Synthesis of new heterocyclic hybrids based on pyrazole and thiazolidinone scaffolds as potent inhibitors of tyrosinase

Gawande, Shrikant S.; Warangkar, Suchita C.; Bandgar, B. P.; Khobragade, Chandrahasya N.

doi:10.1016/j.bmc.2012.12.053

Cited by 39 publications

(21 citation statements)

References 26 publications

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“…The high resolution (HR)-MS electrospray ionization (ESI)-MS spectra of compounds displayed molecular ion peaks distinctive to their molecular masses. Taken together, the structures of synthesized α,β-unsaturated carbonyl compounds (3)(4)(5)(6)(7)(8)(9)(10) were confirmed by the presence of IR and NMR peaks characteristic to α,β-unsaturation, along with the presence of molecular ion peaks corresponding to the molecular masses of the synthesized compounds.…”

Section: Resultsmentioning

confidence: 72%

“…The UV spectra of compounds (3-10) demonstrated two typical chalcone bands, the band-I at 441.50-347.00 nm and band-II at 270.50-239.50 nm. The IR spectra of compounds (3)(4)(5)(6)(7)(8)(9)(10) H-NMR spectrum of 3-phenylallylidene substituted compound 8, =CH proton appeared upfield and as a doublet due to the presence of neighbouring Ar-CH=CH-group. The total number of protons in the 1 H-NMR spectra of compounds were consistent with their respective protons of molecular formulas.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the development of tyrosinase inhibitors has gradually become more important as skin whitening agents and preservatives in cosmetic and food industry, respectively, 4,5) and research in this area is continuously growing. [6][7][8][9][10][11][12][13] Many tyrosinase inhibitors have already been reported from both synthetic and natural sources, for example hydroquinone, kojic acid, arbutin, retinol, linoleic acid, galangin, and numerous botanical products. 14) However, due to undesirable side effects, many of them are banned in several countries.…”

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confidence: 99%

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Design, Synthesis and Biological Evaluation of Oxindole-Based Chalcones as Small-Molecule Inhibitors of Melanogenic Tyrosinase

Kumar¹,

Bansal²,

Narkhede³

et al. 2017

Chem. Pharm. Bull.

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The enzyme tyrosinase regulates melanogenesis and skin hyperpigmentation by converting L-3,4-dihydroxyphenylalanine (L-DOPA) into dopaquinone, a key step in the melanin biosynthesis. The present work deals with design and synthesis of various oxindole-based chalcones as monophenolase and diphenolase activity inhibitors of tyrosinase. Among the screened compounds, 4-hydroxy-3-methoxybenzylidene moiety bearing chalcone (7) prepared by one pot reaction of oxindole and vanillin displayed the highest activity against tyrosinase with IC 50 s of 63.37 and 59.71 µM in monophenolase and diphenolase activity assays, respectively. In molecular docking studies, chalcone 7 also showed the highest binding affinity towards the enzyme tyrosinase while exhibiting the lowest estimated free energy of binding, among all the ligands docked.Key words tyrosinase inhibitor; oxindole-based chalcone; melanogenesis; molecular docking Tyrosinase is a major enzyme of melanogenic cascade, accountable for hydroxylation of L-tyrosine to L-3,4-dihydroxyphenylalanine (L-DOPA) and subsequent oxidation of L-DOPA to dopaquinone, the significant steps in melanin production.

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Section: Resultsmentioning

confidence: 72%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Design, Synthesis and Biological Evaluation of Oxindole-Based Chalcones as Small-Molecule Inhibitors of Melanogenic Tyrosinase

Kumar¹,

Bansal²,

Narkhede³

et al. 2017

Chem. Pharm. Bull.

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“…For the other hand, heterocyclic scaffolds like quinoline, isoxazole, pyrazole, imidazole, pyridine, pyrimidine, and indole moieties, among others, have special interest within the scope of medicinal chemistry due their versatile reactivity to design synthetic hybrids with potential biological activities [26][27][28][29][30][31][32][33][34][35]. Indeed, indole derivatives have been one of the scaffolds more studied to date in the chemistry of heterocyclic compounds, especially, due to their potent pharmacological properties as natural derivatives [36].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

Treuer

De-la-Torre

Gutiérrez

2017

Journal of Chemistry

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Given the broad spectrum of biological uses of heteroaryl-acrylonitrile derivatives, it is necessary to find simple methods to synthesize and diversify this family of compounds. We report a stereoselective synthesis of a series of new (E)-2-(1H-indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles ( a-i) obtained from 3-(cyanoacetyl)indole and heteroaryl-aldehydes under microwaveassisted Knoevenagel reaction at 300 W of potency and 100 ∘ C. The desired derivatives ( a-i) were obtained with variable yields (30-94%) and time reactions (8-90 min). All the heteroaryl-acrylonitriles were characterized by physicoanalytical techniques such IR, 1 H, 13 C NMR, and electrospray mass spectrometry.

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“…Then after rearrangement and a series metabolic process, they are aggregated into 5,6-dihydroxyindole and indole quinone. Eventually, melanin is formed [7,8]. Throughout the course of producing melanin, tyrosinase which is the main rate-limiting enzyme in formation process of melanin is both served as hydroxylase of tyrosine and dopa oxidase and oxidase of 5,6-dihydroxyindole [9,10].…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Mechanism of Salidroside on Tyrosinase

Zhu¹,

Chen²,

Zhao³

et al. 2014

JFNR

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Tyrosinase is a key rate-limiting enzyme in melanin synthesis which can be blocked to reduce melasma and freckles by inhibiting the activity of tyrosinase. Salidroside showed certain inhibitory effects on tyrosinase by enzyme kinetics with inhibition of 33.04%. Besides it was also a competitive inhibitor of tyrosinase which served as a substrate analogue to combine with enzyme to produce quinones with stronger light absorption. Furthermore, docking results implied that inhibitory mechanisms might be attributed to the weak interactions between salidroside and tyrosinase such as hydrogen bonds and van del waals. Salidroside is a main kind of plant flavonoids from Rhodiola rosea, walnut and so on. Studying inhibitory mechanism of salidroside on tyrosinase is not only helpful for developing anti-freckle products in which salidroside is one of the most important components, but also beneficial for making better use of plant flavonoids to seek for a new generation of natural skin care cosmetics.

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Synthesis of new heterocyclic hybrids based on pyrazole and thiazolidinone scaffolds as potent inhibitors of tyrosinase

Cited by 39 publications

References 26 publications

Design, Synthesis and Biological Evaluation of Oxindole-Based Chalcones as Small-Molecule Inhibitors of Melanogenic Tyrosinase

Design, Synthesis and Biological Evaluation of Oxindole-Based Chalcones as Small-Molecule Inhibitors of Melanogenic Tyrosinase

Synthesis of New (E)-2-(1H-Indole-3-ylcarbonyl)-3-heteroaryl-acrylonitriles via Microwave-Assisted Knoevenagel Condensation

Inhibitory Mechanism of Salidroside on Tyrosinase

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