Synthesis, Characterization and Biological Evaluation of Some 2-Arylbenzoxazole Acetic Acid Derivatives as Promising Anticancer Agents

Abualassal, Qais; Jilani, Jamal; Assaf, Areej M.; shmies, Reham Abu

doi:10.32383/appdr/127998

Cited by 3 publications

(2 citation statements)

References 11 publications

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“…The synthetic route started with the synthesis of 4-azido-benzenesulfonamide derivatives 3 and 4 through the reaction of N-butylsulfanilamide 1 or N-cyclohexylsulfanilamide 2 55 with sodium azide. The IR spectrum of 4-azido derivatives 3 and 4 includes the disappearance of the absorption band for NH 2 and the appearance of new bands (2101 and 2100) cm − 1 due to the formation of azide group respectively.…”

Section: Chemistrymentioning

confidence: 99%

Design of Sulfonamide-Based Glycosides Incorporated with 1,2,3-Triazole Scaffold as Potential VEGFR-2 and Carbonic Anhydrase Inhibitors: Synthesis, Cytotoxic Activity and In Silico Studies

El-Bayaa,

Nossier,

El-Manawaty

et al. 2024

Preprint

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The current study reports new sulfonamide-triazole-glycoside hybrids' design, synthesis, and anticancer activity. The target glycosides' cytotoxic activity was studied with a panel of human cancer cell lines. Azido sulfonamide compound 4 exhibited moderate activity against A-549 and HCT-116 and excellent potency against HepG-2 and MCF-7. Replacement of the azido group with 1,2,3-triazole- glycoside hybrids in 6-13 afforded variable activities against tested cell lines ranging from weak to excellent ones in acetylated glycosides 6-9. On the other hand, hydroxylated glycosides 10-13, revealed weak cytotoxicity except N-cyclohexylbenzene derivatives 11, 13 expressing promising activity against HepG-2. In addition, the hydroxylated glycoside 13 gave moderate activity against MCF-7. To detect the probable action mechanism, the inhibitory activity of the promising sulfonamide-triazole-glycoside hybrids was studied against VEGFR-2, carbonic anhydrase isoforms hCA IX and hCA XII. Moreover, the docking evaluation was simulated to supply better rationalization and gain insight into the binding affinity between their targeted enzymes and the promising derivatives and used for further modification in the anticancer field.

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Section: Chemistrymentioning

confidence: 99%

Design of Sulfonamide-Based Glycosides Incorporated with 1,2,3-Triazole Scaffold as Potential VEGFR-2 and Carbonic Anhydrase Inhibitors: Synthesis, Cytotoxic Activity and In Silico Studies

El-Bayaa,

Nossier,

El-Manawaty

et al. 2024

Preprint

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“…Jilani and co-workers 54 synthesized 2-substituted benzoxazole acetic acid derivatives ( 3 ) via an oxidative coupling reaction between methyl-3-amino-4-hydroxyphenylacetate ( 1 ) and aldehydes ( 2 ), catalyzed by lead tetraacetate in ethanol and the further addition of 90% NaOH solution in ethanol and water at RT for 3 h. Their cytotoxic activity against cancer cell lines, namely MCF-7 (human breast cancer cells) and HCT-116 (human colorectal carcinoma cells), was also evaluated. Cytotoxic activity was elevated in the presence of an acetic acid group at the fifth position on the benzoxazole moiety (Scheme 4; method 4).…”

Section: Synthesis Of Benzoxazole Derivativesmentioning

confidence: 99%

Advances in the synthetic strategies of benzoxazoles using 2-aminophenol as a precursor: an up-to-date review

Soni¹,

Sahiba²,

Teli³

et al. 2023

RSC Adv.

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Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use

et al. 2022

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2-(4-Chlorophenyl)-5-benzoxazoleacetic acid (CBA) and its ester, methyl-2-(4-chloro-phenyl)-5-benzoxazoleacetate (MCBA), were synthesized, and their structures were confirmed by 1HNMR, IR, and mass spectrophotometry. The anti-psoriatic activities of CBA and MCBA were tested using an imiquimod (IMQ)-induced psoriatic mouse model, in which mice were treated both topically (1% w/w) and orally (125 mg/kg) for 14 days. The erythema intensity, thickness, and desquamation of psoriasis were scored by calculating the psoriasis area severity index (PASI). The study also included the determination of histopathological alterations in the skin tissues of treated mice. Topical and oral administration of CBA and MCBA led to a reduction in erythema intensity, thickness, and desquamation, which was demonstrated by a significant decrease in the PASI value. In addition, skin tissues of mice treated with CBA and MCBA showed less evidence of psoriatic alterations, such as hyperkeratosis, parakeratosis, scale crust, edema, psoriasiform, and hyperplasia. After administration of either topical or oral dosing, the anti-psoriatic effects were found to be stronger in MCBA-treated than in CBA-treated mice. These effects were comparable to those produced by Clobetasol propionate, the reference drug. This drug discovery could be translated into a potential new drug for future clinical use in psoriasis treatment.

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Synthesis, Characterization and Biological Evaluation of Some 2-Arylbenzoxazole Acetic Acid Derivatives as Promising Anticancer Agents

Cited by 3 publications

References 11 publications

Design of Sulfonamide-Based Glycosides Incorporated with 1,2,3-Triazole Scaffold as Potential VEGFR-2 and Carbonic Anhydrase Inhibitors: Synthesis, Cytotoxic Activity and In Silico Studies

Design of Sulfonamide-Based Glycosides Incorporated with 1,2,3-Triazole Scaffold as Potential VEGFR-2 and Carbonic Anhydrase Inhibitors: Synthesis, Cytotoxic Activity and In Silico Studies

Advances in the synthetic strategies of benzoxazoles using 2-aminophenol as a precursor: an up-to-date review

Synthesis and In-Vivo Evaluation of Benzoxazole Derivatives as Promising Anti-Psoriatic Drugs for Clinical Use

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