scholarly journals Facile Synthesis and Antimicrobial Evaluation of Some New Heterocyclic Compounds Incorporating a Biologically Active Sulfamoyl Moiety

2014 ◽  
Vol 2014 ◽  
pp. 1-10
Author(s):  
Elham S. Darwish
Keyword(s):  
Heterocyclic Compounds ◽  
Antimicrobial Agents ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
Phenyl Isothiocyanate ◽  
Convenient Synthesis ◽  
Triazine Derivatives ◽  
Antimicrobial Evaluation ◽  
Arenediazonium Salt

A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reactedin situwith chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, keteneN,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.

Synthesis and Evaluation of 2, 3, 4, 6-Tetra-Substituted-2, 3-Dihydropyridine Derivatives as Novel Antimicrobial Agents

2018 ◽  
Vol 11 (5) ◽  
pp. 4268-4274
Author(s):  
Bhagavaan Raju M ◽  
A. Ramesh A ◽  
A Raghuram Rao
Keyword(s):  
Heterocyclic Compounds ◽  
Antimicrobial Agents ◽  
Aromatic Aldehydes ◽  
Biologically Active ◽  
Diffusion Method ◽  
Antimicrobial Compounds ◽  
Pyridine Derivatives ◽  
Proteus Vulgaris ◽  
Agar Diffusion Method ◽  
Dihydropyridine Derivatives

The present study has been carried out to synthesize and screen certain heterocyclic antimicrobial compounds with clues from the biologically potent activities of heterocyclic compounds containing pyridine. With a view to synthesize some biologically active compounds, it has been felt worthwhile to study the synthesis of 2, 3, 4, 6-tetra-substituted-2,3-dihydro pyridine derivatives (7a-t). They were synthesized by the condensation of respective 2-amino-2,3-dihydropyridines with different aromatic aldehydes. 7a-t were purified and characterized by physical and spectral methods (IR, 1HNMR & MS). All the compounds were evaluated for their antimicrobial activity by the agar diffusion method against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Proteus vulgaris, Candida albicans and Saccharomyces cerevisiae. All the compounds exhibited mild to moderate antibacterial & antifungal activity. Among these compounds, compound 7h (R= Cl, R1=Cl) showing greater inhibitory activity against all tested organisms employed with zones inhibition of 20 to 15 mm at a concentration of 150 μ g/mL. Compounds 7g, 7c, 7i and 7j have been found as the next in the order of its antimicrobial potency. These compounds have the potential as novel antimicrobial agents. 

scholarly journals Synthesis and biological activity of 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide derivatives

ADMET & DMPK ◽  
2021 ◽  
Author(s):  
Svetlana Meshcheryakova ◽  
Alina Shumadalova ◽  
Ozal Beylerli ◽  
Ilgiz Gareev
Keyword(s):  
Antimicrobial Agents ◽  
Biologically Active ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial Screening ◽  
Microbial Inhibition ◽  
Antimicrobial Evaluation ◽  
Temperature Interaction ◽  
Antibacterial And Antifungal ◽  
New Compounds ◽  
Base Object

The synthesis and antimicrobial evaluation of new 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide derivatives was investigated. According to the literature, there are a lot of antimicrobial agents among the pyrimidines and hydrazides, and therefore it seems promising to use 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide as a base object for synthesizing new biologically active substances. 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide was obtained by the hydrazinolysis of ethyl thioacetate, using a 3-fold molar excess of 85 % hydrazine hydrate in ethanol, at room temperature. Interaction of 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]­acetohydrazide with ketones during boiling in ethanol yielded N-ylidenehydrazides. The solid obtained by concentration was collected, and then purified by recrystallization. The new compounds were characterized by 1H, 13C NMR, IR spectroscopy and elemental analysis. The antibacterial and antifungal activities of the new compounds were analysed using agar diffusion and tenfold broth (pH 7.2 – 7.4) dilution methods, in comparison with the clinical used drugs, ceftriaxone and Pimafucin. The structure–activity studies showed that, depending on the nature of the hydrazide fragment, the newly synthesized compounds exhibited varying degrees of microbial inhibition. Within the same series the antimicrobial activity depends on the nature of the substituent attached to the benzene ring. The investigation of antibacterial screening data revealed that the compounds Nʹ-[1-(4-aminophenyl)ethylidene]-2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide, Nʹ-[1-(4-hydroxyphenyl)ethylidene]-2-[6-methyl-4-(thi­­etan­-3-yloxy)pyrimidin-2-ylthio]acetohydrazide, Nʹ-[1- (2,5-dihydroxyphenyl) ethylidene]-2-[6-methyl-4-(thietan-3-yloxy)-pyrimidin-2-ylthio]acetohydrazide were found to be more potent than the other synthesized analogues.

