Chemical profiling, cytotoxic activities through apoptosis induction in human fibrosarcoma and carcinoma cells, and molecular docking of some 1,2,3-triazole-isoxazoline hybrids using the eugenol as a precursors

Oubella, Ali; Taia, Abdelmaoujoud; Byadi, Said; Lahcen, Marouane Ait; Bimoussa, Abdoullah; Essaber, Mohamed; Podlipnik, Črtomir; Morjani, Hamid; Itto, My Youssef Ait; Aatif, Abdeljalil

doi:10.1080/07391102.2022.2037466

Cited by 15 publications

(9 citation statements)

References 57 publications

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“…According to preliminary structural investigations, the simultaneous presence of 1,2,3-triazole and isoxazole produced stronger anticancer effects. Follow-up studies showed that the most potent compound 33a , induced apoptosis through the activation of caspase-3/7, leading to cell cycle arrest in A-549 cancer cells in the G2/M phase [ 57 ].…”

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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“…In parallel reports, the procedure of obtaining triazole-eugenol-isoxazoline- p -chlorophenyl hybrids involving 1,3-DP cycloaddition of p -ClC 6 H 4 CNO to aryltriazole-allyleugenol-type dipolarophiles was described— Scheme 156 [ 165 , 166 ].…”

Section: Syntheses Of Substituted 2-isoxazolines Via 13-dp Cycloaddit...mentioning

confidence: 99%

“…Antiproliferative activity tests disclosed that some of the obtained derivatives showed significant cytotoxicity against fibrosarcoma and lung and breast carcinoma cell lines [ 166 ]. Interestingly, one of the hybrid compounds (R = Bn) showed the highest anticancer activity against all tested tumor cell lines, with IC 50 values between 15.31 and 23.51 mM [ 165 ].…”

Section: Syntheses Of Substituted 2-isoxazolines Via 13-dp Cycloaddit...mentioning

confidence: 99%

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

et al. 2023

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The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH2CH=CH2 (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed.

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“…[12] Additionally, their powerful biological activity was reportedforthiazolidin-4-ones and their derivatives, consisting of known heterocyclic nuclei, which play an interesting pharmacological role in anti-HIV, [13][14] antimalarial, [15][16] antibacterial, [17] anticorrosion, [18][19] antioxidant, [20][21] anti-diabetic, [22] antiinflammatory [23] and are active in the design of anticancer agents. [24][25][26][27][28] Furthermore, some of the thiazolidin-4-ones were found to be highly effective against Toxoplasma gondii activity replication [29] and Trypanosomacruzi. [30] In general, they are known for medicinal purposes.…”

Section: Introductionmentioning

confidence: 99%

“…Among these compounds, substituted thiazolidin‐4‐ones mediated significant antiproliferative effects, studies concerning structure‐activity relationships have shown that the cytotoxic potency of compounds was highly dependent on the types and patterns of N‐substitution on the thiazolidin‐4‐one ring [12] . Additionally, their powerful biological activity was reportedforthiazolidin‐4‐ones and their derivatives, consisting of known heterocyclic nuclei, which play an interesting pharmacological role in anti‐HIV, [13–14] antimalarial, [15–16] antibacterial, [17] anticorrosion, [18–19] antioxidant, [20–21] anti‐diabetic, [22] anti‐inflammatory [23] and are active in the design of anticancer agents [24–28] . Furthermore, some of the thiazolidin‐4‐ones were found to be highly effective against Toxoplasma gondii activity replication [29] and Trypanosomacruzi [30] .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Biological and Computational Assessment of New Thiazolidin‐4‐one Derivatives as Potential Anticancer Agents Through the Apoptosis Pathway

et al. 2022

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A variety of novel thiazolidin‐4‐one himachalene derivatives were designed and synthesized through hetero‐cyclization of thiosemicarbazone analogs that have previously exhibited strong anticancer activity. The synthesized products 2 a–4 f were completely characterized by 1H NMR, 13C NMR, IR, and HRMS and were later submitted for in vitro evaluation of their anticancer activity and cytotoxicity on a panel of four human cancer cell lines ( i.eHT‐1080, MCF‐7, A‐549, and MDA‐MB‐231). Most of the evaluated compounds showed potent antiproliferative activities against the four human cancer cell lines with tested IC50 values ranging from 5.25±0.32 to 9.26±0.73 μM. The mechanism of action revealed that compounds 2 b and 4 b induced caspase‐3/7‐activated apoptosis and cell cycle arrest in the G0/G1 stage in HT‐1080 and A‐549 cells. Furthermore, molecular docking studies were conducted to evaluate the binding affinities and the possible binding modes of the top‐performing compounds 2 b and 4 b. This was later supported by Absorption, Distribution, Metabolism, Excretion, and Toxicity (ADMET) analysis predicting their prospective pharmacological profiles. The outcome of this study supports the validity of our strategy and presents 2 b and 4 b as a pattern for the discovery of novel cancer therapeutics.

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Chemical profiling, cytotoxic activities through apoptosis induction in human fibrosarcoma and carcinoma cells, and molecular docking of some 1,2,3-triazole-isoxazoline hybrids using the eugenol as a precursors

Cited by 15 publications

References 57 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

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

Design, Synthesis, Biological and Computational Assessment of New Thiazolidin‐4‐one Derivatives as Potential Anticancer Agents Through the Apoptosis Pathway

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