Synthesis and antimicrobial activity of novel pyrazolo[3,4-d]pyrimidin derivatives

Khobragade, Chandrahasya N.; Bodade, Ragini G.; Konda, Shankaraiah G.; Dawane, Bhaskar S.; Manwar, Anand V.

doi:10.1016/j.ejmech.2009.12.040

Cited by 41 publications

(20 citation statements)

References 4 publications

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“…Y-700 (10) [19] N-aryl-5-amino-4-cyanopyrazole (11) [20], flavonoids (12) [21], anacardic acid (13) [22] and curcumin (14) [23] also reported to be potent xanthine oxidase inhibitor. Our consistent work on heterocycles [24][25][26] having potent biological activities, prompted us to prepare new thiazolopyrazolyl derivatives bearing different functional moieties and expected to possess potent XO inhibitory activity comparable to Allopurinol along with antioxidant effect.…”

Section: Introductionmentioning

confidence: 99%

Novel thiazolo-pyrazolyl derivatives as xanthine oxidase inhibitors and free radical scavengers

Beedkar

Khobragade

Chobe

et al. 2012

International Journal of Biological Macromolecules

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Section: Introductionmentioning

confidence: 99%

Novel thiazolo-pyrazolyl derivatives as xanthine oxidase inhibitors and free radical scavengers

Beedkar

Khobragade

Chobe

et al. 2012

International Journal of Biological Macromolecules

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“…Due to the biologically importance of the pyrazolo[3,4-d]pyrimidine skeleton especially as antimicrobial agents (Burch 1968;Eweas et al 2012;Khobragade et al 2010), we focused on the synthesis of some novel 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines as potential prodrugs (Vignaroli et al 2013) using ethanolic sodium ethoxide solution. In vitro inhibitory effects of the synthesized compounds against seven gram-positive and -negative bacterial strains were evaluated via measuring inhibition zone diameter (IZD), and determining minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

et al. 2017

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Pyrazolo[3,pyrimidines are one of the most important classes of fused heterocyclic compounds which exhibit a broad range of biological and medicinal properties. They are known as anticancer, antifungal, antibacterial, antiviral and anti-inflammatory agents. In this study, some new 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidine derivatives were prepared via reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile with various nitriles in the presence of sodium ethoxide as catalyst. The inhibitory properties of synthesized compounds were studied according to CLSI guidelines against some pathogenic bacteria including four gram-positive strains (Streptococcus pyogenes, Staphylococcus aureus, Bacillus cereus and Bacillus subtilis subsp. spizizenii) and three gramnegative strains (Pseudomonas aeruginosa, Shigella flexneri and Salmonella enterica subsp. enterica). The antibacterial effects of all derivatives were compared with those of antibiotics belonging to different classes. The values were reported as inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The effect of substituents on the biological activity of derivatives was discussed as well. The inhibitory effect of compound 6a, was shown to be the most, with MIC values in the range of 32-4096 lg/mL. Since most of the synthesized compounds were effective against Streptococcus pyogenes and Pseudomonas aeruginosa, they can be considered as inhibitors of these two bacteria.

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“…Especially, pyrazolopyrimidine derivatives have considerable chemical and pharmacological importance due to their structural similarities with purine. Many of these derivatives were reported to possess various biological effects including antiviral, antimicrobial, anti‐inflammatory, BRAF V600E and VEGFR‐2 dual inhibitors, purine derivative PU3 (II) ( Figure ) and xanthine oxidase inhibitor activities. In addition, pyrazoloquinazoline derivatives have been used as topoisomerase I inhibitors (III) ( Figure ) , potent phosphodiesterase 10 A and Eg5 ATPase, Gly/NMDA receptor and excitatory amino acid antagonists, and potential vaccine virus inhibitors .…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Novel Pyrimidine/Hexahydroquinazoline‐Fused Pyrazolo[3,4‐b]Pyridine Derivatives, Their Biological Evaluation and Docking Studies^#

et al. 2019

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Multicomponent reaction protocol has been developed for the synthesis of novel pyrimidine fused pyrazolo [3,4-b]pyridine derivatives (7 a-g) and hexahydroquinazoline fused pyrazolo [3,4-b] pyridine derivatives (8 a-i) starting from 3-amino-5carbethoxy-6-trifluoromethyl pyrazolo[3,4-b] pyridine 5. All the synthesized compounds were evaluated for antibacterial as well as antifungal activities and compounds 7 f, 8 a, 8 c and 8 d exhibited promising antibacterial activity. In particular, compound 2,4,6-trifluoro substituted pyrimidine fused pyrazolo [3,4-b]pyridine (7 f) showed very good antibacterial activity against the panel of both Gram-positive and -negative bacterial strains. Hexahydroquinazoline fused pyrazolo [3,4-b]pyridine derivatives (8 f-i) also showed promising antifungal activity and broadspectrum anti-biofilm activity against both Gram-positive and negative bacterial strains. The crystal structure of compound 8 b was solved based on single crystal X-ray diffraction study. Docking studies were performed to identify the interactions of the compounds 7 f with crtM enzyme of Staphylococcus aureus.

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Synthesis and antimicrobial activity of novel pyrazolo[3,4-d]pyrimidin derivatives

Cited by 41 publications

References 4 publications

Novel thiazolo-pyrazolyl derivatives as xanthine oxidase inhibitors and free radical scavengers

Novel thiazolo-pyrazolyl derivatives as xanthine oxidase inhibitors and free radical scavengers

Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

Design and Synthesis of Novel Pyrimidine/Hexahydroquinazoline‐Fused Pyrazolo[3,4‐b]Pyridine Derivatives, Their Biological Evaluation and Docking Studies^#

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Synthesis and antimicrobial activity of novel pyrazolo[3,4-d]pyrimidin derivatives

Cited by 41 publications

References 4 publications

Novel thiazolo-pyrazolyl derivatives as xanthine oxidase inhibitors and free radical scavengers

Novel thiazolo-pyrazolyl derivatives as xanthine oxidase inhibitors and free radical scavengers

Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

Design and Synthesis of Novel Pyrimidine/Hexahydroquinazoline‐Fused Pyrazolo[3,4‐b]Pyridine Derivatives, Their Biological Evaluation and Docking Studies#

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Design and Synthesis of Novel Pyrimidine/Hexahydroquinazoline‐Fused Pyrazolo[3,4‐b]Pyridine Derivatives, Their Biological Evaluation and Docking Studies^#