scholarly journals Synthesis, Molecular Docking, MEP and SAR Analysis, ADME-Tox Predictions, and Antimicrobial Evaluation of Novel Mono- and Tetra-Alkylated Pyrazole and Triazole Ligands

2021 ◽  
Vol 2021 ◽  
pp. 1-11
Author(s):  
Y. Kaddouri ◽  
B. Bouchal ◽  
F. Abrigach ◽  
M. El Kodadi ◽  
M. Bellaoui ◽  
...  
Keyword(s):  
Heterocyclic Compounds ◽  
Antimicrobial Agents ◽  
Antibacterial Activities ◽  
Protein Docking ◽  
Bacterial Strains ◽  
Lead Compounds ◽  
Antimicrobial Evaluation ◽  
Pharmaceutical Industries ◽  
Sar Analysis

Newly synthesized compounds of N-alkylated heterocyclic compounds were prepared by condensation of amine with alcohol which undergoes a reaction of SN2. These newly synthesized derivatives were characterized by spectral analysis. The objective is to prepare new potent nontoxic antimicrobial agents which are easy to synthesize and could be scaled up in pharmaceutical industries. Thirteen new heterocyclic compounds containing a pyrazole moiety were synthesized with good yields (29.79 to 99.6%) and were characterized by FTIR, 1H NMR, 13C NMR, and CG-MS techniques. The compounds were divided into two series—monoalkylated compounds (1–11) and tetra-alkylated compounds (12 and 13)—and then evaluated for their in vitro antifungal and antibacterial activities against several fungal and bacterial strains. None of the monoalkylated compounds had antibacterial or antifungal activity. However, the two tetra-alkylated pyrazole ligands displayed strong antibacterial potential. Moreover, compound 12 was more potent against all tested bacterial strains than compound 13. Interestingly, compounds 12 and 13 acted as weak antifungal agents against Saccharomyces cerevisiae. ADME-Tox studies suggested that compounds 12 and 13 exhibit better toxicity profiles than the commercial antibiotic streptomycin. MEP studies suggested that compounds 12 and 13 have the same charge locations but differ in their values which are due to the condensed geometry of compound 13 that make it more polarizable than compound 12. Of particular interest, these different MEPs were evident in ligand protein docking, suggesting that compound 12 has better affinity with MGL enzyme than compound 13. All these findings suggested that these novel compounds represent promising antibacterial lead compounds.

scholarly journals Synthesis, structural characterization and antimicrobial evaluation of some novel piperidin-4-one oxime esters

2015 ◽  
Vol 80 (9) ◽  
pp. 1101-1111 ◽  
Author(s):  
Gokula Krishnan ◽  
R. Sivakumar ◽  
V. Thanikachalam
Keyword(s):  
Biologically Active ◽  
Good Activity ◽  
Mass Spectral ◽  
Antibacterial And Antifungal Activities ◽  
Xrd Study ◽  
Antimicrobial Evaluation ◽  
Ft Ir ◽  
Antibacterial And Antifungal

Fifteen novel biologically active piperidin-4-one oxime esters (8-22) have been synthesized with good yields. These compounds were prepared from in-situ activated carboxylic acids using POCl3 and pyridine with piperidin-4- one oximes. The structure of the title compounds were elucidated on the basis of FT-IR, NMR (1D and 2D) and mass spectral analyses. The single crystal XRD study of compounds 12 and 20 were the further evidence for the proposed structure unambiguously. All the synthesized compounds were tested for in vitro antibacterial and antifungal activities. Many of these derivatives exhibited good activity against Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli, Trigoderma veride and Aspergillus flavus.

scholarly journals 2-Acetylbenzimidazole: a Valuable Synthon for the Synthesis of Biologically Active Molecules

2020 ◽  
Vol 11 (4) ◽  
pp. 11562-11591
Keyword(s):  
Heterocyclic Compounds ◽  
Heterocyclic System ◽  
Biological Activities ◽  
Biologically Active ◽  
Online Search ◽  
Convenient Synthesis ◽  
Anti Cancer ◽  
Pharmacological Interest ◽  
Main Motive ◽  
Biological Aspects

