Ecofriendly synthesis of pyrano[2,3‐<i>d</i>]pyrimidine derivatives and related heterocycles with anti‐inflammatory activities

Abdelazim, Mohamed H.; Aziz, Maged A.; Mouneir, Samar M.; El‐Farargy, Ahmed F.; Shehab, Wesam S.

doi:10.1002/ardp.202000084

Cited by 32 publications

(23 citation statements)

References 34 publications

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“…Finally, the reaction of malononitrile with the start chalcone yielded 2-amino-6-(1 H -indol-3-yl)-4-(thiophen-2-yl)-4 H -pyran-3-carbonitrile ( 11 ) with a poly-functional pyrane ring, which can pave the way to synthesize a new series of novel compounds ( 12a – e ) Scheme 5 . A vicinal amino and cyano group can generate a wide range of various heterocyclic compounds [ 10 , 11 ]. In this regard, we envisioned synthesizing imine products by reacting the amino group of 11 with various aldehydes via different condensation reactions.…”

Section: Resultsmentioning

confidence: 99%

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Design, Synthesis, Biological Evaluation, 2D-QSAR Modeling, and Molecular Docking Studies of Novel 1H-3-Indolyl Derivatives as Significant Antioxidants

Aziz

Shehab

Al‐Karmalawy

et al. 2021

IJMS

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Novel candidates of 3-(4-(thiophen-2-yl)-pyridin/pyran/pyrimidin/pyrazol-2-yl)-1H-indole derivatives (2–12) were designed by pairing the pyridine/pyrane/pyrimidine/pyrazole heterocycles with indole and thiophene to investigate their potential activities as (2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) inhibitors. The purpose of these derivatives’ modification is to create high-efficiency antioxidants, especially against ABTS, as a result of the efficiency of this set of key heterocycles in the inhibition of ROS. Herein, 2D QSAR modeling was performed to recommend the most promising members for further in vitro investigations. Furthermore, the pharmacological assay for antioxidant activity evaluation of the yielded indole-based heterocycles was tested against ABTS (2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid); by utilizing ascorbic acid as the standard. Candidate 10 showed higher antioxidant activity (IC50 = 28.23 μg/mL) than ascorbic acid itself which achieved (IC50 = 30.03 μg/mL). Moreover, molecular docking studies were performed for the newly designed and synthesized drug candidates to propose their mechanism of action as promising cytochrome c peroxidase inhibitors compared to ascorbic acid as a reference standard. Our findings could be promising in the medicinal chemistry scope for further optimization of the newly designed and synthesized compounds regarding the introduced structure-activity relationship study (SAR) in order to get a superior antioxidant lead compound in the near future.

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Section: Resultsmentioning

confidence: 99%

“…Admittedly, heterocyclic moieties have vital biological activities, particularly that containing nitrogen, oxygen, and sulfur atoms [ 10 , 11 ]. Based on our belief in the importance of these candidates, in this paper, we prepared new series containing the indole nucleus and tested their effectiveness as antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Biological Evaluation, 2D-QSAR Modeling, and Molecular Docking Studies of Novel 1H-3-Indolyl Derivatives as Significant Antioxidants

Aziz

Shehab

Al‐Karmalawy

et al. 2021

IJMS

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“…The IC 50 values of the two compounds (5 and 6) against COX-2 inhibition were reported to be 0.04 AE 0.09 mmol and 0.04 AE 0.02 mmol, respectively as compared to the standard drug celecoxib (IC 50 ¼ 0.04 AE 0.01 mmol). 76 Synthesis of several substituted 1H-pyrazolyl-thiazolo[4,5-d] pyrimidine derivatives has been reported. The results of two bioassays namely carrageenan-induced paw edema and cotton pellet-induced granuloma in rats indicated that pyrimidine derivatives (7-9) (Fig.…”

Section: Cyclooxygenase Inhibitionmentioning

confidence: 99%

Research developments in the syntheses, anti-inflammatory activities and structure–activity relationships of pyrimidines

et al. 2021

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“…On the other hand, the pyrimidine ring has unique pharmacological activities [ 12 ]. In this regard, chemists make many and various attempts to discover novel pyrimidine derivatives via different synthetic strategies and utilize various important catalysts [ 13 , 14 , 15 ]. Fused pyrimidines were designed and evaluated as antitumors [ 16 ], antioxidants [ 17 ], and anticancer [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives

et al. 2022

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On our way to discovering and developing compounds that have an antioxidant impact compared to ascorbic acid and other biological activities, we designed, synthesized, and evaluated a new series of heterocyclic moieties drugs (1–11) as antioxidants and antimicrobial agents. As starting moieties, these new candidates were derived from two promising heterocyclic compounds, imidazoldin-4-one and thiazol-4-one. Firstly, diphenylimidazol 1 was obtained because of the cyclo condensation one-pot ternary reaction of urea, aniline, and chloroacetic acid under thermal conditions. Out of this starting compound, we could design and create new vital rings such as purine and triazine as in compounds 5 and 6, respectively. Secondly, the start thiazole derivative 7 was obtained from the intermolecular cyclization of thiourea, chloroacetic acid, p-nitobezaldehyde in the presence of sodium acetate. We synthesized various derivatives from this second starting compound 7 by being subjected to different reagents such as aniline, phenylenediamine, phenylhydrazine, and barbituric acid to yield 8, 9, 10, and 11, respectively. Using ascorbic acid as the standard compound, the pharmacological testing for antioxidant activity assessment of the produced derivatives was evaluated against ABTS (2,20-azinobis (3-ethylbenzothiazoline-6-sulfonic acid). Candidate 6 exhibited the best activity as an antioxidant agent compared to ascorbic acid as a reference compound. Moreover, all compounds were evaluated as antimicrobial agents against a series of bacteria and fungi. Among all synthesized compounds, compound 6 achieved high efficiency against two types of fungi and four kinds of bacteria, as Clotrimazole and Ampicillin were used as the reference agents, respectively. All chemical structures of the novel synthesized candidates were unequivocally elucidated and confirmed utilizing spectroscopical and elemental investigations.

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Ecofriendly synthesis of pyrano[2,3‐d]pyrimidine derivatives and related heterocycles with anti‐inflammatory activities

Cited by 32 publications

References 34 publications

Design, Synthesis, Biological Evaluation, 2D-QSAR Modeling, and Molecular Docking Studies of Novel 1H-3-Indolyl Derivatives as Significant Antioxidants

Design, Synthesis, Biological Evaluation, 2D-QSAR Modeling, and Molecular Docking Studies of Novel 1H-3-Indolyl Derivatives as Significant Antioxidants

Research developments in the syntheses, anti-inflammatory activities and structure–activity relationships of pyrimidines

Design, Synthesis, Molecular Docking, and Evaluation Antioxidant and Antimicrobial Activities for Novel 3-Phenylimidazolidin-4-One and 2-Aminothiazol-4-One Derivatives

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