A fluorine scan of a tubulin polymerization inhibitor isocombretastatin A-4: Design, synthesis, molecular modelling, and biological evaluation was written by Naret, Timothee;Bignon, Jerome;Bernadat, Guillaume;Benchekroun, Mohamed;Levaique, Helene;Lenoir, Christine;Dubois, Joelle;Pruvost, Alain;Saller, Francois;Borgel, Delphine;Manoury, Boris;Leblais, Veronique;Darrigrand, Romain;Apcher, Sebastien;Brion, Jean-Daniel;Schmitt, Etienne;Leroux, Frederic R.;Alami, Mouad;Hamze, Abdallah. And the article was included in European Journal of Medicinal Chemistry in 2018.HPLC of Formula: 95668-20-5 This article mentions the following:
A novel series of tubulin polymerization inhibitors, based on fluorinated derivatives of isocombretastatin A-4 (isoCA-4), was synthesized with the goal of evaluating the effect of these compounds on the proliferative activity. The introduction of fluorine atom was performed on the Ph ring or at the linker between the two aromatic rings. The modification of isoCA-4 by introduction of difluoromethoxy group at the para-position, I, and substitution of the two protons of the linker by two fluorine atoms, II, produced the most active compounds in the series, with IC50 values of 0.15-2.2 nM (for I) and 0.1-2 nM (for II), resp., against a panel of six cancer cell lines. Compounds I and II had greater antiproliferative activity in comparison with references combretastatin A-4 (CA-4) or isoCA-4; the presence of fluorine group leads to a significant enhancement of the antiproliferative activity. Mol. docking studies indicated that compounds I and II occupy the colchicine binding site of tubulin. Evaluation of cytotoxicity in Human noncancer cells indicated that the compounds I and II were practically ineffective in quiescent peripheral blood lymphocytes, and may have a selective antiproliferative activity against cancer cells. Analyses of cell cycle distribution, and morphol. microtubules organization showed that compound II induced G2/M phase arrest and, dramatically disrupted the microtubule network. In the experiment, the researchers used many compounds, for example, 3-Nitro-4-(trifluoromethoxy)bromobenzene (cas: 95668-20-5HPLC of Formula: 95668-20-5).
3-Nitro-4-(trifluoromethoxy)bromobenzene (cas: 95668-20-5) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.HPLC of Formula: 95668-20-5
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary