Synthesis and Antimicrobial Activity of Some New 3,5-Disubstituted Pyrazoles and Isoxazoles

Reddy, Simha Pulla; Gudi, Yamini; Sowmya, Donthamsetty V; Padmavathi, V.; Padmaja, A.

doi:10.4172/2161-0444.1000483

Cited by 5 publications

(3 citation statements)

References 11 publications

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“…It is known that isoxazoles and their derivatives exhibit only moderate activity against Pseudomonas aeruginosa and are not active at all against Bacillus subtilis. [ 46–48 ] The starting silatrane 1 , mono‐isoxazole‐linked silatranes 3d‐f and bis‐isoxazole‐linked silatranes 4d‐f were chosen for preliminary screening of antimicrobial activity against bacterial strains of Gram‐positive Enterococcus durans B‐603, Bacillus subtilis B‐407 and Gram‐negative Escherichia coli B‐1238, Pseudomonas aeruginosa RPO1. The results of the antimicrobial activity of the tested silatranes are shown in Table 6.…”

Section: Resultsmentioning

confidence: 99%

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Адамович

Kondrashov

Ushakov

et al. 2020

Applied Organom Chemis

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A new family of mono‐ (3a‐h) and bis‐ (4a‐g) isoxazole‐bridged silatranes has been synthesized by the reaction of 3‐aminopropylsilatrane (1) and 3‐substituted 5‐chloro‐methylisoxazoles (2a‐h). The structure of the isoxazole‐silatrane hybrids is characterized by elemental analysis, FT‐IR, UV, NMR (1H, 13C,29Si and 15N) spectroscopy, high‐resolution mass spectrometry, and X‐ray diffraction analysis. The in silico ADME (absorption, distribution, metabolism, excretion) assessment reveals that properties of mono‐adducts (3a‐h) are similar to those of drugs obeyed to the Lipinski's rule. The calculated screening of potential pharmacological activity profiles (in silico PASS program) of isoxazole‐silatranes shows that all synthesized compounds (both mono‐ and bis‐substituted) may have high antitumor action, unlike starting isoxazoles. The preliminary screening of the synthesized silatranes for antimicrobial activity against Enterococcus durans, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa indicates that all test samples are active only against gram‐positive microorganisms. Silatrane 3f displays minimal inhibitory concentration (MIC 12.5 and 6.2 μg ml−1) against E. durans and B. subtilis as compared with standard drug gentamicin (MIC 25 and 50 μg ml−1).

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Section: Resultsmentioning

confidence: 99%

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Адамович

Kondrashov

Ushakov

et al. 2020

Applied Organom Chemis

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“…Furthermore, isoxazole derivatives possess various biological activities such as anti-inflammatory [ 21 ], antileishmanial [ 22 ], trypanocidal [ 23 ], antimicrobial [ 24 , 25 ] and antiviral ( Figure 2 , 2-C [ 26 ], 2-D [ 27 ]).…”

Section: Introductionmentioning

confidence: 99%

Design, Microwave-Assisted Synthesis and In Silico Prediction Study of Novel Isoxazole Linked Pyranopyrimidinone Conjugates as New Targets for Searching Potential Anti-SARS-CoV-2 Agents

et al. 2021

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A series of novel naphthopyrano[2,3-d]pyrimidin-11(12H)-one containing isoxazole nucleus 4 was synthesized under microwave irradiation and classical conditions in moderate to excellent yields upon 1,3-dipolar cycloaddition reaction using various arylnitrile oxides under copper(I) catalyst. A one-pot, three-component reaction, N-propargylation and Dimroth rearrangement were used as the key steps for the preparation of the dipolarophiles3. The structures of the synthesized compounds were established by 1H NMR, 13C NMR and HRMS-ES means. The present study aims to also predict the theoretical assembly of the COVID-19 protease (SARS-CoV-2 Mpro) and to discover in advance whether this protein can be targeted by the compounds 4a–1 and thus be synthesized. The docking scores of these compounds were compared to those of the co-crystallized native ligand inhibitor (N3) which was used as a reference standard. The results showed that all the synthesized compounds (4a–l) gave interesting binding scores compared to those of N3 inhibitor. It was found that compounds 4a, 4e and 4i achieved greatly similar binding scores and modes of interaction than N3, indicating promising affinity towards SARS-CoV-2 Mpro. On the other hand, the derivatives 4k, 4h and 4j showed binding energy scores (−8.9, −8.5 and −8.4 kcal/mol, respectively) higher than the Mpro N3 inhibitor (−7.0 kcal/mol), revealing, in their turn, a strong interaction with the target protease, although their interactions were not entirely comparable to that of the reference N3.

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“…The scope of heterocycles has been more recently widened with the development of the 1,3‐dipolar cycloaddition between an alkyne and a nitrile oxide, leading to a 1,2 isoxazole ring. The latter enabled therapeutic applications, such as analgesic, anti‐inflammatory,, Anti‐depressant,, and antibacterial, uses, among many others . Moreover, peptides are generally highly flexible; this feature decreases their ability to adopt a specific bioactive conformation and hampers their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Solid‐Phase Synthesis of Peptide Analogues Containing 3,4‐ or 3,5‐Disubstituted Isoxazole as s‐cis or s‐trans Peptide Bond Mimics

2019

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A method for regioselective solid‐phase synthesis of disubstituted peptidoisoxazoles is reported. Improved conditions for the synthesis of 3,5‐disubstituted isoxazoles (mimicking s‐trans peptide bond) without metal catalysts were implemented. New conditions enabling the synthesis of 3,4‐disubstituted isoxazoles (mimicking s‐cis peptide bond) using ruthenium catalysts were developed. This study provides a means for the regioselective preparation of new libraries of peptidomimetic molecules containing an isoxazole moiety within the backbone.

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Synthesis and Antimicrobial Activity of Some New 3,5-Disubstituted Pyrazoles and Isoxazoles

Cited by 5 publications

References 11 publications

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Isoxazole derivatives of silatrane: synthesis, characterization, in silico ADME profile, prediction of potential pharmacological activity and evaluation of antimicrobial action

Design, Microwave-Assisted Synthesis and In Silico Prediction Study of Novel Isoxazole Linked Pyranopyrimidinone Conjugates as New Targets for Searching Potential Anti-SARS-CoV-2 Agents

Regioselective Solid‐Phase Synthesis of Peptide Analogues Containing 3,4‐ or 3,5‐Disubstituted Isoxazole as s‐cis or s‐trans Peptide Bond Mimics

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