Experimental Reactivity Parameters for Toxicity Modeling: Application to the Acute Aquatic Toxicity of SN2 Electrophiles to Tetrahymena pyriformis was written by Roberts, David W.;Schultz, T. Wayne;Wolf, Erika M.;Aptula, Aynur O.. And the article was included in Chemical Research in Toxicology in 2010.Synthetic Route of C18H11BrO The following contents are mentioned in the article:
A diverse set of 60 haloaliph. compounds were evaluated for reactivity with cysteine thiol groups in the previously described RC50 assay using glutathione (GSH) as a model nucleophile. Reactivity was quantified by the RC50 value, the concentration of test compound that produced 50% reaction of the GSH thiol groups in 120 min. Under standard conditions, RC50 values are math. proportional to reciprocal rate constants Quant. structure-activity relationship (QSAR) anal. correlating acute aquatic toxicity (IGC50) to Tetrahymena pyriformis with RC50 values was carried out. It was found that subdivision of the compounds into subdomains according to their reaction mechanism characteristics enabled toxicity-reactivity relationships to be identified. The largest subdomain consisting of 22 compounds in which a primary halogen is α to a carbonyl or other electroneg. unsaturated group and which can be confidently assigned as SN2 electrophiles fits the equation pIGC50 (mM) = 0.94 (±0.07) pRC50 (mM) + 1.34 (±0.07), n = 22, r2 = 0.889, r2(adj) = 0.884, s = 0.27, and F = 161. Compounds in which the halogen is not α to an unsaturated group are not reactive in the GSH assay and do not exhibit reactive toxicity to T. pyriformis. Compounds tested in which the halogen is α to an unsaturated nonelectroneg. group were found to be less toxic in the assay than predicted by the above QSAR equation. Within a subdomain of 21 compounds having a halogen α to an electroneg. unsaturated group that, in the absence of exptl. evidence, could not be confidently assigned as SN2 electrophiles, 2-bromoalkanoates of general structure R1CHBrCO2R2, 2-bromopropionamide, and 2-haloalkanoic acids of general formula R1CHXCO2H (nine compounds in total) are all well-predicted by the above equation. Of the other 12 compounds of this subdomain, eight are substantially less toxic than predicted by the above equation and are considered to react differently, whereas the α-halonitriles (four compounds) are more toxic than predicted and fit a correlation of their own: pIGC50 = 1.01 (±0.05) pRC50 + 2.04 (±0.05), n = 4, r2 = 0.995, r2(adj) = 0.992, s = 0.08, and F = 381, with a similar slope but larger intercept. An explanation in terms of their phys. chem. and possible involvement of released cyanide ion is suggested. This study involved multiple reactions and reactants, such as 2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5Synthetic Route of C18H11BrO).
2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). 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 C18H11BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary