Design, synthesis of 2,3-disubstitued 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents: COX-1/2 inhibitory activities and molecular docking studies

Abdel‐Aziz, Alaa A.‐M.; Abou-Zeid, Laila A.; Eltahir, K; Mohamed, Menshawy A.; El-Enin, Mohamed A. Abu; El‐Azab, Adel S.

doi:10.1016/j.bmc.2016.06.026

Cited by 78 publications

(31 citation statements)

References 38 publications

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“…Quinazolinone compound F was also used as a selective COX‐2 inhibitor . Furthermore, they act as a ingenious building block for diverse natural products (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

et al. 2018

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A novel water assisted strategy has been developed for the synthesis of quinazolinones by the reaction of o‐aminobenzamides 1 with benzyl alcohols 2 using NaCl in regioselective manner under microwave radiation (MW). NaCl and water plays an unprecedented and vital role in the reaction. NaCl create more space for the reactants in aqueous media and bring them in very close proximity for C−N bond formation through “kosmotropes perturbation”. There is no need of any metal, ligand and base for further activation of the reactants in the reaction because water trigger the reaction via “ambiphilic dual activation” of reactants through hydrogen bond accepter and donor ability in the pertinent C−N bond forming steps in the reaction. This “kosmotropes perturbation” and “ambiphilic dual activation” is the accountable attribute for making a new water‐assisted strategy. Several controlled experiments have been carried out to establish the suitable mechanism and stipulation of the reactions. The process illustrated significant selectivity for quinazolinones over dihydrogenated quinazolinones.

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“…Quinazolinone compound F was also used as a selective COX‐2 inhibitor . Furthermore, they act as a ingenious building block for diverse natural products (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

et al. 2018

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“…In 1894, Niementowski published a synthetic procedure for the preparation of quinazoline derivatives through the reaction of anthranilic acid and ketones . According to the importance of quinazoline and quinazolinone compounds in medicinal chemistry, Niementowski reaction conditions were developed and modified to gain a diverse library of such compounds . According to our previous research in the field of catalysis, and also due to the importance of nanomagnetic catalysts in organic syntheses, herein, we want to introduce the first application of prepared SrFe 12 O 19 MNPs as catalyst in the modified Niementowski reaction.…”

Section: Introductionmentioning

confidence: 99%

The use of SrFe₁₂O₁₉ magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

Ziarani

Asl

Gholamzadeh

et al. 2017

Applied Organom Chemis

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Nanomagnetic SrFe 12 O 19 was synthesized through a simple sol-gel auto-combustion and then characterized by FT-IR, XRD, EDXA, VSM, BET and SEM image. Moreover, it was used as catalyst for the first time in the modified Niementowski reaction to investigate its catalytic activity. According to the high yield of quinazolinone products obtained within short reaction times, it was found that SrFe 12 O 19 can be used as an effective and green nanocatalyst in organic reactions.The nanomagnetic catalyst can be easily separated from the reaction mixture using an external magnet.

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“…Heterocyclic structures play a pivotal role in many pharmaceutical, agrochemical, and veterinary products, like quinazolines. An increasing number of quinazoline derivatives have been reported to possess antibacterial [15], anticancer [16], antitubercular [17], anti-HIV [18], antifungal [19], analgesic [20], anti-inflammatory [21], anticonvulsant [22], antiparkinson [23], anthelmintic [24], anti-histaminic [25], and antihypertensive activities [26]. Much attention has been focused on their structures and bioactivity.…”

Section: Introductionmentioning

confidence: 99%

Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy

Zhu

et al. 2016

Molecules

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Abstract:In the present study, 3-(fluorobenzylideneamino)-6-chloro-1-(3,3-dimethylbutanoyl)-phenyl-2,3-dihydroquinazolin-4(1H)-one (FDQL) derivatives have been designed and synthesized to study the interaction between fluorine substituted dihydroquinazoline derivatives with human serum albumin (HSA) using fluorescence, circular dichroism and Fourier transform infrared spectroscopy. The results indicated that the FDQL could bind to HSA, induce conformation and the secondary structure changes of HSA, and quench the intrinsic fluorescence of HSA through a static quenching mechanism. The thermodynamic parameters, ∆H, ∆S, and ∆G, calculated at different temperatures, revealed that the binding was through spontaneous and hydrophobic forces and thus played major roles in the association. Based on the number of binding sites, it was considered that one molecule of FDQL could bind to a single site of HSA. Site marker competition experiments indicated that the reactive site of HSA to FDQL mainly located in site II (subdomain IIIA). The substitution by fluorine in the benzene ring could increase the interactions between FDQL and HSA to some extent in the proper temperature range through hydrophobic effect, and the substitution at meta-position enhanced the affinity greater than that at para-and ortho-positions.

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Design, synthesis of 2,3-disubstitued 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents: COX-1/2 inhibitory activities and molecular docking studies

Cited by 78 publications

References 38 publications

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

The use of SrFe₁₂O₁₉ magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy

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Design, synthesis of 2,3-disubstitued 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents: COX-1/2 inhibitory activities and molecular docking studies

Cited by 78 publications

References 38 publications

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

Kosmotropes Perturbation and Ambiphilic Dual Activation: Responsible Features for the Construction of C‐N Bond towards the Synthesis of Quinazolin‐4(3H)‐ones in Water

The use of SrFe12O19 magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

Comparative Studies of Interactions between Fluorodihydroquinazolin Derivatives and Human Serum Albumin with Fluorescence Spectroscopy

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The use of SrFe₁₂O₁₉ magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction