Safety of Ethyl 3-bromo-2-oxopropanoate. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Ethyl 3-bromo-2-oxopropanoate, is researched, Molecular C5H7BrO3, CAS is 70-23-5, about Synthesis of the deacetoxytubuvaline fragment of pretubulysin and its lipophilic analogs for enhanced permeability in cancer cell lines. Author is Reddy, Ramesh B.; Dudhe, Premansh; Chelvam, Venkatesh.
In the last two decades, tubulysins have emerged as alternatives to microtubule depolymerizing agents such as colchicine and vinblastine, which are well-established anticancer agents. However, the complex structure of tubulysins has always posed a challenge for synthetic chemists to scale up the production of these compounds We report a new strategy for the practical gram-scale synthesis of a (4R)-4-[( tert-butoxycarbonyl)amino]-5-methylhexanoic acid through regioselective cleavage of a chiral aziridine ring with a vinyl Grignard reagent to afford tert-Bu [(1R)-1-isopropylbut-3-en-1-yl]carbamate, which was subjected to regioselective hydroboration-oxidation with 9-BBN. The resulting (4R)-4-[( tert-butoxycarbonyl)amino]-5-methylhexanoic acid was successfully transformed into the deacetoxytubuvaline fragment of pretubulysin or its highly lipophilic methyl-substituted thiazole and oxazole analogs for incorporation into pretubulysins. Increasing the lipophilicity of tubulysin or pretubulysin mols. should enhance their cell permeability and cytotoxicity in cancer cell lines.
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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem