Synthesis and Antimicrobial Study of Novel 1‐Benzylated Water‐Soluble Isatin‐3‐hydrazones

Богданов, А. В.; Zaripova, Ilyuza F.; Voloshina, Alexandra D.; Sapunova, Аnastasiia S.; Кулик, Н. В.; Voronina, Julia K.; Миронов, В. Ф.

doi:10.1002/cbdv.201800088

Cited by 20 publications

(5 citation statements)

References 34 publications

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“…A Girard-type reagents’ strategy for improving the separation efficiency of carbonyl compounds is a well-established method in organic chemistry since 1936, and a lot of useful contribution toward the application of these reagents has been done in the 1940–1960s with particular emphasis on the isolation of natural products (mainly stereoids and alkaloids) as well as the synthesis of the water-soluble Girard hydrazones of pharmaceuticals. − Although Girard’s reagents constitute rather “old-fashioned” compounds, they are still willingly applied in various modern synthetic endeavors and analytical protocols. In this regard, Girard’s hydrazides play a crucial role in the preparation of various biologically active derivatives − and functional materials as well as the scavengers suitable for the isolation of natural products , and/or as derivatization agents auxiliary for the detection of organic analytes. − …”

Section: Resultsmentioning

confidence: 99%

From Waste to Value—Direct Utilization of α-Angelica Lactone as a Nonconventional Irreversible Acylating Agent in a Chromatography-Free Lipase-Catalyzed KR Approach toward sec-Alcohols

Poterała

Borowiecki

2021

ACS Sustainable Chem. Eng.

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Although the classical enzymatic kinetic resolutions (EKRs) are among the most important reactions in biocatalysis, the requirement of application of chromatographic purification technique, which is responsible for the generation of large amounts of waste organic solvents, is its major drawback. To minimize the environmental impact of such attempts and to address the current sustainability challenges, we decided to develop a novel EKR methodology, which relies on the usage of cheap, fully renewable, nontoxic, and irreversible acyl group donor reagent, namely, α-angelica lactone. The employed activated enol lactone-based acyl donor proved to be a versatile reagent enabling efficient and highly enantioselective (up to E ≫ 500) lipase-catalyzed resolution of a set of racemic sec-alcohols with up to >99% ee and near to quantitative isolation yields according to conversions achieved during the respective EKR procedure. Moreover, α-angelica lactone provided, in this case, an ability of fast and straightforward separation of the enzymatic reactions’ products via chromatography-free reactive liquid–liquid extraction (LLE) workup using either saturated aqueous sodium bisulfate in dimethylformamide (DMF) or Girard’s P reagent in a mixture of EtOH/AcOH (90:10, v/v), respectively. The NaHSO3/DMF LLE workup and the subsequent reisolation of the respective levulinate from the aqueous layer turned out to be less efficient than a separation with Girard’s P reagent. The selective LLE of optically active levulinate-Girard P-hydrazones from the respective alcohols and further hydrolysis of the respective hydrazides with diluted HClaq. could be performed with high levels of recovery of both EKR products isolated usually without loss of enantiomeric purity.

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Section: Resultsmentioning

confidence: 99%

From Waste to Value—Direct Utilization of α-Angelica Lactone as a Nonconventional Irreversible Acylating Agent in a Chromatography-Free Lipase-Catalyzed KR Approach toward sec-Alcohols

Poterała

Borowiecki

2021

ACS Sustainable Chem. Eng.

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“…[ 143 ] The introduction of benzyl group at the N‐1 position of indole moiety was also tolerated, as evidenced by the fact that hybrids 70a,b (MIC: 16.2–32.3 μM) were more potent than chloramphenicol (MIC: 193 μM) against S. aureus and B. cereus . [ 144 ] The activity of hybrids 71a–c (MIC: 3.12–6.25 μg/ml) was equal to that of ciprofloxacin (MIC: 3.12–6.25 μg/ml) against S. aureus , S. epidermidis , P. mirabilis , and E. coli , so these hybrids were potential prototypes for the discovery of novel antibacterial candidates. [ 145 ]…”

Section: Indole/isatin–imine Hybridsmentioning

confidence: 99%

Indole/isatin‐containing hybrids as potential antibacterial agents

Song

Bian

et al. 2020

Archiv der Pharmazie

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The emergence and worldwide spread of drug-resistant bacteria have already posed a serious threat to human life, creating the urgent need to develop potent and novel antibacterial drug candidates with high efficacy. Indole and isatin (indole-2,3-dione) present a wide structural and mechanistic diversity, so their derivatives possess various pharmacological properties and occupy a salient place in the development of new drugs. Indole/isatin-containing hybrids, which demonstrate a promising activity against a panel of clinically important Gram-positive and Gram-negative bacteria, are privileged scaffolds for the discovery of novel antibacterial candidates. This review, covering articles published between January 2015 and May 2020, focuses on the development and structure-activity relationship (SAR) of indole/isatincontaining hybrids with potential application for fighting bacterial infections, to facilitate further rational design of novel drug candidates.

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“…Several years ago, we first described the synthesis of a new type of water‐soluble isatin acylhydrazones, containing a quaternized nitrogen atom, with low toxicity and selective activity against Gram‐positive bacterial pathogens [24–31] . We showed that the most active derivatives of this series against Staphylococcus aureus ( S. aureus ) and Bacillus cereus ( B. cereus ) were hydrazones containing a sterically hindered phenolic fragment ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Isatin‐3‐acylhydrazones with Enhanced Lipophilicity: Synthesis, Antimicrobial Activity Evaluation and the Influence on Hemostasis System

Богданов

Voloshina

Sapunova

et al. 2022

Chemistry & Biodiversity

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Water‐soluble trialkylammonium isatin‐3‐hydrazone derivatives bearing phenolic substituent were easily synthesized with high yields. XRD studies confirmed the presence of these compounds as trans‐(Z)‐isomers in a crystal. It was shown that an increase in the lipophilicity of the cationic center leads to an increase in activity against Gram‐positive bacteria Staphylococcus aureus and Bacillus cereus, including methicillin‐resistant Staphylococcus aureus (MRSA) strains. The MIC values of all compounds turned out to be 2–100 times higher than the MIC of norfloxacin against the MRSA strains in the absence of hemo‐ and cytotoxicity. Antiaggregation and anticoagulation properties were in vitro better than for acetylsalicylic acid and sodium heparin drugs. It has been shown by UV spectroscopy and fluorescence microscopy that the mechanism of antimicrobial action of new acylhydrazones is associated with their ability to destroy the bacterial cell membrane.

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Synthesis and Antimicrobial Study of Novel 1‐Benzylated Water‐Soluble Isatin‐3‐hydrazones

Cited by 20 publications

References 34 publications

From Waste to Value—Direct Utilization of α-Angelica Lactone as a Nonconventional Irreversible Acylating Agent in a Chromatography-Free Lipase-Catalyzed KR Approach toward sec-Alcohols

From Waste to Value—Direct Utilization of α-Angelica Lactone as a Nonconventional Irreversible Acylating Agent in a Chromatography-Free Lipase-Catalyzed KR Approach toward sec-Alcohols

Indole/isatin‐containing hybrids as potential antibacterial agents

Isatin‐3‐acylhydrazones with Enhanced Lipophilicity: Synthesis, Antimicrobial Activity Evaluation and the Influence on Hemostasis System

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