinal Chemistry Short Antimicrobial Peptides
Recent Patents on Anti-Infective Drug Discovery Synthesis and Molecular Modeling Studies of Novel 2,4-Disubstituted-1, 5-Diphenyl-1-H-Imidazole Derivatives as Potential Anti-Tubercular Agents
Current Bioactive Compounds An Overview on the Potential Antimycobacterial Agents Targeting Serine/Threonine Protein Kinases from Mycobacterium tuberculosis
Current Topics in Medicinal Chemistry Simultaneous And Extended Delivery Of Stavudine, Lamivudine And Nevirapine In Fixed Dose Combination Using Sandwiched Osmotic Tablets For Hiv Therapy
Current Drug Delivery Carbohydrate based Potential Chemotherapeutic Agents: Recent Developments and their Scope in Future Drug Discovery
Mini-Reviews in Medicinal Chemistry Investigation of Potential Inhibitors of Chorismate-Utilizing Enzymes
Current Medicinal Chemistry Glycoconjugates: Roles in Neural Diseases Caused by Exogenous Pathogens
CNS & Neurological Disorders - Drug Targets