Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters was written by Pokorny, Jan;Olejnikova, Denisa;Frydrych, Ivo;Liskova, Barbora;Gurska, Sona;Benicka, Sandra;Sarek, Jan;Kotulova, Jana;Hajduch, Marian;Dzubak, Petr;Urban, Milan. And the article was included in European Journal of Medicinal Chemistry in 2021.Synthetic Route of C8H7BrO2 This article mentions the following:
A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Four compounds had IC50 below 5婵炴挾鎸紀l/L; I and II were selected for studies of the mechanism of action. Cell cycle anal. revealed an increase in the number of apoptotic cells at 5 x IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both I and II led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 x IC50 and almost complete inhibition at 5 x IC50. Interestingly, compound II at 5 x IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds I and II trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacol. parameters of derivative I were superior to II, therefore I was the finally selected candidate for the development of anticancer drug. In the experiment, the researchers used many compounds, for example, 3-(Bromomethyl)benzoic acid (cas: 6515-58-8Synthetic Route of C8H7BrO2).
3-(Bromomethyl)benzoic acid (cas: 6515-58-8) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon闂佺偨鍎茶ぐ绲﹐mine bond is electrophilic, i.e. alkyl bromides are alkylating agents. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Synthetic Route of C8H7BrO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary