38767-64-5Relevant academic research and scientific papers
Synthesis and structure-activity relationships of chalcone derivatives as inhibitors of ovarian cancer cell growth
Tucker, Zachary D.,Barrios, Francis J.,Krzysiak, Amanda J.
, p. 1259 - 1266 (2017/11/14)
Background: Ovarian cancer remains a disease with a poor five year survival rate. As such, novel therapies are needed. Natural chalcones as well as their synthetic derivatives have shown biological activity in a number of areas including the inhibition of cancer cell growth. Objective: To synthesize a library of chalcone derivatives, including novel structures, and determiner the inhibition of ovarian cancer cell growth and Structure-activity-relationships. Methods: The Claisen-Schmidt condensation reaction between substituted acetophenones and aromatic aldehydes was used to produce a series of novel chalcones in moderate to excellent yields and good purity. Cellular proliferation of CA-OV3 cells was measured with a MTS assay. Results: Out of the thirty-four synthesized compounds, eight are new derivatives. The synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation of these β-phenylacrylophenone derivatives in CA-OV3 cells showed interesting antiproliferative activities providing initial structure – activity information. Conclusion: Fourteen of the thirty-four tested compounds showed significant activity, with several showing near complete inhibition of growth at 100 μM. The structure-activity relationships suggest that modification to the A ring is widely tolerated and that electron-donating modifications to the B ring are beneficial to activity. Electron-withdrawing modifications to the B ring did not show inhibition of cell growth.
Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
Winter, Evelyn,Chiaradia, Louise Domeneghini,De Cordova, Clarissa A.S.,Nunes, Ricardo José,Yunes, Rosendo Augusto,Creczynski-Pasa, Tania Beatriz
experimental part, p. 8026 - 8034 (2011/02/22)
In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms.
Tetrachlorosilane-zinc chloride as a new potent binary reagent for one-pot, three-component synthesis of mannich-type products
Badawy, Doria S.,Abdel-Galil, Ebrahim,Kandeel, Ezzat M.,Basyouni, Wahid M.,Khatab, Tamer K.
experimental part, p. 2799 - 2812 (2010/04/03)
A combination of tetrachlorosilane and zinc chloride in dichloromethane as an efficient and ambient binary reagent to promote a one-pot amidoalkylation reaction of enolizable ketones, aromatic aldehydes with acetonitriles, or benzonitrile have been develo
Synthesis and biological evaluation of aromatic enones related to curcumin
Robinson, Thomas Philip,Hubbard IV, Richard B.,Ehlers, Tedman J.,Arbiser, Jack L.,Goldsmith, David J.,Bowen, J. Phillip
, p. 4007 - 4013 (2007/10/03)
Curcumin, a natural product isolated from the spice turmeric, has been shown to exhibit a wide range of pharmacological activities including certain anti-cancer properties. It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or exceed curcumin's ability to inhibit endothelial cell growth in vitro. Due to both their commercial availability and their fairly straightforward synthetic preparation, these low molecular weight compounds are attractive leads for developing future angiogenic inhibitors.
Chiral Recognition and Molecular Interaction in Cellulose Derivatives
Itoh, Kenji,Ikeda, Tomiki,Tazuke, Shigeo,Shibata, Tohru
, p. 5759 - 5765 (2007/10/02)
Nineteen 1,3-bis(aryl)propane derivatives and six model compounds with a single chromophore were used to explore the chiral discrimination ability of cellulose derivatives, in particular cellulose triphenylcarbamate (CTC), in connection with the mode of interaction of these probe molecules with adsorbents.The interaction was evaluated by conformational analysis of the probe molecules and circular dichroism.The 1,3-bis(aryl)propanes with 9-anthryl moieties possessed a highly limited conformation owing to the bulky substituent and hardly changed their shape on CTCas evidenced by CD spectra; thus, they may be regarded as "rigid" substrates.However, these "rigid" substrates were resolved quite effectively.On the other hand, those with 2-naphthyl moieties possessed a number of stable conformations and could change their shape in diastereomeric complexes on CTC; thus, they may be assumed as "soft" substrates, against which the chiral discrimination was inefficient.The present study revealed that the optical resolution may be interpreted at least partly in terms of the "rigid" and "soft" concept.
