154479-31-9

Upstream product

• 54696-05-8 4'-benzyloxy-acetophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 100-39-0 benzyl bromide 

Downstream Products

• 154479-40-0 1-(4-benzyloxyphenyl)-3-(4-chlorophenyl)-2-phenylthiolpropan-1-one 
• 154479-37-5 1-(4-benzyloxyphenyl)-2-bromo-3-(4-chlorophenyl)propan-1-one 
• 154479-43-3 2-(4-chlorobenzyl)-3-(4-hydroxyphenyl)benzothiophene 
• 154479-34-2 1-(4-benzyloxyphenyl)-3-(4-chlorophenyl)propan-1-one 

Relevant academic research and scientific papers

Synthesis and evaluation of modified chalcone based p53 stabilizing agents

Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to various cellular stresses thereby preventing cancer development. Activation and stabilization of p53 through small organic molecules is, therefore, an attractive approach for the treatment of cancers retaining wild-type p53. In this context, a series of nineteen chalcones with various substitution patterns of functional groups including chloro, fluoro, methoxy, nitro, benzyloxy, 4-methyl benzyloxy was prepared using Claisen-Schmidt condensation. The compounds were characterized using NMR, HRMS, IR and melting points. Evaluation of synthesized compounds against human colorectal (HCT116) and breast (CAL-51) cancer cell lines revealed potent antiproliferative activities. Nine compounds displayed GI50 values in the low micromolar to submicromolar range; for example (E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (SSE14108) showed GI50 of 0.473 ± 0.043 μM against HCT116 cells. Further analysis of these compounds revealed that (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (SSE14105) and (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (SSE14106) caused rapid (4 and 8-h post-treatment) accumulation of p53 in HCT116 cells similar to its induction by positive control, Nutlin-3. Such activities were absent in 3-(4-methoxyphenyl)propiophenone (SSE14106H2) demonstrating the importance of conjugated ketone for antiproliferative and p53 stabilizing activity of the chalcones. We further evaluated p53 levels in the presence of cycloheximide (CHX) and the results showed that the p53 stabilization was regulated at post-translational level through blockage of its degradation. These chalcones can, therefore, act as fragment leads for further structure optimization to obtain more potent p53 stabilizing agents with enhanced anti-proliferative activities.

Chalcones: A valid scaffold for monoamine oxidases inhibitors

A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar ranges, the best results were obtained in the presence of chlorine and hydroxyl or methoxyl substituents. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAO-B, molecular modeling studies were carried out on new, high resolution, hMAO-B crystallographic structures. For the only compound that also showed activity against hMAO-A as well as low selectivity, the molecular modeling study was also performed on the hMAO-A crystallographic structure. The docking technique provided new insight on the inhibition mechanism and the rational drug design of more potent/selective hMAO inhibitors based on the chalcone scaffold.

Synthesis of 2-(4-halogenobenzyl)-3-arylbenzothiophenes and a 2-(4-fluorobenzyl)-3-arylbenzoselenophene as Selective Ligands for Antiestrogen-Binding Sites

Several basic ethers of 2-halogenobenzyl-3-arylbenzothiophenes and a 2-(4-fluorobenzyl)-3-arylbenzoselenophene have been synthesized in good yields in a 5-step sequence from the readily available corresponding chalcones.The key step in the synthesis