1154-77-4Relevant articles and documents
Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines
Villena, Joan,Montenegro, Iván,Said, Bastian,Werner, Enrique,Flores, Susana,Madrid, Alejandro
, (2021)
This work reports on the development of an efficient and ecofriendly ultrasound assisted method for the high yield synthesis (70.0–94.0%) of eighteen oxyalkylated derivatives of 2′,4′-dihydroxychalcone. Synthesized compounds were subjected to in vitro biological assays against HT-29 (colorectal), MCF-7 (breast), and PC-3 (prostate) human tumor cell lines, these cell lines are among the ten most aggressive malignancies diagnosed in the world. Cytotoxicity evaluations showed that four of the synthesized compounds exhibited moderate to very high toxic activity against MCF-7 (IC50 = 8.4–34.3 μM) and PC-3 (IC50 = 9.3–29.4 μM) – comparable to 5-fluorouracil (IC50 16.4–22.3 μM). The same compounds only showed moderate activity against HT-29 (IC50 15.3–36.3 μM), closer to daunorubicin (IC50 15.1 μM). Next, although selectivity index (SI) of compounds was weak, compound 18 exhibited a remarkable and selective cytotoxic activity (5.8–10.57) against cancer cells. Outside of these, most compounds significantly reduced cell survival, increased reactive oxygen species (ROS) and caspase activity, and decreased mitochondrial membrane permeability. In this sense, a portion of anti-proliferative activity is due to apoptosis. Notwithstanding, due to its remarkable response, chalcone 18 may be a potential alternative as a chemotherapeutic anti-carcinogen.
Synthesis, molecular docking and α-glucosidase inhibitory activity study of 2,4,6-triaryl pyrimidine derivatives
Abdollahi, Mohammad,Amini, Mohsen,Bule, Mohammed Hussen,Esfandyari, Roghaieh,Faramarzi, Mohammad Ali,Tafesse, Tadesse Bekele
, p. 1216 - 1226 (2020/10/06)
Background: α-Glucosidase inhibitors hinder the carbohydrate digestion and play an important role in the treatment of diabetes mellitus. α-glucosidase inhibitors available on the market are acarbose, miglitol, and voglibose. However, the use of acarbose is diminishing due to related side effects like diarrhea, bloating and abdominal distension. Objectives: This study aimed to synthesize 2,4,6-triaryl pyrimidines derivatives, screen their α-glucosidase inhibitory activity, perform kinetic and molecular docking studies. Methods: A series of 2,4,6-triaryl pyrimidine derivatives were synthesized and their α-glucosidase inhibitory activity was screened in vitro. Pyrimidine derivatives 4a-m were synthesized via a two-step reaction with a yield between 49 and 93%. The structure of the synthesized compounds was confirmed by different spectroscopic techniques (IR, NMR and MS). The in vitro α-glucosidase inhibition activities of the synthesized compounds 4a-m was also evaluated against Saccharomyces cerevisiae α-glucosidase. Results and Discussion: The majority of synthesized compounds had α-glucosidase inhibitory activity. Particularly compounds 4b and 4g were the most active compounds with an IC50 value of 125.2± 7.2 and 139.8 ± 8.1 μM respectively. The kinetic study performed for the most active compound 4b revealed that the compound was a competitive inhibitor of Saccharomyces cerevisiae α-glucosidase with Ki of 122 μM. The molecular docking study also revealed that the two compounds have important binding interactions with the enzyme active site. Conclusion: 2,4,6-triarylpyrimidine derivative 4a-m were synthesized and screened for α-glucosidase inhibitory activity. Most of the synthesized compounds possess α-glucosidase inhibitory activity, and compound 4b demonstrated the most significant inhibitory action as compared to acarbose.
QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase
Yaeghoobi, Marzieh,Frimayanti, Neni,Chee, Chin Fei,Ikram, Kusaira K.,Najjar, Belal O.,Zain, Sharifuddin M.,Abdullah, Zanariah,Wahab, Habibah A.,Rahman, Noorsaadah Abd.
, p. 2133 - 2142 (2016/10/25)
Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.
