Halogenated Bis(methoxybenzylidene)-4-piperidone Curcuminoids with Improved Anticancer Activity was written by Schmitt, Florian;Subramaniam, Dharmalingam;Anant, Shrikant;Padhye, Subhash;Begemann, Gerrit;Schobert, Rainer;Biersack, Bernhard. And the article was included in ChemMedChem in 2018.Formula: C8H6Br2O2 This article mentions the following:
A series of readily available curcuminoids with a halogenated bis(4-methoxy/4,5-dimethoxybenzylidene)-4-piperidone structure were prepared and analyzed for their cytotoxic impact on eight human cancer cell lines of five different entities. The known 3,4,5-trimethoxybenzylidene curcuminoid 2a and the new bis-(3-bromophenyl) and bis-(3,5-dibromophenyl) derivatives 3c ((E)-1-ethyl-3,5-bis(3-bromo-4,5-dimethoxybenzylidene)-4-piperidone HCl) and 3d ((E)-1-ethyl-3,5-bis(3,5-dibromo-4-methoxybenzylidene)-4-piperidone HCl) proved to be more strongly antiproliferative than the known curcuminoid EF24 against six of these cell lines. Compounds 2a and 3c caused a distinct increase of reactive oxygen species, which eventually elicited apoptosis in 518A2 melanoma cells. Compound 2a arrested 518A2 melanoma cells in G1 phase of the cell cycle and had no effect on the expression of pro-metastatic matrix metalloproteinases MMP-2 and MMP-9, whereas 3c led to an accumulation of 518A2 cells in the G2/M phase and to a downregulation of MMP-2 expression. In addition, treatment with 2a and 3c resulted in significant inhibition of colony formation in HCT116 cells. Both 2a and 3c showed antiangiogenic activity, for example, by inhibiting the formation of sub-intestinal veins (SIV) in zebrafish embryos. Compound 3c was also well tolerated by mice and inhibited the growth of HCT116 colon cancer xenografts. In the experiment, the researchers used many compounds, for example, 3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1Formula: C8H6Br2O2).
3,5-Dibromo-4-methoxybenzaldehyde (cas: 108940-96-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Formula: C8H6Br2O2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary