Synthesis of bioactive 2-azetidinones and their pharmacological activity.
Journal name: World Journal of Pharmaceutical Research
Original article title: A facile synthesis of bio active 2-azetidinones derivatives and their pharmacological activity
The WJPR includes peer-reviewed publications such as scientific research papers, reports, review articles, company news, thesis reports and case studies in areas of Biology, Pharmaceutical industries and Chemical technology while incorporating ancient fields of knowledge such combining Ayurveda with scientific data.
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Summary of article contents:
Introduction
Azetidine-2-ones, specifically β-lactam heterocycles, represent a significant class of compounds with notable biological activities and are widely recognized for their use in various antibiotic medications, including penicillins and cephalosporins. These heterocycles are crucial due to their antibiotic properties; however, the emergence of antibiotic-resistant bacteria necessitates the continual search for new compounds that can combat infections effectively. The paper presents a facile synthesis of 2-azetidinone derivatives and investigates their pharmacological activities, particularly focusing on their antimicrobial effects against both Gram-positive and Gram-negative bacteria.
Synthesis of Azetidinones
The synthesis of the azetidine-2-ones, specifically the 3-chloro-2-oxo derivatives (designated 7a-h), follows a method that involves the conversion of Schiff bases (6a-h) into the desired azetidinone structure. The initial step includes refluxing the Schiff bases with chloroacetyl chloride in the presence of triethylamine (TEA) in a dioxane solvent, resulting in a 60-65% yield of the azetidinone compounds. The structural characterization of these compounds was subsequently confirmed via various techniques, including IR, NMR, and mass spectral analysis, highlighting the effective methodology employed in their synthesis.
Antimicrobial Activity Assessments
The antimicrobial efficacy of the synthesized compounds was assessed using a disc diffusion technique against several bacterial strains: Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. The experimental results revealed that almost all synthesized compounds exhibited promising antibacterial activity, though their effectiveness was comparatively lower than standard antibiotics like ampicillin and chloramphenicol. Particularly, compounds 7c, 7d, 7f, and 7g demonstrated significant antibacterial properties, establishing a clear relevance of these azetidinone derivatives in therapeutic applications.
Spectral Analysis and Characterization
Spectral analysis confirmed the structural integrity and composition of the synthesized compounds. Infrared spectroscopy revealed characteristic functional group vibrations, confirming the presence of β-lactam and sulfonamide functionalities. NMR spectra further elucidated the arrangements of hydrogen and carbon atoms within the azetidinone structure. The study emphasizes the relationship between molecular structure and biological activity, providing insight into how modifications to the azetidinone core can influence antimicrobial effectiveness.
Conclusion
The study successfully synthesizes a new series of azetidinone derivatives and emphasizes their potential as antibacterial agents. Despite some compounds showing moderate to excellent antimicrobial activity, the research underlines the challenge of competing with established antibiotics. These findings pave the way for future investigations aimed at improving the efficacy of azetidinone derivatives, which may prove beneficial in the ongoing fight against antibiotic-resistant bacterial strains. Overall, the exploration of these compounds offers valuable contributions to medicinal chemistry and antimicrobial research.
Original source:
This page is merely a summary which is automatically generated hence you should visit the source to read the original article which includes the author, publication date, notes and references.
Kokila A. Parmar, Chetan J. Vasava and Sarju N. Parajapati
World Journal of Pharmaceutical Research:
(An ISO 9001:2015 Certified International Journal)
Full text available for: A facile synthesis of bio active 2-azetidinones derivatives and their pharmacological activity
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
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FAQ section (important questions/answers):
What are azetidine-2-ones and their significance in pharmacology?
Azetidine-2-ones are a class of heterocycles known for their biological importance, particularly in antibiotics. They exhibit various therapeutic activities, including antibacterial, antifungal, and anticonvulsant effects.
How were the azetidine-2-ones synthesized in this study?
The synthesis involved converting imines (Schiff bases) to azetidine-2-ones via monochloro acetyl chloride. The compounds were characterized using IR, NMR, and mass spectral studies.
What microorganisms were tested for antimicrobial activity in this study?
The antimicrobial activity was tested against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa using the disc diffusion technique.
Did the synthesized compounds exhibit strong antimicrobial activity?
All synthesized compounds showed promising antimicrobial activity; however, their effectiveness was less than that of the standard drugs tested.
What methods were used for spectral characterization of the compounds?
The synthesized compounds were characterized using infrared (IR), proton NMR (1H-NMR), carbon NMR (13C-NMR), and mass spectrometry for comprehensive structural confirmation.
What are the potential therapeutic applications of 2-azetidinone derivatives?
2-Azetidinone derivatives can serve as potent therapeutic agents with activities such as antimicrobial, anti-inflammatory, anticonvulsant, and antitumor effects, making them valuable in pharmaceutical research.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “Synthesis of bioactive 2-azetidinones and their pharmacological activity.”. This list explains important keywords that occur in this article and links it to the glossary for a better understanding of that concept in the context of Ayurveda and other topics.
1) Activity:
Activity in this context refers to the biological effectiveness of the synthesized compounds against various microorganisms. Specifically, it relates to their ability to inhibit the growth of bacterial strains like Bacillus subtilis and Staphylococcus aureus. The study measures this activity in terms of the zone of inhibition, providing insights into potential therapeutic uses.
2) Water:
Water is a crucial reagent in various chemical processes, serving as a solvent in synthesizing compounds. In this study, it is used in reactions involving the reflux of mixture constituents, indicating its importance in dissolving reactants and facilitating reactions during the preparation and workup of the synthesized azetidinones.
3) Table:
A table is employed in scientific research to effectively summarize and present data, such as physical characteristics, antimicrobial activity, or spectral data of synthesized compounds. It allows readers to quickly grasp key information, aiding in comparisons and understanding the outcomes of experiments, particularly in biological and chemical studies.
4) Aureus:
Aureus, specifically Staphylococcus aureus, is a significant pathogenic bacterium that this study investigates for its susceptibility to synthesized antibiotics. The presence of this microorganism as a test subject reflects the focus on developing effective antibacterial agents capable of combating common infections, thereby indicating the relevance of the compounds studied.
5) Antibiotic (Antibacterial):
Antibacterial relates to the ability of a substance to inhibit or kill bacteria. The study's focus on synthesizing azetidinone derivatives with potential antibacterial properties signifies the intention to discover new treatments capable of addressing bacterial infections, particularly in a medical landscape marked by increasing antibiotic resistance challenges.
6) India:
India represents the country where the research was conducted, highlighting its significance in the global scientific community. The synthesis and evaluation of bioactive compounds contribute to India's role in pharmaceutical developments. This regional context provides insight into the local scientific environment and the research capabilities situated in Indian educational institutions.
7) Study (Studying):
Study indicates a systematic investigation aimed at exploring the synthesis, characterization, and biological properties of new azetidinone derivatives. It involves assessing antimicrobial activity and validating structural composition through various analytical techniques, representing a methodical approach to advancing medicinal chemistry and discovering new therapeutic agents.
8) Drug:
Drug represents the end goal of pharmaceutical research, where synthesized compounds are evaluated for their therapeutic potentials. In this context, the compounds are screened for their antimicrobial activity, aiming to develop new drugs that provide effective treatment options against bacterial infections, ultimately functioning as life-improving medicinal agents.
9) Purification:
Purification refers to the process of isolating and refining synthesized compounds to obtain a pure product. In this research, techniques such as recrystallization and column chromatography are employed to ensure the compounds' purity, which directly affects their efficacy and safety when assessing their pharmacological activities.
10) Gujarat:
Gujarat is a state in India where part of the research was conducted, providing geographical context to the study. This location emphasizes local contributions to scientific advancements and may reflect regional research initiatives that enhance the pharmaceutical and chemical knowledge base within Indian academia and industry.
11) Lucknow:
Lucknow is notable as the location of the Central Drug Research Institute (CDRI), where analytical and elemental data were provided during the study. The city's role in contributing to pharmaceutical research and development highlights the collaborative nature of scientific inquiry in advancing drug discovery and development efforts.
12) Science (Scientific):
Science represents the systematic pursuit of knowledge through observation, experimentation, and analysis. In the context of this research, it underscores the methodological approaches taken to explore the synthesis and testing of azetidinone compounds, reflecting the importance of scientific rigor in advancing medical and pharmaceutical insights.
13) Kokila (Kokilā):
Kokila refers to Dr. Kokila A. Parmar, the lead researcher of this study. Her involvement exemplifies the contributions of individual scientists to advancing pharmaceutical research. She plays a pivotal role in orchestrating the synthesis, characterization, and biological evaluation of new compounds, embodying the essence of research leadership.
14) Patan (Paṭaṉ, Pāṭaṉ, Pāṭāṇ):
Patan is the city where H.N.G. University is located, emphasizing the academic setting of this research. The association of the university with molecular chemistry research reflects the local institution's commitment to higher education and its contributions to scientific knowledge and development within the field of pharmaceuticals.
15) Pharmacological:
Pharmacological encompasses the study of drug action and interactions within biological systems. This term is relevant to the research as it examines the effects of synthesized azetidinone derivatives on bacterial pathogens, thereby assessing their therapeutic potential and understanding their mechanisms of action at the molecular level.
16) Discussion:
Discussion signifies the methodical analysis that follows findings in scientific research. In this context, it involves interpreting the results of compound synthesis and biological testing, placing them in the broader context of existing knowledge, addressing implications for future research, and fostering understanding of the environmental factors impacting microbial resistance.
17) Vasava (Vāsava, Vashava, Vāsavā):
Vasava refers to the co-author of the research, Chetan J. Vasava. His contribution reflects the collaborative nature of scientific research, where multiple individuals bring their expertise together to achieve common goals, enriching the research process through shared knowledge, diverse skills, and innovative approaches.