Tricyclic pharmacophore-based molecules as novel integrin αvβ3 antagonists. Part IV: Preliminary control of αvβ3 selectivity by meta-oriented substitution was written by Kubota, Dai;Ishikawa, Minoru;Ishikawa, Midori;Yahata, Naokazu;Murakami, Shoichi;Fujishima, Kazuyuki;Kitakaze, Masafumi;Ajito, Keiichi. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Formula: C8H6BrFO2 This article mentions the following:
To establish the in vivo efficacy of αvβ3/αIIbβ3 dual antagonists possessing a tricyclic pharmacophore, a corresponding αvβ3-selective antagonist was required as a control. We initially took two synthetic approaches to obtain αvβ3-selective antagonists based on the RGD recognition pattern or on modification of the dihedral angle between the central benzene ring and the adjacent heterocycle, but both proved unsuccessful. However, synthesis of novel antagonists with meta-substitution of the central benzene ring generated weak selectivity for αvβ3 over αIIbβ3 for the first time in the family of compounds with the tricyclic pharmacophore. Optimization of meta-oriented antagonists furnished an αvβ3-selective antagonist exhibiting inhibitory activity not only in a receptor-binding assay, but also in a cell adhesion assay. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8Formula: C8H6BrFO2).
Methyl 3-bromo-5-fluorobenzoate (cas: 334792-52-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Formula: C8H6BrFO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary