Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis

Puttaswamy, Naveen; Kumar, G Santhosh; Al‐Ghorbani, Mohammed; Vigneshwaran, V.; Prabhakar, B.T.; Khanum, Shaukath Ara

doi:10.1016/j.ejmech.2016.02.052

Cited by 22 publications

(8 citation statements)

References 26 publications

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“…Interestingly, among salicylic acid derivatives containing an isoxazole ring, 3-(4-methoxyphenyl)-4-(3-hydroxy-4-carboxybenzoyl)-5-(3-chlorophenyl)-4,5-dihydroisoxazoline ( 8e ), which demonstrated mitogenic activity towards human lymphocytes and mouse splenocytes, was found [ 39 ]. The ability of the compound to stimulate cell division was caused by increased IL-2 secretion.…”

Section: Resultsmentioning

confidence: 99%

Isoxazole Derivatives as Regulators of Immune Functions

2018

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In this review, we present reports on the immunoregulatory properties of isoxazole derivatives classified into several categories, such as immunosuppressive, anti-inflammatory, immunoregulatory, and immunostimulatory compounds. The compounds were tested in various models using resident cells from rodents and humans, cell lines, and experimental animal disease models corresponding to human clinical situations. Beneficial features of the described isoxazole derivatives include low toxicity and good bioactivity at low doses. In a majority of studies, the activities of investigated compounds were comparable or even higher than registered reference drugs. Whenever possible, a plausible mechanism of action of the investigated compounds and their potential therapeutic utility were proposed. Among the described compounds, particular attention was paid to the class of immune stimulators with a potential application in chemotherapy patients.

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Section: Resultsmentioning

confidence: 99%

Isoxazole Derivatives as Regulators of Immune Functions

2018

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“…Several isoxazole-based compounds with various substituents are now being investigated as anticancer drugs. 11 , 12 Previous studies by other research groups have shown that adding a five-membered heterocyclic ring to specific drugs can help enhance CA inhibitory action. 13 − 16 …”

Section: Introductionmentioning

confidence: 99%

“…Isoxazole fragments are also widely used to alter lead compounds for increased efficacy in the realm of anti-tumor drugs. Several isoxazole-based compounds with various substituents are now being investigated as anticancer drugs. , Previous studies by other research groups have shown that adding a five-membered heterocyclic ring to specific drugs can help enhance CA inhibitory action. − …”

Section: Introductionmentioning

confidence: 99%

Isoxazole Derivatives against Carbonic Anhydrase: Synthesis, Molecular Docking, MD Simulations, and Free Energy Calculations Coupled with In Vitro Studies

et al. 2022

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Heterocyclic compounds with a five-membered ring as a core, particularly those containing more than one heteroatom, have a wide spectrum of biological functions, especially in enzyme inhibition. In this study, we present the synthesis of five-membered heterocyclic isoxazole derivatives via sonication of ethyl butyrylacetate with aromatic aldehyde in the presence of a SnII-Mont K10 catalyst. The synthesized compounds were characterized using sophisticated spectroscopic methods. In vitro testing of the compounds reveals three derivatives with significant inhibitory action against carbonic anhydrase (CA) enzyme. The compound AC2 revealed the most promising inhibitory activity against CA among the entire series, with an IC 50 = 112.3 ± 1.6 μM (% inh = 79.5) followed by AC3 with an IC 50 = 228.4 ± 2.3 μM (% inh = 68.7) compared to the standard with 18.6 ± 0.5 μM (% inh = 87.0). Molecular docking (MD) study coupled with extensive MD simulations (400 ns) and MMPBSA study fully supported the in vitro enzyme inhibition results, evident from the computed Δ G bind (AC2 = −13.53 and AC3 = −12.49 kcal/mol). The in vitro and in silico studies are also augmented by a fluorescence-based enzymatic assay in which compounds AC2 and AC3 showed significant fluorescence enhancement. Therefore, on the basis of the present study, it is inferred that AC2 and AC3 may serve as a new framework for designing effective CA inhibitors.

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“…Many reports mentioned that aspirin can reduce the risk of cancer [27] , [28] , [29] , [30] , [31] , [32] , [33] and inhibit NFκβ signal which may assist in cancer growth and metastasis [34] , [35] . This is why many researchers adopted investigation of aspirin based-analogues as potential antitumor candidates [36] , [37] , [38] , [39] . Others considered conjugation of aspirin with antitumor chemotherapeutics [40] because inflammation initiated by cancer may lead to metastasis [41] .…”

Section: Introductionmentioning

confidence: 99%