Benzimidazole is an important moiety from a medicinal chemistry perspective due to its various biological activities such as antimicrobial, anti-cancer, anti-diabetic, anti-Alzheimers, and anti-inflammatory, etc. 2-acetylbenzimidazole is exploited to obtain various heterocyclic compounds of pharmacological interest. This review's main motive is to present the literature on 2-acetylbenzimidazole chemistry and provide valuable and up-to-date information for its applications. The present review is carried out by compiling literature from 1964 to 2020 concerning the synthesis and biological aspects of various heterocyclic compounds derived from 2-acetylbenzimidazole. Literature was collected from various online search engines viz. Google Scholar, PubMed, Science Direct, Core, and Semantic scholar. 2-acetylbenzimidazole has been successfully employed as a synthon to obtain heterocyclic system viz. oxirane, pyrazoline, thiazole, pyrazole, isoxazoline, isoxazole, pyridine, pyrimidine, thiazine, diazepine, and other miscellaneous rings. 2-acetylbenzimidazole has shown promise for the convenient synthesis of various heterocyclic compounds. The reactions can be carried out on various reactive sites of 2-acetylbenzimidazole, which are the carbonyl group and the amino group. This review will help to explore various heterocyclic compounds and particularly in the synthesis of biologically useful compounds.

A REVIEW ON RECENT ADVANCES IN CHEMISTRY, SYNTHESIS AND BIOLOGICAL APPLICATIONS OF ISATIN DERIVATIVES

2018 ◽  
pp. 16-22
Author(s):  
Shukla PK ◽  
Singh MP ◽  
Patel R
Keyword(s):  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Biological Applications ◽  
Plant Origin ◽  
Recent Past ◽  
Pharmacological Activities ◽  
Naturally Occurring ◽  
Recent Advances ◽  
Biological Aspects ◽  
Isatin Derivatives

Indole and its derivatives have engaged a unique place in the chemistry of nitrogen heterocyclic compounds. The recognition of the plant growthhormone, heteroauxin, the significant amino acids, tryptamine & tryptophan and anti-inflammatory drug, indomethacine are the imperativederivatives of indole which have added stimulus to this review work. Isatin (1H-indole-2,3-dione), an indole derivative of plant origin. Althoughit is a naturally occurring compound, but was synthesized by Erdmann and Laurent in 1840 before it was found in nature. Isatin is a versatileprecursor for many biologically active molecules and its diversified nature makes it a versatile substrate for further modifications. It is concernedin many pharmacological activities like anti-malarial, antiviral, anti-allergic, antimicrobial etc; isatin and its derivatives have been also found todemonstrate promising outcomes against various cancer cell lines. This review provides a brief overview on the recent advances and futureperspectives on chemistry and biological aspects of isatin and its derivatives reported in the recent past.

Antistaphylococcal activity of carbonic acid extract of hops

2018 ◽  
Vol 22 (2) ◽  
pp. 297-300
Author(s):  
V.V. Nevmerzhitsky ◽  
V.Yu. Ivannik ◽  
V.V. Kazmirchuk ◽  
T.N. Moiseenko ◽  
T.A. Volkov ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Antimicrobial Agents ◽  
Carbonic Acid ◽  
Inflammatory Diseases ◽  
Acquired Resistance ◽  
Biologically Active ◽  
Antibacterial Drugs ◽  
Antistaphylococcal Activity ◽  
Prevention And Treatment ◽  
Main Disadvantage

The fight against staphylococcal infection, increasing the effectiveness of methods of prevention and treatment of diseases of staphylococcal etiology is of interest to scientists and practitioners, both in Ukraine and around the world. The urgency of this problem is growing rapidly, as there is a tendency to increase the resistance of not only staphylococci, but also other gram-positive bacteria. The spread of methicillin-resistant staphylococci restricts the choice of antibiotics for the treatment of diseases of staphylococcal etiology. Staphylococcus aureus is the most common and dangerous type, which is one of the main factors of purulent-inflammatory lesions of the skin and mucous membranes. As a result of mutations, pathogenic staphylococci acquired resistance to antibacterial drugs. The main disadvantage of modern antibiotics is their non-selectivity. As a result of mutations, pathogenic staphylococci acquired resistance to antibacterial drugs. The main disadvantage of modern antibiotics is their non-selectivity. One of the unique and promising medicinal plants, which contains a rich complex of biologically active substances (BAS), is common hops (Humulus lupulus L.). The complex of BAS (flavonoids, hormones, vitamins, bitter, phenolic compounds, essential oils) causes anti-inflammatory, bactericidal, hyposensitizing and analgesic action of hops. The purpose of this work is to determine the antistaphylococcal activity of the carbon dioxide extract of hops and to justify the development on its basis of new antimicrobial agents for the prevention and treatment of infectious and purulent-inflammatory diseases. The following methods were used: microbiological (method of diffusion into agar (well method)) and mathematical and statistical. The high antimicrobial activity of the carbon dioxide extract of hops has been established for museum test strains of the genus Staphylococcus. The results of the studies testify to the prospects of further study of the bactericidal properties of the extract of hops carbon dioxide with the aim of creating effective antimicrobial agents on its basis for the prevention and treatment of infectious and purulent-inflammatory diseases of staphylococcal etiology.

