RESUMO
We report the formation and characterization of two diastereomeric thiol-ene addition products of the asthma medication Montelukast within chewing tablets. Widespread tin-based thermal stabilizers dioctyltin bis(2-ethylhexyl thioglycolate) and monooctyltin tris(2-ethylhexyl thioglycolate), used in the manufacturing process of the medication's forming foil, were identified as the source of the thiol reactant, showing that these stabilizers may play a part in the degradation of Montelukast and APIs with functionalities similar to those of Montelukast, which should be considered during development of medication. The isolation and analysis of these impurities was performed by HPLC and UV-vis spectroscopy. HRMS and NMR data were collected to characterize and determine the structures of these compounds.
Assuntos
Acetatos/uso terapêutico , Asma/tratamento farmacológico , Ciclopropanos/uso terapêutico , Compostos Orgânicos de Estanho/química , Quinolinas/uso terapêutico , Compostos de Sulfidrila/uso terapêutico , Sulfetos/uso terapêutico , Acetatos/análise , Ciclopropanos/análise , Humanos , Estrutura Molecular , Quinolinas/análise , Compostos de Sulfidrila/análise , Sulfetos/análise , TemperaturaRESUMO
The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.
Assuntos
Diterpenos/síntese química , Euphorbia/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ciclopentanos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Ésteres/química , Humanos , Estereoisomerismo , Especificidade por SubstratoRESUMO
[reaction: see text] A scalable enantioselective synthesis of the nonnatural 17-norjatrophane diterpene 3-propionyl-15-acetyl-17-norcharaciol is described. Key C/C-connecting transformations are an Evans aldol reaction, an intramolecular carbonyl ene reaction, a Horner-Wadsworth-Emmons olefination, and a ring-closing metathesis for the formation of a 12-membered carbacycle.
Assuntos
Alcenos/química , Diterpenos/síntese química , Diterpenos/química , Estrutura Molecular , EstereoisomerismoRESUMO
A convergent synthesis of the CDE and CDEF ring systems of pectenotoxin-2 from C and F ring precursors is described.