111425-75-3Relevant articles and documents
Aurones and Analogues: Promising Heterocyclic Scaffolds for Development of Antioxidant and Antimicrobial Agents
Irshad,Ali,Iram,Ahamad,Saleem,Saadia,Batool,Kanwal,Tabassum
, p. 1519 - 1527 (2019)
Synthesis of some new multi-functional analogues of 2′-hydroxy chalcone containing isoxazole and pyrazole functions were synthesized, and their pharmacological activity was tested. Chalcone derivatives were synthesized by the reaction of 2′-hydroxy acetophenone with various substituted benzaldehydes in a basic medium. Aurones were isolated upon treatment with mercuric acetate. Synthesized chalcones and aurones were converted into the corresponding isoxazole and pyrazole derivatives upon their reaction with hydroxylamine hydrochloride or hydrazine hydrate, respectively. Structures of the compounds were confirmed by spectroscopic methods. All synthesized compounds were tested for antioxidant and antibacterial potential. Some of those demonstrated excellent antioxidant activity, and one product was identified as a promising antimicrobial candidate.
NHC-catalyzed reaction of enals with hydroxy chalcones: Diastereoselective synthesis of functionalized coumarins
Bhunia, Anup,Patra, Atanu,Puranik, Vedavati G.,Biju, Akkattu T.
, p. 1756 - 1759 (2013)
The N-heterocyclic carbene-catalyzed annulation of enals with 2′-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.
Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
Ashraf, Jamshaid,Mughal, Ehsan Ullah,Sadiq, Amina,Bibi, Maryam,Naeem, Nafeesa,Ali, Anser,Massadaq, Anam,Fatima, Nighat,Javid, Asif,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Nazar, Muhammad Faizan,Mumtaz, Amara,Tahir, Muhammad Nawaz,Mirzaei, Masoud
, p. 7107 - 7122 (2020/08/21)
To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.
Multitarget 2′-hydroxychalcones as potential drugs for the treatment of neurodegenerative disorders and their comorbidities
?akelj, Simon,Abin-Carriquiry, Juan Andrés,Carvalho, Diego,Colettis, Natalia,Gobec, Stanislav,Higgs, Josefina,Kamecki, Fabiola,Knez, Damijan,Marcos, Alejandra,Marcucci, Carolina,Marder, Mariel,Rademacher, Marina,de Tezanos Pinto, Felicitas
, (2021/10/19)
The complex nature of neurodegenerative diseases (NDDs), such as Alzheimer's disease (AD) and Parkinson's disease (PD) calls for multidirectional treatment. Restoring neurotransmitter levels by combined inhibition of cholinesterases (ChEs) and monoamine oxidases (MAOs, MAO-A and MAO-B), in conjunction with strategies to counteract amyloid β (Aβ) aggregation, may constitute a therapeutically strong multi-target approach for the treatment of NDDs. Chalcones are a subgroup of flavonoids with a broad spectrum of biological activity. We report here the synthesis of 2′-hydroxychalcones as MAO-A and MAO-B inhibitors. Compounds 5c (IC50 = 0.031 ± 0.001 μM), 5a (IC50 = 0.084 ± 0.003 μM), 2c (IC50 = 0.095 ± 0.019 μM) and 2a (IC50 = 0.111 ± 0.006 μM) were the most potent, selective and reversible inhibitors of human (h)MAO-B isoform. hMAO-B inhibitors 1a, 2a and 5a also inhibited murine MAO-B in vivo in mouse brain homogenates. Molecular modelling rationalised the binding mode of 2′-hydroxychalcones in the active site of hMAO-B. Additionally, several derivatives inhibited murine acetylcholinesterase (mAChE) (IC50 values from 4.37 ± 0.83 μM to 15.17 ± 6.03 μM) and reduced the aggregation propensity of Aβ. Moreover, some derivatives bound to the benzodiazepine binding site (BDZ-bs) of the γ-aminobutyric acid A (GABAA) receptors (1a and 2a with Ki = 4.9 ± 1.1 μM and 5.0 ± 1.1 μM, respectively), and exerted sedative and/or anxiolytic like effects on mice. The biological results reported here on 2′-hydroxychalcones provide an extension to previous studies on chalcone scaffold and show them as a potential treatment strategy for NDDs and their associated comorbidities.
