Microwave-Assisted Convenient Syntheses of 2-Indolizine Derivatives from Morita-Baylis-Hillman Adducts: New in silico Potential Ion Channel Modulators
نویسندگان
چکیده
Neste artigo, um estudo sintético assistido por irradiação de micro-ondas para produzir 2-indolizina-carbonitrila e 2-indolizina-carboxilato de metila em bons a altos rendimentos (70 e 81%) em uma etapa a partir de adutos de Morita-Baylis-Hillman (AMBH) é apresentado. Estes compostos foram subsequentemente transformados em altos rendimentos (94-100%) em três derivados 2-indolizínicos. Os cinco compostos sintetizados foram idealizados in silico objetivando potenciais atividades seletivas como moduladores de canais iônicos. Estas atividades foram sugeridas pelos valores de pontuação usando o programa quimioinformático Molinspiration.
منابع مشابه
A convenient one-pot preparation of 2-methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman adducts and their oxidation to the corresponding sulfones.
A convenient one-pot preparation of 2-methyl-3-(phenylthiomethyl)quinolines from Morita-Baylis-Hillman adducts via conjugate addition of thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3-(phenylthiomethyl)quinolines were transformed into 2-methyl-3-(phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation.
متن کاملSynthesis of 16 New Hybrids from Tetrahydropyrans Derivatives and Morita-Baylis-Hillman Adducts: In Vitro Screening against Leishmania donovani.
Leishmaniases are a group of neglected tropical diseases (NTDs) caused by protozoan parasites from >20 Leishmania species. Visceral leishmaniasis (VL), also known as kala-aza, is the most severe form of leishmaniasis, usually fatal in the absence of treatment in 95% of cases. The Morita-Baylis-Hillman adducts (MBHAs) are being explored as drug candidates against several diseases, one of them be...
متن کاملA novel, tandem construction of C-N and C-C bonds: facile and one-pot transformation of the Baylis-Hillman adducts into 2-benzazepines.
A novel reaction involving tandem construction of C-N and C-C bonds via the simultaneous Ritter and Houben-Hoesch reactions on Baylis-Hillman adducts leading to a convenient, one-pot synthesis of 2-benzazepine derivatives is described. A facile stereoselective transformation of the Baylis-Hillman adducts into (E)- and (Z)-allyl amides is also presented.
متن کاملFirst example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives.
Treatment of pyridine-2-carboxaldehyde with activated alkenes such as alkyl vinyl ketones and cyclic enones in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a novel facile one-pot synthesis of indolizine derivatives, thus for the first time describing an electrophile induced Baylis-Hillman reaction.
متن کاملReactions of nitroxides XIII: Synthesis of the Morita–Baylis–Hillman adducts bearing a nitroxyl moiety using 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl as a starting compound, and DABCO and quinuclidine as catalysts
The Morita-Baylis-Hillman adducts bearing a nitroxyl moiety were synthesized from 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl and aliphatic, aryl and heterocyclic aldehydes.
متن کامل