100753-41-1Relevant academic research and scientific papers
Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substituted resorcinol moiety
Khatib, Soliman,Nerya, Ohad,Musa, Ramadan,Shmuel, Maayan,Tamir, Snait,Vaya, Jacob
, p. 433 - 441 (2005)
Chalcones with tetra-substituted hydroxyl groups were synthesized and tested as tyrosinase inhibitors towards designing novel whitening agents, resulting with the most potent inhibitor, with IC50 of 0.02 μM concn. Compounds, which inhibit tyrosinase, could be effective as depigmenting agents. We have introduced a group of mono-, di-, tri- and tetra-substituted hydroxychalcones as effective tyrosinase inhibitors, showing that the most important factor determining tyrosinase inhibition efficiency is the position of the hydroxyl group(s) rather their number. The aim of the present study was to investigate the contribution of the different functional groups of the tetrahydroxychalcones to their inhibitory potency, with a view to optimizing the design of whitening agents. Four tetrahydroxychalcones were evaluated, the commercially available Butein and other three were synthesized, and their inhibitory effect on tyrosinase was tested. Results showed that a 2,4-substituted resorcinol subunit on ring B contributed the most to inhibitory potency. Changing the resorcinol substitute to position 3,5- or placing it on ring A significantly diminished the inhibitory effect of the compounds. A catechol subunit on ring A acted as a metal chelator (in the presence of copper ions) and as a competitive inhibitor (in the presence of tyrosinase), while a catechol on ring B oxidized to o-quinone (in the presence of both copper ions and tyrosinase). Three of the compounds also demonstrated antioxidant activity, which may contribute to the prevention of pigmentation. An examination of correlations between inhibitory activity and physical properties of the chalcones tested (such as dissociation energy and molecular planarity) showed positive correlation with the moment dipole value in the Y-axis, which may be used as an indicator of the inhibitory potential of new molecules. The present study revealed two very active tyrosinase inhibitors, 2,4,3′,4′- hydroxychalcone and 2,4,2′,4′-hydroxychalcone (with IC50 of 0.2 and 0.02 μM, respectively). Structure-related activity studies added some understanding of the role and contribution of different functional groups associated with tyrosinase inhibitors.
Biological evaluation of non-basic chalcone CYB-2 as a dual ABCG2/ABCB1 inhibitor
Cai, Chao-Yun,Chen, Zhe-Sheng,Gupta, Pranav,Lei, Zi-Ning,Tan, Cai-Ping,Wang, Bo,Wang, Jing-Quan,Wang, Yi-Jun,Zhang, Wei,Zhang, Yun-Kai
, (2020)
The enhancement of drug efflux caused by ATP-binding cassette (ABC) transporters (including ABCG2 and ABCB1) overexpression is an important factor for multidrug resistance (MDR) in cancers. After testing the reversal activities of 19 chalcone and bis-chal
Mechanistic investigations on substituted benzene sulphonamides as apoptosis inducing anticancer agents
Mettu, Akhila,Naikal James Prameela, Subhashini,Talla, Venu,Thumma, Soujanya
, (2020/01/28)
In an approach to develop potent cytotoxic compounds with targeted action, a systematic methodology was employed to design and initially synthesize parent compounds A1, A8, A13 and A14 followed by synthesis of further analogs of A1 (A2-A7) and A8 (A9-A12)
Identification and validation of small molecule modulators of the NusB-NusE interaction
Cossar, Peter J.,Ma, Cong,Gordon, Christopher P.,Ambrus, Joseph I.,Lewis, Peter J.,McCluskey, Adam
supporting information, p. 162 - 167 (2016/12/27)
Formation of highly possessive antitermination complexes is crucial for the efficient transcription of stable RNA in all bacteria. A key step in the formation of these complexes is the protein-protein interaction (PPI) between N-utilisation substances (Nu
Effect on acetylcholinesterase and anti-oxidant activity of synthetic chalcones having a good predicted pharmacokinetic profile
Sakata, Renata P.,Figueiró, Micheli,Kawano, Daniel F.,Almeida, Wanda P.
