Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity

A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, and the derivative (±)-11-methoxy-5,6,6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1,2-a]naphthalene-12-ol from the...

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Published inJournal of the Brazilian Chemical Society Vol. 29; no. 12; pp. 2646 - 2656
Main Authors Diaz-Muñoz, Gaspar, Miranda, Izabel, Sartori, Suélen, Dias, Gabriel, Kohlhoff, Markus, Purgato, Gislaine, Diaz, Marisa
Format Journal Article
LanguageEnglish
Published Sociedade Brasileira de Química 01.12.2018
Subjects
CHEMISTRY, MULTIDISCIPLINARY
Wittig reaction
antibacterial activity
tetrahydroquinoline alkaloids
solvolytic N-methylation
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Abstract A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, and the derivative (±)-11-methoxy-5,6,6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1,2-a]naphthalene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt0, generated in situ by reduction of PtO2. The evaluation of biofilm inhibition and antibacterial activity of the compounds against Staphylococcus aureus strains isolated from cows with mastitis revealed that the alkaloid derivative is a promising candidate for an antibiotic drug.
AbstractList A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, and the derivative (±)-11-methoxy-5,6,6a,7,8,13-hexahydro-13a-aza-benzo[5,6]cyclohepta [1,2-a]naphthalene-12-ol from their respective Wittig adducts in moderate and high yields. The solvolytic N-methylation reaction was shown to be catalyzed by Pt0, generated in situ by reduction of PtO2. The evaluation of biofilm inhibition and antibacterial activity of the compounds against Staphylococcus aureus strains isolated from cows with mastitis revealed that the alkaloid derivative is a promising candidate for an antibiotic drug.
Author Diaz, Marisa
Sartori, Suélen
Kohlhoff, Markus
Diaz-Muñoz, Gaspar
Dias, Gabriel
Purgato, Gislaine
Miranda, Izabel
AuthorAffiliation Universidade Federal de Viçosa
Fundação Oswaldo Cruz
Universidade Federal de Minas Gerais
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  givenname: Marisa
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  fullname: Diaz, Marisa
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Issue 12
Keywords Wittig reaction
antibacterial activity
tetrahydroquinoline alkaloids
solvolytic N-methylation
Language English
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  publication-title: Bioorg. Med. Chem. Lett.
  contributor:
    fullname: Scott, J. D.; Miller, M. W.; Li, S. W.; Lin, S.-I.; Vaccaro, H. A.; Hong, L.; Mullins, D. E.; Guzzi, M.; Weinstein, J.; Hodgson, R. A.; Varty, G. B.; Stampord, A. W.; Chan, T.-Y.; McKittrick, B. A.; Greenlee, W. J.; Priestley, T.; Parker, E. M.
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Snippet A novel one-pot sequence (in 2 or 3 steps) was developed for the synthesis of the tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine...
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StartPage 2646
SubjectTerms CHEMISTRY, MULTIDISCIPLINARY
Title Unprecedented One-Pot Sequence for the Synthesis of Tetrahydroquinoline Alkaloids and Preliminary Evaluation of their Antibacterial Activity
URI http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018001202646&lng=en&tlng=en
Volume 29
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