Synthesis, tautomerism, and antimicrobial, anti-HCV, anti-SSPE, antioxidant, and antitumor activities of arylazobenzosuberones

Farghaly, Thoraya A.; Abdalla, Mohamed M.

doi:10.1016/j.bmc.2009.10.012

Cited by 52 publications

(27 citation statements)

References 34 publications

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“…Azo compounds have also been shown to be effective antibacterial (Farghaly and Abdalla, 2009) and antitumor (ElShafei et al, 2009) agents. Azo drugs for the treatment of IBD consist of a carrier compound linked via an azo bond to 5-amino salycilic acid (5-ASA).…”

Section: Introductionmentioning

confidence: 99%

Reaction mechanism of azoreductases suggests convergent evolution with quinone oxidoreductases

et al. 2010

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Azoreductases are involved in the bioremediation by bacteria of azo dyes found in waste water. In the gut flora, they activate azo pro-drugs, which are used for treatment of inflammatory bowel disease, releasing the active component 5-aminosalycilic acid. The bacterium P. aeruginosa has three azoreductase genes, paAzoR1, paAzoR2 and paAzoR3, which as recombinant enzymes have been shown to have different substrate specificities. The mechanism of azoreduction relies upon tautomerisation of the substrate to the hydrazone form. We report here the characterization of the P. aeruginosa azoreductase enzymes, including determining their thermostability, cofactor preference and kinetic constants against a range of their favoured substrates. The expression levels of these enzymes during growth of P. aeruginosa are altered by the presence of azo substrates. It is shown that enzymes that were originally described as azoreductases, are likely to act as NADH quinone oxidoreductases. The low sequence identities observed among NAD(P)H quinone oxidoreductase and azoreductase enzymes suggests convergent evolution.

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Section: Introductionmentioning

confidence: 99%

Reaction mechanism of azoreductases suggests convergent evolution with quinone oxidoreductases

et al. 2010

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“…The pentacyclic system 112 was also formed by azo coupling of compound 1 (R = R 1 = H) with the enaminone 113 under standard conditions [185]. Analogous Yapp-Klingemann reaction was possible by using benzosuberone derivative 114 [186]. The interaction of pyrazole-3(5)-diazonium salts 1 with 1,3-indanedione has been described, resulting in the formation of a tetracyclic system, indeno[1,2-e]pyrazolo[5,1-c]-1,2,4-triazin-6-one 117 [129,187,188].…”

Section: Intermolecular Azo Couplingmentioning

confidence: 99%

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Ledenyova

Didenko

Shikhaliev

2014

Chem Heterocycl Comp

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The methods of synthesis, structure, reactivity, and synthetic utility of pyrazole-3(5)-diazonium salts are reviewed here for the first time, with emphasis on heterocyclization reactions of these compounds.More than one hundred years have passed since α-diazo derivatives of pyrazole were discovered. A substantial amount of knowledge has been accumulated over this time regarding the stability, structure, and transformations of these compounds. However, the chemistry of pyrazole-3(5)-diazonium salts developed rapidly only in the second half of the 20th century, with many studies performed in various countries, in particular Germany, Egypt, Russia, and Japan. Unfortunately, no systematic review has been compiled for the wide range of data about pyrazole-3(5)-diazonium salts. Some aspects regarding the properties of these compounds have been discussed in reviews and monographs on other topics [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].

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“…1). From the above findings and in continuation of our research projects in the utility of enaminones in the synthesis of new polyaza-heterocyclic ring systems [10][11][12][13][14], we interested in this report to synthesize a new tri-enaminone, which is unreported hitherto, and used it as precursor for synthesis of some polyaza-heterocycles. Literature reports indicated that polyaza-heterocycles, like poly-pyrazoles, poly-pyridines, and poly-pyrimidines, were found to be useful in various pharmaceutical, agrochemicals, photographic, and other applications.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of a Novel Tri‐enaminone as Building Block for Polyaza‐heterocycles

Farghaly

Abdallah

Aziz

2016

Journal of Heterocyclic Chem

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The new tri‐enaminone, namely, 3,4‐bis(3‐dimethylamino‐2‐propenoyl)‐1‐[4‐(3‐dimethylamino‐2‐propenoyl)phenyl]‐5‐methyl‐1H‐pyrazole was prepared and used as building block for synthesis of novel polyaza‐heterocycles. The latter compounds were obtained via an efficient one‐pot reaction of the tri‐enaminone with 1,3‐dipoles and various electrophilic and nucleophilic reagents. The structures of the new products were confirmed based on elemental and spectral analyses. Also, alternative synthetic methods were carried out wherever possible as further evidence for some of the newly synthesized products.

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Synthesis, tautomerism, and antimicrobial, anti-HCV, anti-SSPE, antioxidant, and antitumor activities of arylazobenzosuberones

Cited by 52 publications

References 34 publications

Reaction mechanism of azoreductases suggests convergent evolution with quinone oxidoreductases

Reaction mechanism of azoreductases suggests convergent evolution with quinone oxidoreductases

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Synthesis of a Novel Tri‐enaminone as Building Block for Polyaza‐heterocycles

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