Synthesis, characterization, and antimicrobial evaluation of novel spiropiperidones

2015 ◽  
Vol 21 (4) ◽  
pp. 239-243
Author(s):  
Anil K. Tiwari ◽  
Abha Bishnoi ◽  
Anil Kumar Verma ◽  
Shaheen Fatma ◽  
Krishna Srivastava ◽  
...  
Keyword(s):  
Antimicrobial Agents ◽  
Fungal Strains ◽  
Spiro Derivatives ◽  
Antimicrobial Evaluation ◽  
Further Development ◽  
Derivatives Of

AbstractNovel spiro derivatives of piperidone 4a–f were synthesized, characterized, and screened against a panel of different bacterial and fungal strains. The study revealed the potential of these molecules for further development as antimicrobial agents.

scholarly journals Investigation of the activity of new derivatives of 1,3-diazinone-4 and their acyclic precursors with respect to bacteria of the genus Proteus

2018 ◽  
Vol 4 (1) ◽  
pp. 11-17
Author(s):  
Svetlana Luzhnova ◽  
Andrey Voronkov ◽  
Narmina Gabitova ◽  
Souda Billel
Keyword(s):  
Antimicrobial Agents ◽  
Dilution Method ◽  
Species Identity ◽  
Safety Requirements ◽  
Highly Active ◽  
Serial Dilution Method ◽  
The Moment ◽  
New Compounds ◽  
Further Development ◽  
Derivatives Of

Introduction: The present paper provides a study of the activity of the new 1,3-diazinon-4 derivatives and their acyclic precursors under the laboratory cipher PYaTd1, PYaTs2, PYaTs3 and PYaTs4 against microorganisms of the genus Proteus, which is of high importance at the moment as the growing resistance of the Proteus to previously highly active antibiotics dictates the need to search for effective antimicrobial agents that meet modern safety requirements. Materials and Methods: The study of the activity of the compounds was carried out on collection and freshly isolated strains from patients with different pathologies. The strains were identified using the BIOMIC V3 apparatus (Giles Scientific, USA) to verify genus and species identity. The strains used in the study were previously examined for susceptibility to antibacterial drugs by the Disc Method to assess the presence or absence of resistance. The activity of the new compounds was studied by the serial dilution method. Results: The results of the study showed that the compounds PYaTd1, PYaTs2, PYaTs3 and PYaTs4 show a different activity against bacteria of the genus Proteus. The substance PYaTs2 is ineffective. With respect to strains P.mirabilis and P.rettgeri, the minimum inhibitory concentration of the compounds PYaTs3, PYaTs4 and PYaTd1 ranges from 4 μg/ml to 16 μg/ml. Conclusion: Thus, by the average aggregate indices, regardless of the species and strain of bacteria, the most effective compound is PYaTd1, the MIC50 of which is within 10 μg/ml, which proves it to be promising and makes further development worthwhile.

scholarly journals Synthesis and Bioevaluation of 5-Chloro-4-(1,3-Oxazol-5-yl)-1Н-Pyrrole-3-Carboxyamides as Antimicrobial Agents

2020 ◽  
Vol 11 (3) ◽  
pp. 10595-10606
Keyword(s):  
Antimicrobial Agents ◽  
Ester Group ◽  
Alkyl Aryl ◽  
Design And Synthesis ◽  
Consecutive Reactions ◽  
Efficient Construction ◽  
Further Development ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
High Antifungal Activity

