Synthesis and antibacterial activity of thieno[3,2-c]pyridine benzohydrazides.
Journal name: World Journal of Pharmaceutical Research
Original article title: Synthesis and antibacterial activity of benzohydrazide derivatives linking thieno[3,2- c]pyridine nucleus
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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N. Sree Lakshmana Rao, Mandava V. Basaveswara Rao and KRS Prasad
World Journal of Pharmaceutical Research:
(An ISO 9001:2015 Certified International Journal)
Full text available for: Synthesis and antibacterial activity of benzohydrazide derivatives linking thieno[3,2- c]pyridine nucleus
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
Doi: 10.20959/wjpr201714-10005
Copyright (license): WJPR: All rights reserved
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Summary of article contents:
Introduction
The study presented in the World Journal of Pharmaceutical Research focuses on the synthesis and antibacterial activity of thieno[3,2-c]pyridine-hydrazide-hydrazone derivatives. With the increasing challenge posed by multidrug-resistant bacterial pathogens, there is an urgent demand for new antibacterial agents. The researchers explored the potential of hydrazone compounds, which have shown a range of pharmacological activities, including antimicrobial properties. The targeted compounds were synthesized from thiophene aldehyde, characterized through various analytical techniques, and evaluated for their effectiveness against multiple bacterial strains.
Synthesis of Thieno[3,2-c]pyridine Hydrazide-Hydrazone Derivatives
The research details a multi-step synthetic approach to create thieno[3,2-c]pyridine-hydrazide-hydrazone derivatives (9a-9j). The procedure begins with synthesizing a key intermediate, N-(2-formylthieno[3,2-c]pyridin-4-yl) benzamide (compound 7), from commercially available 2-thiophenaldehyde. This was followed by reactions involving various benzohydrazides to form the desired hydrazone derivatives, leading to compounds with promising antibacterial properties. The synthetic process was characterized by its efficiency and high yielding steps, showcasing the potential for developing new antibacterial agents.
Antibacterial Activity Evaluation
The synthesized compounds were subjected to antibacterial testing against both Gram-positive and Gram-negative bacteria, including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pyogenes. The testing used the agar diffusion method with Norfloxacin serving as a reference. Results indicated that certain derivatives, particularly 9i (R = 4-SO₂Me) and 9f (R = 4-OH), exhibited excellent antibacterial activity, while others showed varying degrees of efficacy. Notably, some compounds (9a, 9b, 9c, and 9g) displayed negligible activity against the bacterial strains tested, highlighting the variability in effectiveness among the derivatives.
Structural Characterization and Analysis
The synthesized compounds were effectively characterized using several analytical techniques, including IR, mass spectrometry, and NMR spectroscopy. The detailed spectral analysis provided insight into the structure-activity relationships of the compounds. The molecular characterization confirmed that the compounds retained the expected functional groups and structural features conducive to antibacterial activity. For instance, specific shifts and patterns observed in the NMR spectra were indicative of the chemical environments around the functional groups. This correlation between structure and activity underscored the further exploration of these compounds for potential therapeutic applications.
Conclusion
The study successfully synthesized a series of thieno[3,2-c]pyridine-hydrazide-hydrazone derivatives and evaluated their antibacterial properties. The promising results of compounds like 9i and 9f suggest a pathway for developing new antibacterial agents to combat multidrug-resistant bacteria. The research adds to the existing knowledge of hydrazone compounds' pharmacological potential and emphasizes the need for continuous exploration of novel antibacterial agents with unique mechanisms of action. Further investigations into the structure-activity relationships will be essential for optimizing these compounds for clinical use.
FAQ section (important questions/answers):
What does the paper aim to achieve with hydrazide-hydrazone derivatives?
The paper focuses on synthesizing and evaluating antibacterial activity of thieno[3,2-c]pyridine hydrazide-hydrazone derivatives, addressing the need for new antibacterial agents due to multidrug-resistant pathogens.
What methods were used to synthesize the derivatives?
The synthesis involved several chemical reactions, including Knoevenagel condensation, Curtius rearrangement, and selective chlorination, employing reagents like TBAB, cyanuric chloride, and triphenylphosphine under varying conditions.
