Review on Chemistry of Oxazole derivatives: Current to Future Therapeutic Prospective

Joshi, Sweta; Mehra, Meenakshi; Singh, Ramandeep; Kakar, Satinder

doi:10.1080/2314808x.2023.2171578

Cited by 8 publications

(4 citation statements)

References 61 publications

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“…When we compared the activity of the arylidene dipterocarpol derivatives the compounds containing oxygen function ( 3 a , 3 c , 3 e , 3 l , 3 m and 3 n ) with native side chains possess better results. It was confirmed that derivatives containing oxygen atoms exhibited improved biological activity [66] . The lead‐compounds were identified as p ‐hydroxy‐benzylidene 3 l and p‐ ald‐benzylidene 3 m and acted as the most active inhibitors of α‐glucosidase with IC 50 0.753±0.074 and 0.204±0.026 μM, being 232‐ and 857‐times more active than inhibitor acarbose.…”

Section: Resultsmentioning

confidence: 87%

“…It was confirmed that derivatives containing oxygen atoms exhibited improved biological activity. [66] The lead-compounds were identified as p-hydroxy-benzylidene 3 l and p-ald-benzylidene 3 m and acted as the most active inhibitors of α-glucosidase with IC 50 0.753 � 0.074 and 0.204 � 0.026 μM, being 232-and 857-times more active than inhibitor acarbose. Among the 3-oxo-dammar-20(24)-diene derivatives, the compounds 4 l and 4 m also showed the best activity with IC 50 11.31 � 2.0 and 8.42 � 1.25 μM.…”

Section: Inhibition Of α-Glucosidasementioning

confidence: 99%

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New Dipterocarpol‐Based Molecules with α‐Glucosidase Inhibitory and Hypoglycemic Activity

Smirnova,

Galimova,

Sapozhnikova

et al. 2023

ChemBioChem

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Dammarane triterpenoids are affordable and bioactive natural metabolites with great structural potential, which makes them attractive sources for drug development. The aim of the study was to investigate the potency of new dipterocarpol derivatives for the treatment of diabetes. Two dammaranes (dipterocarpol and its 20(24)‐diene derivative) were modified by a Claisen‐Schmidt aldol condensation to afford C2(E)‐arylidenes in good yields. The majority of the synthesized compounds exhibited an excellent‐to‐moderate inhibitory effect toward α‐glucosidase (from S. saccharomyces), among them eight compounds showed IC50 values less than 10 μM. 3‐Oxo‐dammarane‐2(E)‐benzylidenes (holding p‐hydroxy‐ 3 l and p‐carbonyl‐ 3 m substituents) demonstrated the most potent α‐glucosidase inhibition with IC50 0.753 and 0.204 μM, being 232‐ and 857‐times more active than acarbose (IC50 174.90 μM), and a high level of NO inhibition in Raw 264.7 cells with IC50 of 1.75 and 4.57 μM, respectively. An in vivo testing of compound 3 m (in a dose of 20 mg/kg) on a model of streptozotocin‐induced T1DM in rats showed a pronounced hypoglycemic activity, the ability to reduce effectively the processes of lipid peroxidation in liver tissue and decrease the excretion of glucose and pyruvic acid in the urine. Compound 3 m reduced the death of diabetic rats and preserved their motor activity.

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Section: Resultsmentioning

confidence: 87%

Section: Inhibition Of α-Glucosidasementioning

confidence: 99%

New Dipterocarpol‐Based Molecules with α‐Glucosidase Inhibitory and Hypoglycemic Activity

Smirnova,

Galimova,

Sapozhnikova

et al. 2023

ChemBioChem

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“…There is no general synthetic approach leading to these structures and each type of product requires a specic methodology. Despite the availability of numerous synthetic methods for the preparation of mono-or di-substituted oxazoles, 7 access to tri-substituted 4-carbonyl oxazoles is not well explored and relies mainly on the intramolecular Cu-catalyzed cyclization of (thio)enamides 8 or bromo(thio) enones, 9 or on a protocol starting from 2-azido enones 10 or alkynyl ketones. 11 2-N-substituted indenones can be accessed from ynamides, 12 2-alkynylbenzoyl cyanides, 13 or 2-hydroxy-substituted internal alkynes.…”

Section: Introductionmentioning

confidence: 99%

Lewis acid-mediated transformations of 5-acyl-N-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles

Janecký,

Beier

2024

RSC Adv.

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“…Oxazole is another vital pharmacophore responsible for a diverse array of pharmacological activity, such as anti-fungal, antibacterial, antimalarial, and anticancer activity [11,12]. Various clinically available molecules, such as linezolid, furazolidone, toloxatone, oxaprozin, ditazole, and aleglitazar contain oxazole as a core scaffold [13].…”

Section: Introductionmentioning

confidence: 99%

Cerric ammonium nitrate catalyzed eco-friendly green synthesis of chitosan Schiff base using PEG-400 as an anticancer agent against gastric cancer cells via inhibiting EGFR

Geng,

Feng,

et al. 2024

Bull. Chem. Soc. Eth.

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The present study was conducted to scrutinize the pharmacological effect of oxazole-embedded Chitosan as an anticancer agent against gastric cancer cells. This compound was synthesized using the classical Schiff base reaction but utilizing the novel green chemical process where cerric ammonium nitrate (CAN) was used as a catalyst in the PEG-400 as solvent media. The target compound was obtained with an excellent yield at the catalyst loading of 5% CAN concentration in 15 min. The Kinase-Glo Plus luminescence kinase assay kit was used to determine the EGFR inhibitory activity of compound 1 where it showed potent activity with IC50 of 2.14 µM. Its effect was also determined on the cellular viability of the Human gastric cancer cell line (SGC7901), liver cancer cell line (HepG2), and lung cancer cell line (A549), where it exhibits potent activity against SGC7901. The compound further showed the concentration-dependent inhibitory effect on migration and invasion of SGC7901. In RT-qPCR analysis, the compound showed induction of apoptosis of SGC7901 cells possibly by restoring the expression of Bcl-2 and Bax near to normal, and inhibition of the mRNA expression of EGFR in a concentration-dependent manner. KEY WORDS: Schiff base, Chitosan, EGFR, mRNA, apoptosis, Bcl-2 Bull. Chem. Soc. Ethiop. 2024, 38(4), 1091-1101. DOI: https://dx.doi.org/10.4314/bcse.v38i4.22

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Review on Chemistry of Oxazole derivatives: Current to Future Therapeutic Prospective

Cited by 8 publications

References 61 publications

New Dipterocarpol‐Based Molecules with α‐Glucosidase Inhibitory and Hypoglycemic Activity

New Dipterocarpol‐Based Molecules with α‐Glucosidase Inhibitory and Hypoglycemic Activity

Lewis acid-mediated transformations of 5-acyl-N-fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles

Cerric ammonium nitrate catalyzed eco-friendly green synthesis of chitosan Schiff base using PEG-400 as an anticancer agent against gastric cancer cells via inhibiting EGFR

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