Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers

Kosmalski, Tomasz; Studzińska, Renata; Redka, Małgorzata; Pluskota, Robert; Modzelewska-Banachiewicz, Bożena

doi:10.21577/0103-5053.20170055

Cited by 4 publications

(4 citation statements)

References 14 publications

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“…It seems possible to use the experimental parameter logk w-MeOH interchangeably with ALOGP and MLOGP. On the other hand, Kosmalski et al [ 18 ] obtained completely different results in terms of the correlation of the calculation parameters of lipophilicity and the experimental parameters for 1-(benzofuran-2-yl) ethan-1-one oxime and its substituted O-benzyl ethers. It was shown in this work that it is logk w-ACN that is better correlated with the calculation parameters.…”

Section: Discussionmentioning

confidence: 99%

Selected Drug-Likeness Properties of 2-Arylidene-indan-1,3-dione Derivatives—Chemical Compounds with Potential Anti-Cancer Activity

et al. 2021

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2-Arylidene-indan-1,3-done derivatives have very different properties, thanks to which they find various applications in science, medicine, and industry. Selected derivatives show antiviral, antibacterial, and anti-inflammatory activity. This paper presents a procedure for the synthesis of a series of indan-1,3-dione derivatives that present antiproliferative activity. The aim of the work was to develop a method of simple synthesis and purification, evaluate the fulfillment of the Lipiński’s and Veber’s rule, and determine the potential scope of application of the obtained series of compounds. The structure of the synthesized compounds was confirmed, and their lipophilicity was determined using experimental and computational methods. Their antiproliferative activity against selected cell lines was tested in accordance with the MTT protocol; the ability to bind to albumin was tested, and the parameters related to the toxicity of substances in silico were determined. The selected compounds which showed antiproliferative activity were strongly bound to albumin and, in most cases, met the Lipiński’s and Veber’s rule. Thus, the obtained results suggest that 2-arylidene-indan-1,3-done derivatives appear to be good candidates for drugs with a potential leading structure for further development.

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Section: Discussionmentioning

confidence: 99%

Selected Drug-Likeness Properties of 2-Arylidene-indan-1,3-dione Derivatives—Chemical Compounds with Potential Anti-Cancer Activity

et al. 2021

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“…Using the Reversed-Phase HPLC Technique [46,47] The HPLC experiments were performed on the Shimadzu HPLC system (Kyoto, Japan) equipped with solvent delivery pump LC-20AD, UV-VIS detector model SPD-20A, degasser model DGU-20A5, a column oven model CTO-20A, and a column Superspher ® 100 RP-18 (4 µm), Merck (Darmstadt, Germany). Methanol and water for HPLC from POCH (Gliwice, Poland) were used as solvents.…”

Section: Determination Of Lipophilicity Parametersmentioning

confidence: 99%

Lipophilic Studies and In Silico ADME Profiling of Biologically Active 2-Aminothiazol-4(5H)-one Derivatives

Redka,

Baumgart,

Kupczyk

et al. 2023

IJMS

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Pseudothiohydantoin derivatives have a wide range of biological activities and are widely used in the development of new pharmaceuticals. Lipophilicity is a basic, but very important parameter in the design of potential drugs, as it determines solubility in lipids, nonpolar solvents, and makes it possible to predict the ADME profile. The aim of this study was to evaluate the lipophilicity of 28 pseudothiohydantoin derivatives showing the inhibition of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) using chromatographic methods. Experimentally, lipophilicity was determined by reverse phase thin layer chromatography (RP-TLC) and reverse phase high-performance liquid chromatography (RP-HPLC). In both methods, methanol was used as the organic modifier of the mobile phase. For each 2-aminothiazol-4(5H)-one derivative, a relationship was observed between the structure of the compound and the values of the lipophilicity parameters (log kw, RM0). Experimental lipophilicity values were compared with computer calculated partition coefficient (logP) values. A total of 27 of the 28 tested compounds had a lipophilicity value < 5, which therefore met the condition of Lipinski’s rule. In addition, the in silico ADME assay showed favorable absorption, distribution, metabolism, and excretion parameters for most of the pseudothiohydantoin derivatives tested. The study of lipophilicity and the ADME analysis indicate that the tested compounds are good potential drug candidates.

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“…[1] Heterocyclic oxime ethers such as Oxicanazole are important antifungal drugs that are used in the treatment of mycosis. [2] Respective structure motifs are shown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Cesium Carbonate Catalyzed Oxa‐Michael Addition of Oximes to Acrylonitrile

et al. 2021

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We report the O-alkylation of oximes with Michael acceptors using Cs 2 CO 3 as the catalyst. The transformation proceeds stereospecifically with retention of the oxime configuration. Irradiation with visible light in the presence of diphenyl anthracene and cerium complexes affects the E to Z config-uration ratio of the oxime ether products, but a complete stereocontrol was not achieved. The operationally simple protocol allows the synthesis of various O-alkylated oxime products that are useful precursors for further chemical transformations.

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Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers

Cited by 4 publications

References 14 publications

Selected Drug-Likeness Properties of 2-Arylidene-indan-1,3-dione Derivatives—Chemical Compounds with Potential Anti-Cancer Activity

Selected Drug-Likeness Properties of 2-Arylidene-indan-1,3-dione Derivatives—Chemical Compounds with Potential Anti-Cancer Activity

Lipophilic Studies and In Silico ADME Profiling of Biologically Active 2-Aminothiazol-4(5H)-one Derivatives

Cesium Carbonate Catalyzed Oxa‐Michael Addition of Oximes to Acrylonitrile

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