Abstract
N-substituted 3-amino-5-hydroxy-4-phenyl-1H-pyrazole-1-carboxamide derivatives have been prepared by heterocyclization of 1-cyanophenyl acetic acid hydrazide with isocyanates. Representative compounds were evaluated as potential antimicrobial agents. The most promising compound in this series, the N-(1-naphthyl)-3-amino-5-hydroxy-4- phenyl-1H-pyrazole-1-carboxamide 2f, was the most effective against the reference strains of pathogenic S. aureus ATCC 25923 and S. aureus ATCC 6538 or opportunistic S. epidermidis ATCC 12228 with MIC value of 7.81 μg/ml and against the other Gram-positive species with MIC values 15.63-31.25 μg/ml. This compound also showed high activity against clinical isolates of MSSA (methicillin-sensitive Staphylococcus aureus) with MIC of 0.98 - 31.25 μg/ml and MRSA (methicillin- resistant Staphylococcus aureus) with MIC of 1.96 – 7.81 μg/ml.
Keywords: Antibacterial activity, pyrazole, synthesis, X-ray analysis, N-substituted, 3-amino, 5-hydroxy, 1H-pyrazole, 1-carboxamide derivatives
Medicinal Chemistry
Title: Synthesis, Structure and Antibacterial Evaluation of Some N-substituted 3-amino-5-hydroxy-4-phenyl-1H-pyrazole-1-carboxamides
Volume: 7 Issue: 6
Author(s): Monika Pitucha, Urszula Kosikowska, Liliana Urszula and Anna Malm
Affiliation:
Keywords: Antibacterial activity, pyrazole, synthesis, X-ray analysis, N-substituted, 3-amino, 5-hydroxy, 1H-pyrazole, 1-carboxamide derivatives
Abstract: N-substituted 3-amino-5-hydroxy-4-phenyl-1H-pyrazole-1-carboxamide derivatives have been prepared by heterocyclization of 1-cyanophenyl acetic acid hydrazide with isocyanates. Representative compounds were evaluated as potential antimicrobial agents. The most promising compound in this series, the N-(1-naphthyl)-3-amino-5-hydroxy-4- phenyl-1H-pyrazole-1-carboxamide 2f, was the most effective against the reference strains of pathogenic S. aureus ATCC 25923 and S. aureus ATCC 6538 or opportunistic S. epidermidis ATCC 12228 with MIC value of 7.81 μg/ml and against the other Gram-positive species with MIC values 15.63-31.25 μg/ml. This compound also showed high activity against clinical isolates of MSSA (methicillin-sensitive Staphylococcus aureus) with MIC of 0.98 - 31.25 μg/ml and MRSA (methicillin- resistant Staphylococcus aureus) with MIC of 1.96 – 7.81 μg/ml.
Export Options
About this article
Cite this article as:
Pitucha Monika, Kosikowska Urszula, Urszula Liliana and Malm Anna, Synthesis, Structure and Antibacterial Evaluation of Some N-substituted 3-amino-5-hydroxy-4-phenyl-1H-pyrazole-1-carboxamides, Medicinal Chemistry 2011; 7 (6) . https://dx.doi.org/10.2174/157340611797928433
DOI https://dx.doi.org/10.2174/157340611797928433 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
Call for Papers in Thematic Issues
Carbohydrates in Computational and Medicinal Chemistry
Carbohydrates are the most essential organic molecules and are involved in the maintenance of various physiological and metabolic processes in living organisms. Carbohydrate-based compounds have come to the attention of researchers because of their significant contributions to biological functions, such as cell development and cell proliferation, connections between several cells, ...read more
Recent Advances in the Medicinal Chemistry of Cancer
Scope of the Thematic Issue: Correlation between structure and function is one of the important aspects of the success of anti-cancer compounds associated with their structure-activity interactions, physiology, biochemical, molecular, and genetic processes. Overcoming these obstacles is key to obtaining further insights into developments in rational drug design, bioorganic chemistry, ...read more
- 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
-
Drug-Induced Thromboembolic Events in Patients with Malignancy
Cardiovascular & Hematological Disorders-Drug Targets Triple-Valve Endocarditis in a Diabetic Patient: Case Report and Literature Review
Current Cardiology Reviews Lantibiotic Production by Pathogenic Microorganisms
Current Protein & Peptide Science Role of Natural Product in Modulation of Drug Transporters and New Delhi Metallo-β Lactamases
Current Topics in Medicinal Chemistry Therapeutic Modulation of Gut Microbiota: Current Clinical Applications and Future Perspectives
Current Drug Targets Methadone and the Heart: What the Clinician Needs to Know
Current Drug Abuse Reviews Glycoprotein Targeting and Other Applications of Lectins in Biotechnology
Current Protein & Peptide Science Inflammatory Syndrome in Chronic Kidney Disease: Pathogenesis and Influence on Outcomes
Inflammation & Allergy - Drug Targets (Discontinued) Effect of Treatment with Caspofungin on the Diagnosis of Fungal Infections by Gamma Scintigraphy
Current Radiopharmaceuticals Nanomaterials for Photohyperthermia: A Review
Current Pharmaceutical Design Biofilms: New Ideas for An Old Problem
Recent Patents on Biotechnology Targeting RGD Recognizing Integrins: Drug Development, Biomaterial Research, Tumor Imaging and Targeting
Current Pharmaceutical Design Daptomycin: A Review of Properties, Clinical Use, Drug Delivery and Resistance
Mini-Reviews in Medicinal Chemistry Perceval Sutureless Valve – are Sutureless Valves Here?
Current Cardiology Reviews The Deadly Quartet (Covid-19, Old Age, Lung Disease, and Heart Failure) Explains Why Coronavirus-Related Mortality in Northern Italy Was So High
Current Cardiology Reviews Prevention of Microbial Communities: Novel Approaches Based Natural Products
Current Pharmaceutical Biotechnology Continuous Infusion of Antibiotics in Critically Ill Patients
Current Clinical Pharmacology Combined Brain/Heart Magnetic Resonance Imaging in Systemic Lupus Erythematosus
Current Cardiology Reviews Early Postoperative Bleeding in Polytrauma Patients Treated with Fondaparinux: Literature Review and Institutional Experience
Current Vascular Pharmacology Calcific Aortic Stenosis: Molecular and Cellular Mechanisms, Medical Treatment Alternatives
Current Cardiology Reviews