Disease relevance of Bromoethylene

• Two general approaches have been established for the synthesis of these compounds, based on dehydration of benzhydryl alcohols (7) and Suzuki coupling reactions of vinyl bromide (8), and are herewith reported [1].
• The genetic toxicity profiles of vinyl chloride (VCl), vinyl bromide (VBr), ethyl carbamate (EC), vinyl carbamate (VC) and some structurally related chemicals were investigated in both somatic and germ cells of Drosophila melanogaster [2].

High impact information on Bromoethylene

• The key step is a free radical cyclization of vinyl bromide 29 to afford 30 [3].
• With I(CL/RL) values (2.7-6.9) similar to those obtained for cross-linking agents, vinyl chloride, vinyl bromide, ethyl carbamate and vinyl carbamate are all efficient clastogenic agents in Drosophila germ cells [2].
• N-Boc deprotection, followed by a one-pot olefin isomerization and intramolecular amine alkylation afforded a bicyclic vinyl bromide that was converted into (+)-elaeokanine A by sequential halogen metal exchange and reaction of the organolithium reagent with N-butanoylmorpholine [4].
• To unambiguously determine the reaction products, three precursors are used to produce the vinyl radical by laser photolysis: vinyl bromide, methyl vinyl ketone, and vinyl iodide [5].
• Vinyl bromide yielded DNA damage in all of the organs except for bone marrow [6].

Biological context of Bromoethylene

• Inhalation carcinogenicity bioassay of vinyl bromide in rats [7].
• Due to the insufficiently low mutagenic activity in NER+ genotypes of vinyl bromide (VB), another epsilon-adduct-forming carcinogen, vermilion mutants could only be isolated from crosses of VB-treated males with NER- females [8].
• Twenty-two of 23 base substitutions induced in the vermilion gene after treatment of postmeiotic stages with vinyl carbamate or vinyl bromide fall into four categories of mutations expected from etheno bases: GC-->AT, AT-->GC, GC-->TA and AT-->TA base-pair changes [9].

Associations of Bromoethylene with other chemical compounds

• Vinyl bromide 125, representing the C6-C29 skeleton of caribenolide I (2), was prepared through the sequential alkylation of hydrazone 10 with bromide 116 and iodide 55, but failed to engage in the appropriate cross-coupling reaction with a variety of C1-C4 partners [10].

Gene context of Bromoethylene

• Vinyl bromide, which is a suspected carcinogen, is a minor product in lab studies, but so far there are no reports linking its presence with EDB in the field.(ABSTRACT TRUNCATED AT 400 WORDS)[11]

Analytical, diagnostic and therapeutic context of Bromoethylene

• The photodissociation dynamics of vinyl bromide and perfluorovinyl bromide have been investigated at 234 nm using a photofragment ion imaging technique coupled with a state-selective [2+1] resonance-enhanced multiphoton ionization scheme [12].

References