Synthesis, Biological Activity and DFT Studies of 1,3,4-oxadiazole Ring in Combination with Pyridinium Salt DOI

Mohammad H. Rababa,

Majd M. Alsaleh,

Alaa A. Abusamhadaneh

et al.

Current Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(1), P. 62 - 70

Published: Jan. 1, 2023

Aims: In this study, the synthesis and biological activity of new 1,3,4-oxadiazole derivatives will be discussed. Background: Microbial contagion via different bacterial strains discomposes healthcare system globally. 2019 E. coli, S. aureus, K. pneumoniae, pneumoniae were reported as most bacteremia deaths causes. Over time, bacteria develop ways to overcome antibiotic activity, causing multidrug resistant (MDR). The MDR is considered one biggest concerns scientists worldwide due its direct effect on patients' lives. As a result, developing drugs has become imperative for protect human life. Objective: Developing water soluble antibacterial from cheap commercially available materials. Methods: Microdilution Assay Antimicrobial potential was performed based experimental procedure with slight modifications. Briefly, chemical preparations serially diluted (2-fold) ten times Muller Hinton broth. Well number eleven negative control growth, while well twelve contained nutrient broth only used positive growth. achieved concentrations solutions 10 mg/mL 9 μg/mL. A serial two-fold dilution DMSO prepared ensure that antimicrobial not DMSO. Moreover, blank or background each final concentration in (except control) adjusted 0.75 × 106 CFU/ml. After inoculation bacteria, plates covered incubated overnight at 37oC 24 hours. then scanned an enzyme-linked immunosorbent assay (ELISA) reader 600 Nano moles examine density. lowest did allow any visible microbial growth test minimal inhibitory (MIC), which further confirmed by culturing (MIC) Henton agar incubating twenty-four molecular geometries compounds 4a, 4e, 4j, 4p optimized B3LYP/6-311+G(d,p) level theory using DFT calculations. Results: examination results show compound 4j interesting against faecium MIC value However, it found have low E.coli 625 On other hand, 4e showed very good 78 μg/mL 312 structural properties investigated density functional (DFT) biologically active gas phase B3LYP method 6-31+G(d,p) bases set. resulting ground-state structures take V shape two conjugated are connected methylene group. electrostatic map (MEP) calculated indicate that, intense blue region largest distributed over pyridinium ring, indicates binding chloride ion.

Language: Английский

Enantioselective 1,6-Addition of β-Ketoester Enolates to In Situ Generated para-Quinone Methides Enabled by Cooperative Palladium and Brønsted Acid Catalysis DOI

Cornelius V. Gärtner,

Christoph Schneider

Organic Letters, Journal Year: 2023, Volume and Issue: 25(2), P. 416 - 420

Published: Jan. 10, 2023

We report herein an asymmetric cooperative process for the enantioselective 1,6-addition of β-ketoesters to in situ generated para-quinone methides with chiral Pd-aqua complexes as mixed Brønsted acid-base catalysts. Excellent yields, outstanding enantiocontrol, and good diastereoselectivity across a broad substrate range are highlights this transformation. The utility reaction is further demonstrated by facile scale up subsequent complexity-increasing modifications.

Language: Английский

Citations

5
Machine Learning and Quantum Calculation for Predicting Yield in Cu-Catalyzed P–H Reactions DOI Creative Commons
Youfu Ma, Xianwei Zhang, Lin Zhu

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(16), P. 5995 - 5995

Published: Aug. 10, 2023

The paper discussed the use of machine learning (ML) and quantum chemistry calculations to predict transition state yield copper-catalyzed P–H insertion reactions. By analyzing a dataset 120 experimental data points, was determined using density functional theory (DFT). ML algorithms were then applied analyze 16 descriptors derived from chemical product yield. Among studied, Support Vector Machine (SVM) achieved highest prediction accuracy 97%, with over 80% correlation in Leave-One-Out Cross-Validation (LOOCV). Sensitivity analysis performed on each descriptor, comprehensive investigation reaction mechanism conducted better understand characteristics. Finally, model used plans for design, demonstrating strong predictive performance subsequent validation.

Language: Английский

Citations

5
Photocatalytic properties of two new isostructural cobalt(II) and nickel(II) complexes having terphenyl-3,3″,4,4″-teteacarboxylic acid DOI

Weiyi Kang,

Wenxu Zhong,

Congzhu Li

et al.

Polyhedron, Journal Year: 2022, Volume and Issue: 228, P. 116158 - 116158

Published: Oct. 10, 2022

Language: Английский

Citations

8
Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids DOI Creative Commons
Bhaskar C. Das, Pratik Yadav, Sasmita Das

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(3), P. 1052 - 1052

Published: Jan. 20, 2023

Dearomative borylation of coumarins and chromenes via conjugate addition represents a relatively unexplored challenging task. To address this issue, herein, we report new general copper (I) catalyzed dearomative process to synthesize boron-containing oxacycles. In report, the coumarins, chromones, comprising functional groups, such as esters, nitriles, carbonyls, amides, has been achieved. addition, method generates different classes potential boron-based retinoids, including ones with oxadiazole anthocyanin motifs. The borylated oxacycles can serve suitable intermediates generate library compounds.

Language: Английский

Citations

4
Synthesis, Biological Activity and DFT Studies of 1,3,4-oxadiazole Ring in Combination with Pyridinium Salt DOI

Mohammad H. Rababa,

Majd M. Alsaleh,

Alaa A. Abusamhadaneh

et al.

Current Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(1), P. 62 - 70

Published: Jan. 1, 2023

Aims: In this study, the synthesis and biological activity of new 1,3,4-oxadiazole derivatives will be discussed. Background: Microbial contagion via different bacterial strains discomposes healthcare system globally. 2019 E. coli, S. aureus, K. pneumoniae, pneumoniae were reported as most bacteremia deaths causes. Over time, bacteria develop ways to overcome antibiotic activity, causing multidrug resistant (MDR). The MDR is considered one biggest concerns scientists worldwide due its direct effect on patients' lives. As a result, developing drugs has become imperative for protect human life. Objective: Developing water soluble antibacterial from cheap commercially available materials. Methods: Microdilution Assay Antimicrobial potential was performed based experimental procedure with slight modifications. Briefly, chemical preparations serially diluted (2-fold) ten times Muller Hinton broth. Well number eleven negative control growth, while well twelve contained nutrient broth only used positive growth. achieved concentrations solutions 10 mg/mL 9 μg/mL. A serial two-fold dilution DMSO prepared ensure that antimicrobial not DMSO. Moreover, blank or background each final concentration in (except control) adjusted 0.75 × 106 CFU/ml. After inoculation bacteria, plates covered incubated overnight at 37oC 24 hours. then scanned an enzyme-linked immunosorbent assay (ELISA) reader 600 Nano moles examine density. lowest did allow any visible microbial growth test minimal inhibitory (MIC), which further confirmed by culturing (MIC) Henton agar incubating twenty-four molecular geometries compounds 4a, 4e, 4j, 4p optimized B3LYP/6-311+G(d,p) level theory using DFT calculations. Results: examination results show compound 4j interesting against faecium MIC value However, it found have low E.coli 625 On other hand, 4e showed very good 78 μg/mL 312 structural properties investigated density functional (DFT) biologically active gas phase B3LYP method 6-31+G(d,p) bases set. resulting ground-state structures take V shape two conjugated are connected methylene group. electrostatic map (MEP) calculated indicate that, intense blue region largest distributed over pyridinium ring, indicates binding chloride ion.

Language: Английский

Citations

4