Synthesis and luminescent properties of 2-[2′-acyl(benzoyl)oxyphenyl]-5-(4″-nonylphenyl)-1,3,4-oxadiazole

Михайлов, И. Е.; Попов, Л. Д.; Vikrishchuk, N. I.; Beldovskaya, A. D.; Revinskii, Y.-U. V.; Душенко, Г. А.

doi:10.1134/s1070363215010363

Cited by 18 publications

(2 citation statements)

References 7 publications

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“…Therefore, the pyridine‐mediated acylation of hybrid 4c with the appropriate acyl chlorides 12a,b was conducted. [ 74 ] The reaction mixture was stirred in dichloromethane at room temperature (RT) for 3 h to produce the corresponding 1,3,4‐oxadiazole derivatives 4j and 4k , linked to acetoxy and benzoyloxy units, in 72% and 78% yields, respectively (see Scheme 7 and Section 4).…”

Section: Resultsmentioning

confidence: 99%

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Sanad

Mekky

Ahmed

2022

Archiv der Pharmazie

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A new series of pyrrole-linked mono-and bis(1,3,4-oxadiazole) hybrids, attached to various arene units, was prepared using a two-step tandem protocol. Therefore, a benzohydrazide derivative was condensed with the appropriate aldehydes in ethanol at 80°C for 60-150 min to give the corresponding N-(benzoylhydrazones). Without isolation, the previous intermediates underwent intramolecular oxidative cyclization in dimethyl sulfoxide at 180°C for 90-200 min in the presence of chloramine trihydrate to afford the target hybrids. The cytotoxicity of all hybrids was examined in vitro against the MCF-7, HEPG2, and Caco2 cell lines. Arene-linked hybrids 4i and 4j, attached to p-nitro and pacetoxy units, were the most potent ones, with IC 50 values ranging from 5.47 to 8.80 and 12.75 to 21.22 μM, respectively, when tested on the above cell lines. At the tested concentrations of 5 and 7.5 μM, hybrid 4i inhibited thymidylate synthase (TS) with the best inhibition percentages of 72.3 and 91.3, whereas hybrid 4j displayed comparable inhibitory activity to the reference pemetrexed. Hybrid 4j had inhibition percentages of 62.7 and 82.6, whereas pemetrexed had inhibition percentages of 59.2 and 80.2, respectively. The capability of hybrids 4i and 4j as potential TS inhibitors is supported by molecular docking studies, while SwissADME predicts their efficacy as drug-like scaffolds.

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Section: Resultsmentioning

confidence: 99%

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Sanad

Mekky

Ahmed

2022

Archiv der Pharmazie

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“…These compounds have diverse biological activity [1] and are extensively used in various fields of medicinal chemistry [2] and pesticide chemistry [3]. Also, they possess interesting spectral luminescent properties making them suitable for the preparation of widely demanded organic [4][5][6][7] and metal complex-based [8,9] phosphors.…”

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Spectral Luminescent Properties of 2-Aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles

et al. 2018

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Abstract-2-Aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles were synthesized by cyclization reaction of benzoylbenzohydrazides in SOCl 2 , and their spectral luminescent properties were studied. The oxadiazoles containing phenyl or o-methoxyphenyl substituents in the position 2 were shown to luminesce with a high quantum yield in polar and nonpolar solvents. The replacement of these substituents by 2-hydroxyphenyl group led to oxadiazole intensely emitting only in highly polar aprotic DMSO.Keywords: 2,5-diaryl-1,3,4-oxadiazoles, luminescence, luminescence quantum yield, organic phosphors ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 2, pp. 338-341. © Pleiades Publishing, Ltd., 2018. Original Russian Text © I.E. Mikhailov, Yu.M. Artyushkina, G.A. Dushenko, O.I. Mikhailova, Yu.V. Revinskii, V.I. Minkin, 2018, published in Zhurnal Obshchei Khimii, 2018 1,3,4-Oxadiazoles and their derivatives belong to one of the most intensively studied classes of fivemembered nitrogen-containing heterocycles characterized by good synthetic accessibility and high structural variability, as well as by wide range of practical applicability. These compounds have diverse biological activity [1] and are extensively used in various fields of medicinal chemistry [2] and pesticide chemistry [3]. Also, they possess interesting spectral luminescent properties making them suitable for the preparation of widely demanded organic [4][5][6][7] and metal complex-based [8,9] phosphors. LETTERS TO THE EDITORFor expanding the range of compounds of this class and for studying their spectral luminescent properties we applied here the reaction of hydrazides 1a-1c with 2,6-dimethoxybenzoic acid chloride in the presence of triethylamine to obtain benzoylbenzohydrazides 2a-2c whose subsequent cyclization with thionyl chloride led to 2-aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles 3a-3c (Scheme 1).In the absorption spectra of oxadiazoles 3a-3c the maximum of the long-wave band due to π→π* electron transitions is observed within the 256-316 nm range, consistent with their benzenoid structure. The luminescence spectra of oxadiazole 3b in isooctane, toluene, and acetonitrile contain two bands: a shortwave band (λ m fl ax 353-378 nm, φ 0.001-0.012) which has a normal Stokes shift (3019-4992 cm

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New Arene and/or Heteroarene‐Linked 1,3,4‐Oxadiazoles: Synthesis of Potential Methicillin‐Resistant Staphylococcus aureus and Vancomycin‐Resistant Enterococcus Inhibitors

Mekky,

Abdelbaath,

Abdelbaath

et al. 2024

ChemistrySelect

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Bacterial infections, particularly those associated with methicillin‐resistant Staphylococcus aureus (MRSA) and vancomycin‐resistant Enterococcus (VRE), threaten public health and economies, with rising antibiotic resistance resulting in more deaths yearly. In this study, we investigated the bacterial inhibitory activity of some new 1,3,4‐oxadiazoles prepared, in good yields, using a two‐step tandem protocol. Therefore, the appropriate N‐benzoylhydrazones were prepared first, then, without isolation, underwent oxidative‐cyclization in the presence of chloramine trihydrate. More 4‐acyloxyphenyl‐linked 1,3,4‐oxadiazoles were prepared by the pyridine‐mediated acylation of 2‐(4‐hydroxyphenyl)‐1,3,4‐oxadiazoles with the appropriate acyl chlorides. Some new products demonstrated good activity, particularly against S. aureus and Enterococcus faecalis strains. The 4‐(5‐(furan‐2‐yl)‐1,3,4‐oxadiazol‐2‐yl)phenyl acetate showed comparable antibacterial activity to ciprofloxacin, with MIC/MBC values up to 3.6/7.2 µM against the previous strains. Moreover, it demonstrated good inhibitory activity against different MRSA and VRE strains when compared to linezolid. It had MIC/MBC values of 7.2/14.4 and 14.4/57.8 µM against MRSA and VRE strains, respectively.

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Synthesis and luminescent properties of 2-[2′-acyl(benzoyl)oxyphenyl]-5-(4″-nonylphenyl)-1,3,4-oxadiazole

Cited by 18 publications

References 7 publications

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Tandem synthesis, cytotoxicity, and in silico study of new 1,3,4‐oxadiazoles as potential thymidylate synthase inhibitors

Spectral Luminescent Properties of 2-Aryl-5-(2,6-dimethoxyphenyl)-1H-1,3,4-oxadiazoles

New Arene and/or Heteroarene‐Linked 1,3,4‐Oxadiazoles: Synthesis of Potential Methicillin‐Resistant Staphylococcus aureus and Vancomycin‐Resistant Enterococcus Inhibitors

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