, p. 654 - 663 (2018/02/02)
Background: Acetylcholinesterase (AChE) is an important target in the development of drug to treat Alzheimer's disease (AD). In this work, we investigated the effect of twenty-two synthesized chalcones on AChE activity. Objective: This work is aimed to synthesize and evaluate the effect of chalcones on the AChE activity, as well as anti-oxidant activity and predict their pharmacokinetic profile. Method: Chalcones were synthesized through a Claisen-Schmidt condensation and their inhibitory effect on the AChE was evaluated by the Elmann's colorimetric method. To determine the anti-oxidant activity the DPPH radical scavenging method was chosen. Results: We found that all chalcones inhibit this activity, with IC50 values ranging from 0.008 to 4.8 μM. We selected the most active compound 19 with an IC50 value of 0.008 μM for a kinetic study demonstrating a competitive inhibition mode. Molecular docking simulations showed a good interaction between 19 and the active site of AChE. Considering the prediction of pharmacokinetic parameters being a useful tool for selecting potential drug candidates, our study results suggest that the majority of chalcones, including the most active one, have a promising pharmacokinetic profile and blood-brain barrier permeability. The involvement of reactive oxygen species (ROS) in AD-related events has encouraged us to evaluate these chalcones as radical scavengers. Conclusion: We have found that compound 19 is a potent AChE inhibitor, and based on kinetic studies, it acts as a competitive inhibitor.
Synthesis, cytotoxic properties and tubulin polymerization inhibitory activity of novel 2-pyrazoline derivatives
Abdel-Aziz, Mohamed,Aly, Omar M.,Khan, Sabine S.,Mukherjee, Kamalika,Bane, Susan
scheme or table, p. 535 - 548 (2012/09/08)
A series of novel 1-(3',4',5'-trimethoxybenzoyl)-3,5-diarylpyrazoline derivatives were synthesized and evaluated for their cytotoxic properties on different cancer cell lines and tubulin polymerization inhibitory activity. Compounds 6d and 6e exhibited re
Evaluation and discovery of novel synthetic chalcone derivatives as anti-inflammatory agents
Wu, Jianzhang,Li, Jianling,Cai, Yuepiao,Pan, Yong,Ye, Faqing,Zhang, Yali,Zhao, Yunjie,Yang, Shulin,Li, Xiaokun,Liang, Guang
experimental part, p. 8110 - 8123 (2012/01/07)
Major anti-inflammatory agents, steroids and cyclooxygenase, were proved to have serious side effects. Here, a series of chalcone derivatives were synthesized and screened for anti-inflammatory activities. QSAR study revealed that the presence of electron-withdrawing groups in B-ring and electron-donating groups in A-ring of chalcones was important for inhibition of LPS-induced IL-6 expression. Further, compounds 22, 23, 26, 40, and 47 inhibited TNF-α and IL-6 release in a dose-dependent manner and decreased LPS-induced TNF-α, IL-1β, IL-6, IL-12, and COX-2 mRNA production. Mechanistically, compounds 23 and 26 interfered with JNK/NF-κB signaling and dose-dependently prevented ERK and p38 activation. In addition, 23 and 26 exhibited a significant protection against LPS-induced death and were able to block high glucose-activated cytokine profiles in macrophages. Together, these data show a series of anti-inflammatory chalcones with potential therapeutic effects in inflammatory diseases.
Synthesis and investigation of anti-inflammatory activity and gastric ulcerogenicity of novel nitric oxide-donating pyrazoline derivatives
Shoman, Mai E.,Abdel-Aziz, Mohamed,Aly, Omar M.,Farag, Hassan H.,Morsy, Mohamed A.
scheme or table, p. 3068 - 3076 (2009/10/02)
A group of 3,5-diaryl-2-pyrazoline derivatives were prepared via the reaction of various chalcones with hydrazine hydrate in ethanol. A group of NO-donating-2-pyrazoline derivatives were synthesized by carrying a nitrate ester group or an oxime group onto
