Synthesis and antimicrobial evaluation of isoxazole-substituted 1,3,4-oxadiazoles

Marri, Srinivas; Kakkerla, Ramu; Krishna, M. P. S. Murali; Rajam, Manchikatla Venkat

doi:10.1515/hc-2018-0137

Cited by 15 publications

(3 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Obviously, this fact is crucial and is fully consistent with the results of other studies on antibacterial activities. [ 25,49 ] It is noteworthy that the growth of spore microorganisms ( Bacillus subtilis ) is suppressed to a higher degree than non‐spore ones ( Enterococcus durans ). A standard aminoglycoside antibiotic, Gentamicin, was used for the comparison.…”

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

View full text Add to dashboard Cite

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).

show abstract

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

View full text Add to dashboard Cite

show abstract

“…Taking into account the high potential of nitro-functionality [24][25][26] and silatrane scaffold in medicinal chemistry, in the work reported here, 2-hydoxy-5-nitrobenzaldehyde was used as a precursor to synthesize a new silatrane imine derivative. The reported nitro silatrane derivative was structurally characterized by spectral and single crystal Xray diffraction analysis and screened for its photophysical properties, hydrolytic stability, protein-binding ability, muco-adhesivity, antitumor, and antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Chemical Attachment of 5-Nitrosalicylaldimine Motif to Silatrane Resulting in an Organic–Inorganic Structure with High Medicinal Significance

Zaltariov¹,

Turtoi

Peptanariu³

et al. 2022

Pharmaceutics

View full text Add to dashboard Cite

Two chemical motifs of interest for medicinal chemistry, silatrane as 1-(3-aminopropyl) silatrane (SIL M), and nitro group attached in position 5 to salicylaldehyde, are coupled in a new structure, 1-(3-{[(2-hydroxy-5-nitrophenyl)methylidene]amino}propyl)silatrane (SIL-BS), through an azomethine moiety, also known as a versatile pharmacophore. The high purity isolated compound was structurally characterized by an elemental, spectral, and single crystal X-ray diffraction analysis. Given the structural premises for being a biologically active compound, different specific techniques and protocols have been used to evaluate their in vitro hydrolytic stability in simulated physiological conditions, the cytotoxicity on two cancer cell lines (HepG2 and MCF7), and protein binding ability—with a major role in drug ADME (Absorption, Distribution, Metabolism and Excretion), in parallel with those of the SIL M. While the latter had a good biocompatibility, the nitro-silatrane derivative, SIL-BS, exhibited a higher cytotoxic activity on HepG2 and MCF7 cell lines, performance assigned, among others, to the known capacity of the nitro group to promote a specific cytotoxicity by a “activation by reduction” mechanism. Both compounds exhibited increased bio- and muco-adhesiveness, which can favor an optimized therapeutic effect by increased drug permeation and residence time in tumor location. Additional benefits of these compounds have been demonstrated by their antimicrobial activity on several fungi and bacteria species. Molecular docking computations on Human Serum Albumin (HSA) and MPRO COVID-19 protease demonstrated their potential in the development of new drugs for combined therapy.

show abstract

“…Compound 55 found to be most active (ZOI = 69.5-80.5 mm) against most of the tested fungal strains among synthesized derivatives (Table24). Overall active compounds(54)(55)(56) showed excellent activity as compared to standard drugs Clotrimazole and Ciprofloxacin (Table23, 24)[66]. S. aureus, E. coli and P. aeruginosa (MIC range = 12.5-25 µg/mL) except 57 against E. coli (MIC = 50 µg/mL)…”

mentioning

confidence: 99%

Antimicrobial Activity and Sar of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives

Kumar

Narang

Devgun

et al. 2022

JASR

View full text Add to dashboard Cite

1,3,4-oxadiazole is a five membered heterocyclic aromatic moiety, present in a number of antimicrobial agents. 2,5- disubstituted 1,3,4-oxadiazole derivatives have shown broad spectrum of antibacterial and antifungal activities. Many scientific groups have synthesized and screened their antimicrobial potential. Reported activity data showed that some 1,3,4-oxadiazole derivatives exhibited better activity than already known antibiotics. Hence, they can be used as lead for development of promising antimicrobial agents. In present review, antimicrobial activities and SAR of 2,5-disubstituted 1,3,4-oxadiazole derivatives reported by different research groups in last ten years have been summarized.

show abstract

Synthesis and antimicrobial evaluation of isoxazole-substituted 1,3,4-oxadiazoles

Cited by 15 publications

References 25 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

Chemical Attachment of 5-Nitrosalicylaldimine Motif to Silatrane Resulting in an Organic–Inorganic Structure with High Medicinal Significance

Antimicrobial Activity and Sar of 2,5-Disubstituted 1,3,4-Oxadiazole Derivatives

Contact Info

Product

Resources

About