Synthesis, <i>in vitro</i> COX-1/COX-2 inhibition testing and molecular docking study of novel 1,4-benzoxazine derivatives

Shaikh, Mohammedumar M.; Patel, Anuj P.; Patel, Shivani; Chikhalia, Kishor H.

doi:10.1039/c9nj00684b

Cited by 13 publications

(5 citation statements)

References 61 publications

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“…Shaikh et al 216 synthesized novel 1,4-benzoxazine derivatives and screened them for anti-inflammatory activity. Optimal COX-II inhibition with IC 50 values of 0.57–0.72 μM was observed from all the compounds with a selectivity index ( S.I. )…”

Section: Recently Reported Cox Inhibitorsmentioning

confidence: 99%

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

et al. 2023

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Innate inflammation beyond a threshold is a significant problem involved in cardiovascular diseases, cancer, and many other chronic conditions. Cyclooxygenase (COX) enzymes are key inflammatory markers as they catalyze prostaglandins production and are crucial for inflammation processes. While COX-I is constitutively expressed and is generally involved in "housekeeping" roles, the expression of the COX-II isoform is induced by the stimulation of different inflammatory cytokines and also promotes the further generation of pro-inflammatory cytokines and chemokines, which affect the prognosis of various diseases. Hence, COX-II is considered an important therapeutic target for drug development against inflammation-related illnesses. Several selective COX-II inhibitors with safe gastric safety profiles features that do not cause gastrointestinal complications associated with classic antiinflammatory drugs have been developed. Nevertheless, there is mounting evidence of cardiovascular side effects from COX-II inhibitors that resulted in the withdrawal of market-approved anti-COX-II drugs. This necessitates the development of COX-II inhibitors that not only exhibit inhibit potency but also are free of side effects. Probing the scaffold diversity of known inhibitors is vital to achieving this goal. A systematic review and discussion on the scaffold diversity of COX inhibitors are still limited. To address this gap, herein we present an overview of chemical structures and inhibitory activity of different scaffolds of known COX-II inhibitors. The insights from this article could be helpful in seeding the development of next-generation COX-II inhibitors.

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Section: Recently Reported Cox Inhibitorsmentioning

confidence: 99%

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

et al. 2023

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“…Most of the FDA-approved non-steroidal anti-inflammatory drugs (NSAIDs), whether they are Salicylates [2], Anthranilic acid [3], Arylindoic acid [4], and Oxicame [5] (Scheme 1), possess common structural features of an acidic or amine of an aromatic or heterocyclic ring, and an additional center of lipophilicity mostly aromatic. Their mechanisms are nonselective, inhibiting both COX-I and COX-II isoforms [6,7]. Density-functional theory (DFT) is a computational quantum mechanical method widely used in modern medicinal chemistry to suggest the electronic 3D atoms or molecule structures compute the ground state energy in realistic models of bulky molecules and their surfaces [8,9].…”

Section: Introductionmentioning

confidence: 99%

“…Docking of Anthranilic acid derivatives (compounds[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] …”

mentioning

confidence: 99%

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2023

J. Med. Chem. Sci.

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Nonsteroidal anti-inflammatories (NSAIDs), are very effective agents in relieving mild to moderate pain and inflammation by inhibiting two isoforms of prostaglandin G-H synthetase (I and II). In the present work, anthranilic acid derivatives' electronic and physicochemical properties are reported utilizing quantum chemical calculations that use the density functional theory (DFT), which forecast physicochemical properties. To clarify the type of chemical composition, drug-likeness, and cyclooxygenase inhibitor, ADME and molecular docking were used. The molecule was highly electrophilic and relatively stable from a quantum chemical computation perspective. The contour maps of HOMO-LUMO and molecule electrostatic potential were examined to display the charge density distributions that might be related to the biological activity.

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“…7 Among them, the intramolecular aminooxygenation of alkynes has evolved as a thriving area of research for the synthesis of various important heterocyclic scaffolds. 8 These studies have involved three strategies (Scheme 2a): (1) oxidation activation of alkynes; (2) alkyne insertion; and (3) radical addition using nitrogen- or oxygen-centered radicals. Generally, intramolecular aminooxygenation reactions of alkynes have been carried out using transition metal catalysts such as rhodium, 9 gold, 10 silver, 11 and copper.…”

Section: Introductionmentioning

confidence: 99%

Electrochemically-initiated intramolecular 1,2-amino oxygenation of alkynes: facile access to formyl- and acyl-substituted indolizines

Yang

et al. 2022

Org. Chem. Front.

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Synthesis, in vitro COX-1/COX-2 inhibition testing and molecular docking study of novel 1,4-benzoxazine derivatives

Abstract: The present work deals with an efficient and straightforward synthesis, biological activity and molecular docking study of novel 1,4-benzoxazine derivatives.

Cited by 13 publications

References 61 publications

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

Design and Development of COX-II Inhibitors: Current Scenario and Future Perspective

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Electrochemically-initiated intramolecular 1,2-amino oxygenation of alkynes: facile access to formyl- and acyl-substituted indolizines

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