This investigation deals with the design and synthesis of new derivatives of pyrrole consisting of modifying atoms of chlorine, amide, and 1,3-oxazole fragments. These compounds can be interesting in the context of research of new antimicrobial agents. Ethyl 5-chloro-4-formyl-1H-pyrrole-3-carboxylates were used as a key substrate for further transformation into target compounds. This process was realized as a direct transformation of an aldehyde fragment into a 1,3-oxazole cycle by van Leusen’s reaction followed by hydrolysis of an ester group, which finally converted a reactant into the corresponding pyrrole-3-carboxylic acid. This acid has been found to be an efficient construction block for the further development of antimicrobial agents. The preparative potential of these compounds has been verified by way of their transformation into a series of carbamides through consecutive reactions with thionyl chloride and alkyl-, aryl, and heterylamines under mild reaction conditions. According to bio screening results, the following two compounds have been chosen as those exhibiting a high anti-staphylococcus activity: 1-butyl-5-chloro-2-methyl-4-(1,3-oxazol-5-yl)-N-[(1,3-thiazol-2-yl]-1H-pyrrole-3-carboxamide and 1-butyl-5-chloro-N-[(3-dimethylaminosulfonyl)phenyl]-2-methyl-4-(1,3-oxazol-5-yl)-1H-pyrrole-3-carboxamide (МІС=7.8 µg/ml), while another one – 5-сhloro-N-(4-chlorophenyl)-4-(1,3-oxazol-5-yl)-2-phenyl-1-propyl-1H-pyrrole-3-carboxamide was selected as a compound exhibiting high antifungal activity (МІС=7.8 µg/ml) against the reference strains Candida albiсans АТСС 885/653 and Aspergillus niger K9.

A New Reactive Ketenaminal: Synthesis, Coupling Reaction, Tautomeric Study, Docking and Antimicrobial Evaluation of the Products

2020 ◽  
Vol 16 (6) ◽  
pp. 761-773
Author(s):  
Huda K. Mahmoud ◽  
Hanadi A. Katouah ◽  
Marwa F. Harras ◽  
Thoraya A. Farghaly
Keyword(s):  
Binding Site ◽  
Antimicrobial Agents ◽  
Coupling Reaction ◽  
Docking Study ◽  
Binding Mode ◽  
Binding Energies ◽  
Simple Method ◽  
Antimicrobial Evaluation ◽  
New Compounds ◽  
Active Methylene

Background: One of the most successful reagents used in the synthesis of the reactive enaminone is DMF-DMA, but it is very expensive with harmful effects on the human health and reacts with special compounds to generate the enaminone such as active methylene centers. Aim: In this article, we synthesized a new ketenaminal by simple method with inexpensive reagents (through desulfurization in diphenylether). Methods: Thus, a novel reactive ketenaminal (enaminone) was synthesized from the desulfurization of 2-((2-(4-chlorophenyl)-2-oxoethyl)thio)-5,7-bis(4-methoxyphenyl)pyrido[2,3-d]pyrimidin- 4(3H)-one with diphenylether. The starting keteneaminal was coupled with diazotized anilines via the known coupling conditions to give a new series of 2-(4-chlorophenyl)-1-(2-(arylhydrazono)-2- oxoethyl)-5,7-bis(4-methoxy-phenyl)pyrido[2,3-d]pyrimidin-4(1H)-ones. Results: The structures of the new compounds were elucidated based on their IR, 1H-NMR, 13CNMR, and Mass spectra. Moreover, the potency of these compounds as antimicrobial agents has been evaluated. The results showed that some of the products have high activity nearly equal to that of the used standard antibiotic. Additionally, the docking study was done to get the binding mode of the synthesized compounds with the binding site of the DHFR enzyme. The results of molecular docking of the synthesized arylhydrazono compounds are able to fit in DHFR binding site with binding energies ranging from -4.989 to -8.178 Kcal/mol. Conclusion: Our goal was achieved in this context by the synthesis of new ketenaminal from inexpensive reagents, which was utilized in the preparation of bioactive arylhydrazone derivatives.

scholarly journals Biguanide-Based Synthesis of 1,3,5-Triazine Derivatives with Anticancer Activity and 1,3,5-Triazine Incorporated Calcium Citrate Nanoparticles

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1028
Author(s):  
Monnaya Chalermnon ◽  
Sarocha Cherdchom ◽  
Amornpun Sereemaspun ◽  
Rojrit Rojanathanes ◽  
Tanatorn Khotavivattana
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Anticancer Agent ◽  
Drug Loading ◽  
Calcium Citrate ◽  
Colorectal Cancer Cell Lines ◽  
Triazine Derivatives ◽  
Further Development ◽  
Derivatives Of ◽  
Potential Use

Twelve derivatives of biguanide-derived 1,3,5-triazines, a promising class of anticancer agent, were synthesised and evaluated for their anticancer activity against two colorectal cancer cell lines—HCT116 and SW620. 2c and 3c which are the derivatives containing o-hydroxyphenyl substituents exhibited the highest activity with IC50 against both cell lines in the range of 20–27 µM, which is comparable to the IC50 of cisplatin reference. Moreover, the potential use of the calcium citrate nanoparticles (CaCit NPs) as a platform for drug delivery system was studied on a selected 1,3,5-triazine derivative 2a. Condition optimisation revealed that the source of citrate ions and reaction time significantly influence the morphology, size and %drug loading of the particles. With the optimised conditions, “CaCit-2a NPs” were successfully synthesised with the size of 148 ± 23 nm and %drug loading of up to 16.3%. Furthermore, it was found that the release of 2a from the synthesised CaCit-2a NPs is pH-responsive, and 2a could be control released under the acidic cancer environment. The knowledge from this study is perceptive for further development of the 1,3,5-triazine-based anticancer drugs and provide the platform for the incorporation of other drugs in the CaCit NPs in the future.

tert-Amino effect in heterocyclic chemistry. Synthesis of hydrogenated spiro derivatives of quinolines

2004 ◽  
Vol 53 (6) ◽  
pp. 1240-1247 ◽  
Author(s):  
E. V. D"yachenko ◽  
T. V. Glukhareva ◽  
E. F. Nikolaenko ◽  
A. V. Tkachev ◽  
Yu. Yu. Morzherin
Keyword(s):  
Heterocyclic Chemistry ◽  
Spiro Derivatives ◽  
Derivatives Of

scholarly journals SYNTHESIS AND ANTIMICROBIAL EVALUATION OF QUINAZOLINONE PEPTIDE DERIVATIVES

2017 ◽  
Vol 10 (16) ◽  
pp. 7 ◽  
Author(s):  
Bhupinder Kapoor ◽  
Arshid Nabi ◽  
Reena Gupta ◽  
Mukta Gupta
Keyword(s):  
Antibacterial Activity ◽  
Amino Acid ◽  
Antimicrobial Agents ◽  
Methyl Esters ◽  
Standard Drug ◽  
Amino Acid Peptide ◽  
Chemical Structures ◽  
1H Nuclear Magnetic Resonance ◽  
Peptide Derivatives ◽  
Derivatives Of

  Objective: The increased microbial resistance against commercially available drugs initiated the development of novel and safe antimicrobial agents in last few decades. In this view, a series of amino acid/dipeptide derivatives of quinazolin-3(4H)-one was synthesized and was evaluated for their antimicrobial potential.Method: Synthesis of amino acid/peptide derivatives were carried out by coupling 5-(2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl)-2-hydroxy benzoic acid with amino acid/dipeptide methyl esters in the presence of dicyclohexylcarbodiimide and N-methylmorpholine. The chemical structures of synthesized compounds were characterized by 1H nuclear magnetic resonance and infrared spectroscopy and were screened for antibacterial activity by disc diffusion method.Results: All the synthesized derivatives exhibited moderate to significant antibacterial activity against both Gram-positive and Gram-negative bacteria. The potency of compound 5d was comparable to standard drug ciprofloxacin in all the strains of bacteria used. The compound 5a was found to be more active against Streptococcus pyogenes and Staphylococcus aureus while compound 5c against Pseudomonas aeruginosa and Escherichia coli. Conclusion: Peptide derivatives of quinazolinone are promising antimicrobial agent and can be used for the synthesis of other novel compounds.

scholarly journals Microbial Transformations of Isophorone by Alternaria alternata and Neurospora crassa

2013 ◽  
Vol 8 (1) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Ismail Kiran ◽  
Özge Özşen ◽  
Turgay Çelik ◽  
Semra İlhan ◽  
Bükay Yenice Gürsu ◽  
...  
Keyword(s):  
Neurospora Crassa ◽  
Alternaria Alternata ◽  
Antimicrobial Agents ◽  
Antimicrobial Activities ◽  
Anti Oxidant ◽  
Agar Dilution ◽  
Important Field ◽  
Pharmacology And Toxicology ◽  
Derivatives Of

Isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), a monoterpene, and the structurally related 1,8-cineole and camphor, have demonstrated a protective effect against cancer, biological activity against a variety of microorganisms, and anti-oxidant properties. The derivatization of isophorone is, therefore, an important field of xenobiochemistry, pharmacology and toxicology. The aim of this study was to obtain derivatives of isophorone through microbial biotransformation and evaluate the biotransformation metabolites as potential antimicrobial agents. Incubation of isophorone with the fungi Alternaria alternata and Neurospora crassa afforded 4α-hydroxy- and 7-hydroxy-isophorone as transformation metabolites. The antimicrobial activities of isophorone and the metabolites were evaluated in vitro both by using agar dilution and microdilution methods. However, no significant antibacterial activity was observed when compared with those of standard substances.

scholarly journals Microwave Assisted Synthesis and Antimicrobial Evaluation of Schiff Bases of Indole-3-aldehyde

2011 ◽  
Vol 8 (1) ◽  
pp. 305-311 ◽  
Author(s):  
Priyanka Kamaria ◽  
N. Kawathekar ◽  
Prerna Chaturvedi
Keyword(s):  
Schiff Bases ◽  
Antimicrobial Agents ◽  
Microwave Assisted Synthesis ◽  
Bacterial Strains ◽  
Mass Spectral Analysis ◽  
Gram Positive ◽  
Gram Negative ◽  
Mass Spectral ◽  
Microwave Assisted ◽  
Antimicrobial Evaluation

In order to develop new antimicrobial agents, a series of Schiff bases of indole-3-aldehyde were synthesized by microwave assisted synthesis by takingDMFas solvent and evaluated for their antimicrobial activity. All the synthesized compounds were characterized byIR,1HNMRand mass spectral analysis. All compounds were tested against five gram positive and five gram negative bacterial strains and one fungal strain. All compounds exhibited better activity against gram positive strains than against gram negative strains and the compounds were found more active againstS.aureusandB.subtilis.

scholarly journals Comparative In Vitro Activities of AC98-6446, a Novel Semisynthetic Glycopeptide Derivative of the Natural Product Mannopeptimycin α, and Other Antimicrobial Agents against Gram-Positive Clinical Isolates

2004 ◽  
Vol 48 (3) ◽  
pp. 739-746 ◽  
Author(s):  
Peter J. Petersen ◽  
T. Z. Wang ◽  
Russell G. Dushin ◽  
Patricia A. Bradford
Keyword(s):  
Natural Product ◽  
Bactericidal Activity ◽  
Antimicrobial Agents ◽  
Marked Decrease ◽  
Gram Positive ◽  
Novel Structure ◽  
Resistant Strains ◽  
Vancomycin Resistant ◽  
Further Development

ABSTRACT AC98-6446 is a novel semisynthetic cyclic glycopeptide antibiotic related to the natural product mannopeptimycin α (AC98-1). In the present study the activity of AC98-6446 was evaluated against a variety of recent clinical gram-positive pathogens including multiply resistant strains. AC98-6446 demonstrated similar potent activities against methicillin-susceptible and methicillin-resistant staphylococci and glycopeptide-intermediate staphylococcal isolates (MICs at which 90% of isolates are inhibited [MIC90s], 0.03 to 0.06 μg/ml). AC98-6446 also demonstrated good activities against both vancomycin-resistant and -susceptible strains of enterococci (MIC90s, 0.12 and 0.25 μg/ml, respectively) as well as against streptococcal strains (MIC90s, ≤ 0.008 to 0.03 μg/ml). AC98-6446 demonstrated bactericidal activity in terms of the reduction in the viable counts (>3 log10 CFU/ml) of staphylococcal and streptococcal isolates and a marked decrease in the viable counts of most enterococcal strains (from 0.2 to 2.5 log10 CFU/ml). Unlike vancomycin, which demonstrates time-dependent killing, AC98-6446 demonstrated concentration-dependent killing. The potent activity, novel structure, and bactericidal activity demonstrated by AC98-6446 make it an attractive candidate for further development.

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