In 2014,Gaugaz, Fabienne Z.; Redondo-Horcajo, Mariano; Barasoain, Isabel; Diaz, J. Fernando; Cobos-Correa, Amanda; Kaufmann, Markus; Altmann, Karl-Heinz published 《The Impact of Cyclopropane Configuration on the Biological Activity of Cyclopropyl-Epothilones》.ChemMedChem published the findings.SDS of cas: 329-59-9 The information in the text is summarized as follows:
Two cis-12,13-cyclopropyl-epothilone B variants have been synthesized, differing only in the configuration of the stereocenters at C12 and C13. The syntheses were based on a common allylic alc. intermediate that was converted into the corresponding diastereomeric hydroxymethyl-cyclopropanes by means of a stereoselective Charette cyclopropanation. A macrocyclization were accomplished through ring-closing metathesis (RCM). Substantial differences between the two compounds were found with regard to microtubule binding affinity, antiproliferative activity and their effects on the cellular microtubule network. While the analog with the cyclopropane group oriented in a corresponding way to the epoxide configuration in natural epothilones was almost equipotent with epothilone A the other was significantly less active. Based on these findings, natural epothilone-like activity of cis-fused 12,13-cyclopropyl-epothilone analogs is tightly linked to the natural orientation of the cyclopropane moiety. The synthesis of the target compounds was achieved using (3S,6R,7S,8S)-3,7-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,6,8-tetramethyl-5-oxo-9-decenoic acid as a starting material. The title compounds thus formed included (benzimidazolyl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione diastereomers (epothilone analogs).Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9SDS of cas: 329-59-9) was used in this study.
Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.SDS of cas: 329-59-9Methyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics