Oximes of five-membered heterocyclic compounds with three and four heteroatoms 1. Synthesis and structure (review)

Абеле, Э.; Абеле, Р.; Lukevics, É.

doi:10.1007/s10593-008-0094-5

Cited by 6 publications

(3 citation statements)

References 52 publications

(59 reference statements)

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“…Then, compound 3 was converted to its oxime derivate (4) by refluxing with hydroxylamine hydrochloride (NH 2 OH.HCl) under alkaline conditions. The final compounds (5)(6)(7)(8)(9)(10)(11)(12) were synthesized by sodium salt reaction of 1-(naphthalene-2-yl)-2-(1Hpyrazol-1-yl)ethanone oxime (4) with various acyl chlorides (Figure 1). The structures of 5-12 were determined by IR, 1 H-NMR,…”

Section: Synthesis and Spectral Datamentioning

confidence: 99%

“…This work is licensed under the Creative Commons Attribution 4.0 International License Heterocyclic compounds have been in use in medicinal chemistry as basic structures in the development of active molecules, many of which contain pyrazoles or pyrazole substitutes [3][4][5][6]. In addition, several effective molecules also contain oxime and oxime ester groups [7,8]. For example, some 2-(3,5-dimethyl-1H-pyrazol-1-yl)-1-arylethanone derivatives are reported to be effective anticancer agents [8,9].…”

Section: Introductionmentioning

confidence: 99%

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Purpose: To synthesize a series of new 1-(2-naphthyl)-2-(1H-pyrazol-1-yl)ethanone oxime ester derivatives (5)(6)(7)(8)(9)(10)(11)(12) with potential anticancer properties, and to determine their cytotoxic effects in mouse fibroblast and human neuroblastoma cell lines. Methods: The title compounds were obtained through sodium salt reaction of 1-(naphthalene-2-yl)-2-(1H-pyrazol-1-yl)etanone oxime (4) with various acyl chlorides.

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confidence: 99%

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Synthesis and cytotoxicity studies on new pyrazolecontaining oxime ester derivatives

Karakurt¹,

Bozbey²,

Uslu³

et al. 2021

Trop. J. Pharm Res

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Purpose: To synthesize a series of new 1-(2-naphthyl)-2-(1H-pyrazol-1-yl)ethanone oxime ester derivatives (5-12) with potential anticancer properties, and to determine their cytotoxic effects in mouse fibroblast and human neuroblastoma cell lines. Methods: The title compounds were obtained through sodium salt reaction of 1-(naphthalene-2-yl)-2- (1H-pyrazol-1-yl)etanone oxime (4) with various acyl chlorides. The cytotoxic effects were evaluated by MTS colorimetric assay, while physicochemical descriptors were calculated using QikProp software. Results: Most of the compounds showed approximately 50 – 60 % inhibition against SH-SY5Y neuroblastoma cells at 100 μM. Of these, compound 7a was the most active combination with an IC50 value of 85.94 µM. The toxic effect of the compounds on mouse fibroblast cell line was insignificant (p < 0.05) even when the dose was increased. The calculated physicochemical properties of the compounds were within drug-like chemical space. Conclusion: The synthesized oxime ester derivatives with pyrazole ring exhibit selective toxicity to neuroblastoma cells without affecting healthy mouse fibroblast cells. The compounds proved to be druglike while their pharmacokinetic features were also encouraging, and were in line with in silico predictions.

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