Which bacterial strains were tested against the synthesized compounds?
The antibacterial activity was tested against Gram-positive strains Staphylococcus aureus and Streptococcus pyogenes, as well as Gram-negative strains Escherichia coli and Pseudomonas aeruginosa.
What were the significant findings regarding antibacterial activity?
Compounds 9i (R = 4-SO2Me) and 9f (R = 4-OH) showed excellent antibacterial activity, while several other derivatives exhibited good activity compared to the reference drug Norfloxacin.
How were the newly synthesized compounds characterized?
The synthesized hydrazone derivatives were characterized using 1H NMR, mass spectrometry, and infrared spectroscopy, confirming their structures and purity.
What is the significance of hydrazone compounds in drug development?
Hydrazone compounds are important in drug development due to their diverse pharmacological activities, which include antifungal, anticancer, and anticonvulsant effects, aiding the search for effective treatment options against resistant infections.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “Synthesis and antibacterial activity of thieno[3,2-c]pyridine benzohydrazides.”. 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:
The term 'Activity' refers to the biological effect that a compound has when tested, particularly regarding how effectively it can inhibit or kill bacteria in the context of antibacterial research. Evaluating the activity of synthesized compounds informs researchers about their potential therapeutic uses and effectiveness in combating infections.
2) Antibiotic (Antibacterial):
An antibiotic is a broader term for substances that kill or inhibit the growth of bacteria, a primary focus in this research. The distinction between 'antibiotic' and 'antibacterial' is notable, as antibiotics typically refer to a subset of antibacterial compounds with medical applications.
3) Drug:
A drug is a chemical substance used for medical treatment, particularly for preventing, diagnosing, or curing diseases. In the context of this paper, the focus is on the development of new drugs derived from hydrazone derivatives, aiming to improve antibacterial efficacy and address resistance.
4) Water:
Water serves as a solvent in many chemical reactions and is highlighted in the synthesis protocols described in the paper. Its role in facilitating reactions under microwave irradiation emphasizes the importance of environmental sustainability and the use of green chemistry principles in drug development.
5) Machilipatnam:
Machilipatnam is a coastal town in Andhra Pradesh, India, where the research occurred. The geographic location is relevant as the researchers are affiliated with Krishna University located in the town, indicating the regional significance of the study in contributing to local pharmaceutical research and educational initiatives.
6) Krishna (Krsna):
Krishna refers to Krishna University, which is based in Machilipatnam, Andhra Pradesh, India. The university is significant for nurturing academic research in chemistry and pharmacology, directly supporting the investigation into new antibacterial agents, which represents an essential part of the academic landscape in the region.
7) India:
India is the country where the research took place, and it illustrates the growing importance of scientific research in developing new medications in response to public health challenges. The country's rich biodiversity and pharmaceutical sector provide a unique foundation for innovative drug discovery involving traditional and modern compounds.
8) Mandava (Mamdava):
Mandava V. Basaveswara Rao is a key author and researcher involved in the study. His contributions are critical in advancing the synthesis and evaluation of new antibacterial agents, demonstrating the importance of collaboration among scholars in academia to tackle pressing health issues.
9) Aureus:
Staphylococcus aureus is a type of bacteria that can cause various infections in humans and is one of the targeted pathogens in the antibacterial activity assays described in the study. Its significance highlights the ongoing challenge in treating infections caused by resistant strains, underpinning the research's relevance.
10) Lakshmana (Laksmana):
N. Sree Lakshmana Rao, a primary author of the research, indicates the collaborative effort in scientific discovery within academia. His involvement emphasizes the importance of educational institutions and researchers in developing new therapeutic agents, which is crucial in addressing contemporary health crises.
11) Heating:
Heating refers to the application of thermal energy in chemical reactions, a crucial step in the synthesis processes detailed in the study. It is important in facilitating the transformation of compounds, thereby enhancing yield and ensuring the efficacy of the synthesized antibacterial agents.
12) Table:
The term 'Table' is related to the presentation of data within the paper, particularly summarizing the antibacterial activity results of the synthesized compounds. Such organized presentations enable readers to quickly grasp outcomes, trends, and comparative effectiveness of different compounds tested against bacterial strains.
