Synthesis of new anticancer and anti-inflammatory isoxazolines and aziridines from the natural (-)-deltoin

Znati, Mansour; Debbabi, Meriem; Romdhane, Anis; Jannet, Hichem Ben; Bouajila, Jalloul

doi:10.1111/jphp.13013

Cited by 10 publications

(3 citation statements)

References 30 publications

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“…When it came to the human colon cell line HCT-116, compound 28 ( Figure 18 ) was the most effective (IC 50 = 3.3 µM), four times as effective as the parent chemical (IC 50 = 14.3 µM). This finding suggests that the introduction of the isoxazoline fraction yielded better anticancer potential [ 53 ].…”

Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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Isoxazoles and isoxazolines are five-membered heterocyclic molecules containing nitrogen and oxygen. Isoxazole and isoxazoline are the most popular heterocyclic compounds for developing novel drug candidates. Over 80 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antidiabetic, cardiovascular, and other activities, were reviewed. A review of recent studies on the use of isoxazoles and isoxazolines moiety derivative activities for natural products is presented here, focusing on the parameters that affect the bioactivity of these compounds.

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Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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“…Sesquiterpene lactones, coumarin derivatives, steroids were obtained from representatives of the Astaraceae and Apiaceae and other families, which are widely used in medical practice. Representatives of these compounds have different pharmacological activity, are used as an anesthetic, anticoagulant, capillary strengthening, anticarcinogenic, anti-inflammatory and choleretic agent, and so on [Arzamastsev, 2004;Okamoto et al, 2005;Kang et al, 2009;Feng et al, 2010;Anand et al, 2012;Venugopala et al, 2013;Kermani et al, 2016;Zohu et al, 2017;Znati et al, 2018].…”

Section: Sesquiterpene Lactones In the Aerial Part Of Artemisia Maritima Lmentioning

confidence: 99%

Sesquiterpene lactones in the aerial part of Artemisia maritima L.

Serkerov¹

2019

plantfungalres

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Three substances are separated from the above-ground part of Artemisia maritima L. by column chromatography method in an individual state: C 15 H 18 O 3 with a m.p. of 171-172°C (substance 1), C 15 H 18 O 3 with a melting temperature of 130-131°C (substance 2), C 15 H 18 O 4 with a melting point of 201-202°С (substance 3), which are identified as α-santonin, glabellin and artemisin on the basis of 1 H NMR spectra and direct comparison of IR spectra.

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“…Reactions between nitrile N-oxides and alkenes obtain ∆ 2 -isoxazolines, which are widely spread out as biological and pharmacological substances. They exhibit, for example, an antibacterial [11] and an antiviral [12] effect; therefore, they can be used in medicine as anti-inflammatory [13,14] and analgesic drugs [15]. The most popular medicines containing isoxazolines rings in their structures are Zonisamid and Risperidone [16].…”

Section: Introductionmentioning

confidence: 99%

Application of β-Phosphorylated Nitroethenes in [3+2] Cycloaddition Reactions Involving Benzonitrile N-Oxide in the Light of a DFT Computational Study

Zawadzińska

Kula

2021

Organics

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The regiochemistry of [3+2] cycloaddition (32CA) processes between benzonitrile N-oxide 1 and β-phosphorylated analogues of nitroethenes 2a–c has been studied using the Density Functional Theory (DFT) at the M062X/6-31+G(d) theory level. The obtained results of reactivity indices show that benzonitrile N-oxide 1 can be classified both as a moderate electrophile and moderate nucleophile, while β-phosphorylated analogues of nitroethenes 2a–c can be classified as strong electrophiles and marginal nucleophiles. Moreover, the analysis of CDFT shows that for [3+2] cycloadditions with the participation of β-phosphorylatednitroethene 2a and β-phosphorylated α-cyanonitroethene 2b, the more favored reaction path forms 4-nitro-substituted Δ2-isoxazolines 3a–b, while for a reaction with β-phosphorylated β-cyanonitroethene 2c, the more favored path forms 5-nitro-substituted Δ2-isoxazoline 4c. This is due to the presence of a cyano group in the alkene. The CDFT study correlates well with the analysis of the kinetic description of the considered reaction channels. Moreover, DFT calculations have proven the clearly polar nature of all analyzed [3+2] cycloaddition reactions according to the polar one-step mechanism.

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Synthesis of new anticancer and anti-inflammatory isoxazolines and aziridines from the natural (-)-deltoin

Abstract: Some analogues have been found more bioactive than deltoin 1. Their activity has been related to the nature of the added heterocycles. It would be interesting to evaluate their in-vivo activity.

Cited by 10 publications

References 30 publications

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Sesquiterpene lactones in the aerial part of Artemisia maritima L.

Application of β-Phosphorylated Nitroethenes in [3+2] Cycloaddition Reactions Involving Benzonitrile N-Oxide in the Light of a DFT Computational Study

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