Biologically Active 2,5-Disubstituted-1,3,4-Oxadiazoles

2009 ◽  
Vol 2 (1) ◽  
pp. 390-406
Author(s):  
Harish Rajak ◽  
Murli Dhar Kharya ◽  
Pradeep Mishra
Keyword(s):  
Heterocyclic Compounds ◽  
Medical Literature ◽  
Biological Activities ◽  
Biologically Active ◽  
Pharmacological Properties ◽  
Clinical Use ◽  
Synthetic Drugs ◽  
Physiologic Activity ◽  
Pharmacologically Active

There are vast numbers of pharmacologically active heterocyclic compounds in regular clinical use. The presence of heterocyclic structures in diverse types of compounds is strongly indicative of the profound effects such structure exerts on physiologic activity, and recognition of this is abundantly reflected in efforts to find useful synthetic drugs. The 1,3,4-oxadiazole nucleus has emerged as one of the potential pharmacophore responsible for diverse pharmacological properties. Medical Literature is flooded with reports of a variety of biological activities of 2,5-Disubstituted-1,3,4-oxadiazoles. The present work is an attempt to summarize and enlist the various reports published on biologically active 2,5-disubstituted-1,3,4-oxadiazoles.

Oxazole-Based Compounds As Anticancer Agents

2020 ◽  
Vol 26 (41) ◽  
pp. 7337-7371 ◽  
Author(s):  
Maria A. Chiacchio ◽  
Giuseppe Lanza ◽  
Ugo Chiacchio ◽  
Salvatore V. Giofrè ◽  
Roberto Romeo ◽  
...  
Keyword(s):  
Cancer Research ◽  
Drug Discovery ◽  
Anticancer Agents ◽  
Heterocyclic Compounds ◽  
Chemical Diversity ◽  
Biologically Active ◽  
New Drugs ◽  
The Core ◽  
Anti Cancer ◽  
Biologically Active Derivatives

: Heterocyclic compounds represent a significant target for anti-cancer research and drug discovery, due to their structural and chemical diversity. Oxazoles, with oxygen and nitrogen atoms present in the core structure, enable various types of interactions with different enzymes and receptors, favoring the discovery of new drugs. Aim of this review is to describe the most recent reports on the use of oxazole-based compounds in anticancer research, with reference to the newly discovered iso/oxazole-based drugs, to their synthesis and to the evaluation of the most biologically active derivatives. The corresponding dehydrogenated derivatives, i.e. iso/oxazolines and iso/oxazolidines, are also reported.

Heterocycle Compounds with Antimicrobial Activity

2020 ◽  
Vol 26 (8) ◽  
pp. 867-904 ◽  
Author(s):  
Maria Fesatidou ◽  
Anthi Petrou ◽  
Geronikaki Athina
Keyword(s):  
Heterocyclic Compounds ◽  
Bacterial Infections ◽  
Scientific Community ◽  
Antimicrobial Agents ◽  
Fungal Infections ◽  
Biological Activities ◽  
Literature Survey ◽  
New Findings ◽  
Wide Range ◽  
Number Of Microorganisms

Background: Bacterial infections are a growing problem worldwide causing morbidity and mortality mainly in developing countries. Moreover, the increased number of microorganisms, developing multiple resistances to known drugs, due to abuse of antibiotics, is another serious problem. This problem becomes more serious for immunocompromised patients and those who are often disposed to opportunistic fungal infections. Objective: The objective of this manuscript is to give an overview of new findings in the field of antimicrobial agents among five-membered heterocyclic compounds. These heterocyclic compounds especially five-membered attracted the interest of the scientific community not only for their occurrence in nature but also due to their wide range of biological activities. Method: To reach our goal, a literature survey that covers the last decade was performed. Results: As a result, recent data on the biological activity of thiazole, thiazolidinone, benzothiazole and thiadiazole derivatives are mentioned. Conclusion: It should be mentioned that despite the progress in the development of new antimicrobial agents, there is still room for new findings. Thus, research still continues.

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