Synthesis and biological evaluation of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives

Dhiman, Priyanka; Malik, Neelam; Verma, Prabhakar Kumar; Khatkar, Anurag

doi:10.1007/s11164-015-1922-8

Cited by 12 publications

(6 citation statements)

References 20 publications

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“…The antioxidant potential of rutin derivatives was performed by DPPH method evaluated in the form of IC 50 estimated using the ELISA plate reader EPOCH™ “MICROPLATE READER (BIOTEK). This method opted for evaluation of free radical scavenging activity of DPPH was based on modified procedure described by Dhiman et al [36]. The tested compounds were prepared in methanolic solution and reacted with methanolic solution of DPPH at 37 °C.…”

Section: Methodsmentioning

confidence: 99%

In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors

2019

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Background Xanthine oxidase is an important enzyme of purine catabolism pathway and has been associated directly in pathogenesis of gout and indirectly in many pathological conditions like cancer, diabetes and metabolic syndrome. In this research rutin, a bioactive flavonoid was explored to determine the capability of itself and its derivatives to inhibit xanthine oxidase. Objective To develop new xanthine oxidase inhibitors from natural constituents along with antioxidant potential. Method In this report, we designed and synthesized rutin derivatives hybridized with hydrazines to form hydrazides and natural acids to form ester linkage with the help of molecular docking. The synthesized compounds were evaluated for their antioxidant and xanthine oxidase inhibitory potential. Results The enzyme kinetic studies performed on rutin derivatives showed a potential inhibitory effect on XO ability in competitive manner with IC 50 value ranging from 04.708 to 19.377 µM and RU3a 3 was revealed as most active derivative. Molecular simulation revealed that new rutin derivatives interacted with the amino acid residues PHE798, GLN1194, ARG912, GLN 767, ALA1078 and MET1038 positioned inside the binding site of XO. Results of antioxidant activity revealed that all the derivatives showed very good antioxidant potential. Conclusion Taking advantage of molecular docking, this hybridization of two natural constituent could lead to desirable xanthine oxidase inhibitors with improved activity. Electronic supplementary material The online version of this article (10.1186/s13065-019-0585-8) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors

2019

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“…In addition, our goal was to incorporate one α‐propargyl‐β‐caprolactone unit per chain. The purpose to minimize the number of cinnamyl groups into one PCL block was to avoid the possible π‐π stacking interactions between closely situated aromatic rings 28 . Such interactions could make the micellar core more compact and to decrease the loading efficiency as reported for PEO‐b‐PLA (polylactide) copolymers bearing cinnamyl groups 29 …”

Section: Resultsmentioning

confidence: 99%

“…The purpose to minimize the number of cinnamyl groups into one PCL block was to avoid the possible π-π stacking interactions between closely situated aromatic rings. 28 Such interactions could make the micellar core more compact and to decrease the loading efficiency as reported for PEO-b-PLA (polylactide) copolymers bearing cinnamyl groups. 29 The synthesized PEO-b-P(PrCL-co-CL) block copolymers were characterized by 1 H-NMR analysis (Figure 1) and the data were used to calculate the composition and number-average molar mass (M n ).…”

Section: Synthesis and Characterization Of Diblock Copolymersmentioning

confidence: 99%

Poly(ethylene oxide)‐block‐poly(α‐cinnamyl‐ε‐caprolactone‐co‐ε‐caprolactone) diblock copolymer nanocarriers for enhanced solubilization of caffeic acid phenethyl ester

Atanasova

Grancharov

Petrov

2020

Journal of Polymer Science

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We report novel micellar carriers, comprising pendant cinnamyl moieties in the core-forming block, designed to increase the solubilization of caffeic acid phenethyl ester (CAPE) in aqueous media. Amphiphilic poly(ethylene oxide)block-poly(α-cinnamyl-ε-caprolactone-co-ε-caprolactone) (PEO-b-P(CyCL-co-CL) diblock copolymers were synthesized by ring-opening copolymerization of α-propargyl-ε-caprolactone and ε-caprolactone from a monofunctional PEO macroinitiator and subsequent attachment of cinnamyl groups via click reaction. In addition, a linear PEO-b-PCL diblock copolymer was synthesized and used in this study for comparison. Next, nanosized micelles from PEO-b-P (CyCL-co-CL) and PEO-b-PCL were formed via the solvent evaporation method and then loaded with CAPE. Dynamic and electrophoretic light scattering, and transmission electron microscopy were used to characterize both blank and loaded carriers. The potential of the micelles comprising pendant cinnamyl group to solubilize CAPE in water was evaluated in a comparative fashion to that of nonmodified PEO-b-PCL diblock copolymer.

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“…The antioxidant potential of hesperitin derivatives was performed by DPPH method evaluated in the form of IC 50 estimated using the ELISA plate reader EPOCH™ “MICROPLATE READER (BIOTEK)”. This method opted for evaluation of free radical scavenging activity of DPPH was base on modified procedure described by Dhiman et al [33]. The tested compounds were prepared in methanolic solution and reacted with methanolic solution of DPPH at 37 °C.…”

Section: Methodsmentioning

confidence: 99%

In silico design and synthesis of hesperitin derivatives as new xanthine oxidase inhibitors

2019

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Background Hesperitin, a naturally occurring flavonoid was hybridized with phenolic acids to evaluate its potential to inhibit the activity of xanthine oxidase (XO), a key enzyme which catalyses xanthine to uric acid which is found to be associated with gout and many life style related disorders. Objective To develop new xanthine oxidase inhibitors from natural constituents along with antioxidant potential. Method In this report, we designed and synthesized hesperitin derivatives hybridized with natural phenolic acids to form ester linkage with the help of molecular docking. The synthesized compounds were evaluated for their antioxidant and xanthine oxidase inhibitory potential. Results The in vitro xanthine oxidase inhibitory activity and enzyme kinetics studies showed that hesperitin derivatives displayed a potential inhibition against XO in competitive manner with IC 50 value ranging from 9.0 to 23.15 µM and HET4 was revealed as most active derivative. Molecular simulation revealed that new hesperitin derivatives interacted with the amino acid residues SER1080, PHE798, GLN1194, ARG912, THR1083, ALA1078 and MET1038 located within the active cavity of XO. Results of antioxidant activity revealed that all the derivatives showed very good antioxidant potential. Conclusion Taking advantage of molecular docking, this hybridization of two natural constituent could lead to desirable xanthine oxidase inhibitors with improved activity.

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Synthesis and biological evaluation of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives

Cited by 12 publications

References 20 publications

In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors

In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors

Poly(ethylene oxide)‐block‐poly(α‐cinnamyl‐ε‐caprolactone‐co‐ε‐caprolactone) diblock copolymer nanocarriers for enhanced solubilization of caffeic acid phenethyl ester

In silico design and synthesis of hesperitin derivatives as new xanthine oxidase inhibitors

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