Convenient Synthesis of Heterocyclic Azo Dyes in the Class of Pyranopyrazoles and Chromenes

Arbabi, Hamidreza; Soltani, Siavash Salek; Salehi, Hasan; Rezazadeh, Shahla; Zonouzi, Afsaneh; Toosibashi, Mansoureh

doi:10.3184/174751918x15177611816526

Cited by 6 publications

(3 citation statements)

References 23 publications

(21 reference statements)

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“…6-Aminopyrimidinone derivative I and the aldehyde derivatives IIa – i were prepared adopting the reported methods. 45 , 50 , 51 …”

Section: Methodsmentioning

confidence: 99%

Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

Abdelgawad¹,

Al‐Sanea²,

Musa³

et al. 2022

JIR

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Background and Purpose Because of gastrointestinal irritation and kidney toxicity associated with non-steroidal anti-inflammatory drugs and the cardiovascular problems of Coxibs use, developing novel anti-inflammatory agents with reduced toxicity and improved selectivity remains a major challenge. Depending on our previous work, a novel series of pyridopyrimidinones IIIa-i has been synthesized via reaction of 6-amino-2-thioxo-2,3-dihydro-1 H -pyrimidin-4-one ( I ) and phenyldiazenyl aromatic aldehydes ( IIa-i ). All the new constructed compounds were fully characterized by elemental and spectral analysis. Methods The target compounds IIIa–i were investigated for their potential towards COX inhibition, anti-inflammatory properties using carrageenan induced edema model in rat paw, and the ulcer indices of the most active members. Results The ethyl pyridopyrmidinone-benzoates IIIf, IIIg and IIIh showed superior inhibitory activity of carrageenan induced edema to celecoxib. Furthermore, the pyridopyrimidinones IIId, IIIf, IIIg , and IIIi exerted improved COX-2 inhibitory activity (IC 50 = 0.67–1.02 µM) comparing to celecoxib (IC 50 = 1.11 µM). Moreover, the gastric ulcerogenic potential assay of compounds IIIf – h revealed their lower ulcerogenic liability than indomethacin with comparable effect to celecoxib. Conclusion Virtual docking investigation of the most active candidates IIId, IIIf, IIIg and IIIi in the active site of COX-2 enzyme showed that these compounds implied interaction and binding motif similar to the cocrystallized ligand bromocelecoxib.

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“…6-Aminopyrimidinone derivative I and the aldehyde derivatives IIa – i were prepared adopting the reported methods. 45 , 50 , 51 …”

Section: Methodsmentioning

confidence: 99%

Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

Abdelgawad¹,

Al‐Sanea²,

Musa³

et al. 2022

JIR

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“…Other catalysts such as Zn(ANA) 2 Cl 2 , [134] Fe 3 -xTixO 4 @SO 3 H nanoparticles, [135] triethylamine (TEA), [136] Fe 3 O 4 @GOQDÀ O-(propane-1-sulfonic acid), [118] SCMNPs@PC/VB1-Zn, [137] SnS-NPs@AC, [138] NaF, NaI, KI, KF, AlCl 3 , FeCl 3 , CuCl 2 , CuI have also been reported for the preparation of pyranopyrazoles, [139] Beside typical pyranopyrazole derivatives, azo-fused pyranopyrazole (10) has been synthesized by the formation of arylidene malononitrile from the 5-(phenyldiazenyl)salicylaldehyde derivative with malononitrile, which further reacted with pyrazolone to yield 62-78 % product. [140] Another azo-substituted pyranopyrazole derivative (11) has also been reported from hydrazine hydrate, malononitrile, ethyl acetoacetate and multifarious aryl azosalicylaldehydes condensation via one-pot strategy under catalyst-free and ultrasound irradiation approach with 82-93 % yield. Among all the synthesized compounds (11), p-nitro compound showed excellent antimicrobial activities with the 0.19 μg/mL MIC value against B. cereus, while unsubstituted and m-chloro compounds showed momentous antifungal activities.…”

Section: Synthesis Of Pyranopyrazoles Via Acetoacetanilide and Pyrazo...mentioning

confidence: 99%

“…Beside typical pyranopyrazole derivatives, azo‐fused pyranopyrazole ( 10 ) has been synthesized by the formation of arylidene malononitrile from the 5‐(phenyldiazenyl)salicylaldehyde derivative with malononitrile, which further reacted with pyrazolone to yield 62–78 % product [140] . Another azo‐substituted pyranopyrazole derivative ( 11 ) has also been reported from hydrazine hydrate, malononitrile, ethyl acetoacetate and multifarious aryl azosalicylaldehydes condensation via one‐pot strategy under catalyst‐free and ultrasound irradiation approach with 82–93 % yield.…”

Section: Introductionmentioning

confidence: 99%

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Farooq,

Ngaini

2024

ChemistrySelect

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Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives. Pyranopyrazole is an important structural unit in heterocyclic chemistry and is useful in pharmaceutical and agrochemical industries. The pyranopyrazole‐based compounds are known in the agricultural industry as herbicides, fungicides, and insecticide agents and in medicinal fields as antimicrobial, anticancer, and antiHIV agents. Despite its wide range of applications, the synthesis of pyranopyrazole has several limitations such as the cost of reagents, potential environmental risks, harsh reaction conditions, longer reaction times, laborious workup procedures, and unsatisfactory yields. However, many studies have been recently reported on the synthesis of pyranopyrazoles using mild, green, and environmentally friendly methods that also give higher yields. Different catalysts and conditions have been reported for the synthesis of pyranopyrazole using four, three, and two components. Among these, four‐component synthesis is commonly reported by using benzaldehyde, hydrazine derivatives, ethyl acetoacetate and malononitrile due to the commercial availability and stability of the reagents. This review summarized the recent synthesis of pyranopyrazole i. e., mono‐ and bis‐pyranopyrazole derivatives via four‐, three‐ and two‐component‐based reactions. Mono‐ and bis‐pyranopyrazole derivatives varied due to the number of pyranopyrazole units that contributed to play an important role in increasing the binding interaction and biological activities beneficial for pharmaceutical industries.

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Synthesis of 6-(aryldiazenyl)-4H-chromene derivatives (microreview)

Доценко

Varzieva

2022

Chem Heterocycl Comp

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Convenient Synthesis of Heterocyclic Azo Dyes in the Class of Pyranopyrazoles and Chromenes

Abstract: A series of novel azo group fused 2 H-chromenes and 4 H-chromenes were synthesised as well as pyranopyrazole derivatives via the Knoevenagel condensation reaction of C–H acid compounds with 5-(arylazo)salicylaldehydes by a nucleophilic addition to the carbonyl group followed cyclisation.

Cited by 6 publications

References 23 publications

Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

Docking Study, Synthesis, and Anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Synthesis of 6-(aryldiazenyl)-4H-chromene derivatives (microreview)

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