13) Study (Studying):
Study signifies the overall research endeavor undertaken to explore the synthesis and evaluation of new antibacterial compounds. It encompasses various methodologies, screenings, and interpretations of results, providing valuable insights into drug development and addressing antibacterial resistance.
14) New Delhi:
New Delhi is the capital of India, representing a hub for research and policy-making in the country. Its mention could reflect collaboration or funding opportunities with various institutions, underlining the vital role urban centers play in advancing scientific research and public health initiatives.
15) Transformation (Transform, Transforming):
Transformation refers to the chemical changes that compounds undergo during synthesis, a key theme in the study of creating new hydrazone derivatives. Understanding these transformations is crucial for optimizing reaction conditions and maximizing yields in drug discovery.
16) Discussion:
Discussion serves as a section in the paper where findings are interpreted and contextualized concerning existing literature and future directions. It reflects on the significance of the results, exploring implications for further research and potential pathways for developing new antibacterial therapies.
17) Tirumala (Thirumala):
Thirumala Chary is likely a contributing author or collaborator in the research effort, indicative of interdisciplinary collaboration in the synthesis and study of new antibacterial agents. The inclusion of multiple researchers highlights the importance of teamwork in achieving comprehensive scientific outcomes.
18) Substance:
Substance refers to the chemical compounds synthesized and evaluated in the study, such as hydrazone derivatives. The exploration of various substances is foundational to the research, as it aims to identify new candidates for effective antibacterial therapy.
19) Venkata (Vemkata):
Venkata is part of Venkata Satyanarayana, another author involved in the research. This underscores the collaborative nature of scientific inquiry, where combined expertise contributes to developing new compounds and evaluating their potential as antibacterial agents.
20) Disease:
Disease encompasses the various infections caused by bacteria, which the study aims to address through the development of new antibacterial compounds. Understanding the pathogenesis of diseases is crucial to tailoring effective treatment options that can combat resistant strains effectively.
21) Shukla (Sukla):
Shukla is a name mentioned in the context of contributors or references, possibly denoting additional expertise or validation in the field of pharmaceutical research. Such contributions provide a broader context and reinforce the collaborative nature of scientific discovery.
22) Harada:
Harada is likely a referenced author or contributor to related work in the field, indicating the international collaboration and communication in scientific research necessary for advancement in drug development and understanding antibacterial medication.
23) Medium:
Medium refers to the chemical environment in which reactions occur, such as solvents used in synthesis. The choice of medium significantly influences reaction outcomes and product purity, underscoring the importance of selecting appropriate conditions to achieve desired results.
24) Delhi:
Delhi, particularly New Delhi, denotes an important administrative and academic center in India known for its contribution to education and research. Scholars and institutions in this area are pivotal in advancing initiatives aimed at combating public health challenges, such as infectious diseases.
25) Patel:
Patel likely refers to an author or researcher contributing to the study, illustrating the collaborative nature of drug development. The interactions among various researchers represent an essential framework for generating innovative solutions to combat bacterial resistance.
26) Chary:
Chary, associated with the work of Thirumala Chary, indicates another contributor to the research. This reference highlights the collaborative effort in addressing complex challenges in drug synthesis and the importance of diverse expertise in successful research initiatives.
27) Tata:
Tata relates to Tata McGraw Hill, a prominent publishing house known for its educational resources. The mention suggests a connection to extensive academic and professional literature platforms that provide reference materials crucial for conducting rigorous scientific research.
28) Chan:
Chan, likely a researcher or a reference to works in the field, points to the role of contributions from various authors that enrich the discourse in antibacterial research. Collaborative efforts and shared data are fundamental to advancing discoveries in pharmaceuticals.
Other Science Concepts:
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Antibacterial activity, Anti-inflammatory activity, Antidepressant activity, Anticancer activity, Drug development, Anticonvulsant activity, Thin Layer Chromatography (TLC), Gram-positive and Gram-negative bacteria, Zones of inhibition, Antimalarial activity, Pharmacologically active substance, Experimental procedure, Agar diffusion method, Antimycobacterial activity, Synthesis and Characterization, Fluorescence properties.