Synthesis and biological activity of pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4-one derivatives: in silico approach

Khobragade, Chandrahasya N.; Bodade, Ragini G.; Dawane, Bhaskar S.; Konda, Shankaraiah G.; Khandare, Namdev T.

doi:10.3109/14756360903389849

Cited by 23 publications

(9 citation statements)

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“…Development of XO inhibitors with free radical scavengers potential may prove to be promising agents to treat Gout. This encouraged the researchers to develop structurally diverse molecules without purine backbone with promising XO inhibitory activity such as N‐(1,3‐diaryl‐3‐oxopropyl) amides ( 4 ) ,1‐acetyl‐3,5‐diaryl‐4,5‐di‐hydrol(1H) pyrazoles ( 5 ) , Y‐700 ( 6 ) , N‐aryl‐5‐amino‐4‐cyanopyrazole (7) , flavonoids ( 8 ) , anacardic acid ( 9) , thiazolo‐pyrazolyl 5‐phenylisoxazole‐3‐carboxylic acid ( 10 ) , naphthoflavones ( 11 ) , and pyrazolo[3,4‐d] thiazolo[3,2‐a]pyrimidin‐4‐one ( 12 ) , 2‐(3‐cyano‐2‐isopropyl‐1H‐indol‐5‐yl)‐4‐methylthiazole‐5‐carboxylic acid ( 13 ) , derivatives (Figure ). It was assumed worthwhile to rationally design with pharmacophoric approaches to develop structural analogous of febuxostat as non‐purine XO inhibitors with antioxidant activity for diminishing the associated toxicities.…”

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Development of 2‐(Substituted Benzylamino)‐4‐Methyl‐1, 3‐Thiazole‐5‐Carboxylic Acid Derivatives as Xanthine Oxidase Inhibitors and Free Radical Scavengers

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A series of 2-(substituted benzylamino)-4-methylthiazole-5-carboxylic acid was designed and synthesized as structural analogue of febuxostat. A methylene amine spacer was incorporated between the phenyl ring and thiazole ring in contrast to febuxostat in which the phenyl ring was directly linked with the thiazole moiety. The purpose of incorporating methylene amine was to provide a heteroatom which is expected to favour hydrogen bonding within the active site residues of the enzyme xanthine oxidase. The structure of all the compounds was established by the combined use of FT-IR, NMR and MS spectral data. All the compounds were screened in vitro for their ability to inhibit the enzyme xanthine oxidase as per the reported procedure along with DPPH free radical scavenging assay. Compounds 5j, 5k and 5l demonstrated satisfactory potent xanthine oxidase inhibitory activities with IC50 values, 3.6, 8.1 and 9.9 μm, respectively, whereas compounds 5k, 5n and 5p demonstrated moderate antioxidant activities having IC50 15.3, 17.6 and 19.6 μm, respectively, along with xanthine oxidase inhibitory activity. Compound 5k showed moderate xanthine oxidase inhibitory activity as compared with febuxostat along with antioxidant activity. All the compounds were also studied for their binding affinity in active site of enzyme (PDB ID-1N5X).

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Development of 2‐(Substituted Benzylamino)‐4‐Methyl‐1, 3‐Thiazole‐5‐Carboxylic Acid Derivatives as Xanthine Oxidase Inhibitors and Free Radical Scavengers

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“…They have also been reported as calcium antagonists [11], group 2 metabotropic glutamate receptor antagonists [12], 5-HT2 receptor antagonists [13,14], and inhibitors of enzymes such as xanthine oxidase [15], acetylcholinesterase [16], and CDC25B phosphatise [17]. Some of the biologically potent thiazolopyrimidine and thiazoloquinazoline derivatives are given in Fig.…”

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Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction

et al. 2015

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A highly efficient method has been developed for synthesis of 7,9-disubstituted-6,7-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazolines via multicomponent onepot two-step tandem reaction involving 1-tetralone, arylaldehydes, thiourea, and 4-chlorophenacyl bromide/(3-bromoacetyl)coumarin utilizing p-toluenesulfonic acid as catalyst in glacial acetic acid under reflux conditions. Analytically pure products are formed with excellent yield and short reaction time. All the synthesized compounds were confirmed by their spectral and elemental analyses. Graphical abstract Keywords Benzo[h]thiazolo[2,3-b]quinazoline Á Coumarin Á Multicomponent reaction Á Phenacyl bromide Á 1-Tetralone Electronic supplementary material The online version of this article (

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“…Pyrazole derivatives are well known for their applications in fluorescence probes and pharmacological activities such as anti-microbial, antiinflammatory, anti-cancer, and antiviral [20e23]. Recently, pyrazoles were found to possess inhibitory activities against XO, cyclooxygenase, and alkaline phosphatases [24,25]. The modification of pyrazole and oxadiazole such as substituent moiety should provide potential fluorescence properties and biological activities.…”

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confidence: 99%

Synthesis, crystal structures, fluorescence and xanthine oxidase inhibitory activity of pyrazole-based 1,3,4-oxadiazole derivatives

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et al. 2015

Journal of Molecular Structure

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Synthesis and biological activity of pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidin-4-one derivatives: in silico approach

Cited by 23 publications

References 24 publications

Development of 2‐(Substituted Benzylamino)‐4‐Methyl‐1, 3‐Thiazole‐5‐Carboxylic Acid Derivatives as Xanthine Oxidase Inhibitors and Free Radical Scavengers

Development of 2‐(Substituted Benzylamino)‐4‐Methyl‐1, 3‐Thiazole‐5‐Carboxylic Acid Derivatives as Xanthine Oxidase Inhibitors and Free Radical Scavengers

Benzo[h]thiazolo[2,3-b]quinazolines by an efficient p-toluenesulfonic acid-catalyzed one-pot two-step tandem reaction

Synthesis, crystal structures, fluorescence and xanthine oxidase inhibitory activity of pyrazole-based 1,3,4-oxadiazole derivatives

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