Gattermann reaction of 3,5-dimethoxyphenylacetonitrile. Synthesis of 6,8-dioxyisoquinolines

White, James D.; Straus, D. S.

doi:10.1021/jo01284a009

Cited by 8 publications

(3 citation statements)

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Section: Resultssupporting

confidence: 79%

“…The 13 C NMR spectrum (Table 2) showed 10 carbon signals including one methoxy, five aromatic methines, and four aromatic non-protonated carbons. These NMR data were similar to those of 6,8-dimethoxyisoquinolin [15] and papraline [16], and the only clear difference between 1 and 6,8-dimethoxyisoquinolin was the disappearance of one oxygenated methyl, which indicated that 1 was also an isoquinoline alkaloid. This was supported by the HMBC spectrum showing correlations from H-1 to C-3/C-4a/C-8a, H-3 to C-4/C-4a, H-4 to C-3/C-5/C-8a, H-5 to C-4/C-6/C-7/C-8a, and H-7 to C-5/C-6/C-8/C-8a.…”

Section: Resultssupporting

confidence: 72%

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Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus Aspergillus puniceus

Liu

Yao

Lu³

et al. 2022

Marine Drugs

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Puniceusines A–N (1–14), 14 new isoquinoline alkaloids, were isolated from the extracts of a deep-sea-derived fungus, Aspergillus puniceus SCSIO z021. Their structures were elucidated by spectroscopic analyses. The absolute configuration of 9 was determined by ECD calculations, and the structures of 6 and 12 were further confirmed by a single-crystal X-ray diffraction analysis. Compounds 3–5 and 8–13 unprecedentedly contained an isoquinolinyl, a polysubstituted benzyl or a pyronyl at position C-7 of isoquinoline nucleus. Compounds 3 and 4 showed selective inhibitory activity against protein tyrosine phosphatase CD45 with IC50 values of 8.4 and 5.6 µM, respectively, 4 also had a moderate cytotoxicity towards human lung adenocarcinoma cell line H1975 with an IC50 value of 11.0 µM, and 14, which contained an active center, -C=N+, exhibited antibacterial activity. An analysis of the relationship between the structures, enzyme inhibitory activity and cytotoxicity of 1–14 revealed that the substituents at C-7 of the isoquinoline nucleus could greatly affect their bioactivity.

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Section: Resultssupporting

confidence: 79%

Section: Resultssupporting

confidence: 72%

Isoquinoline Alkaloids as Protein Tyrosine Phosphatase Inhibitors from a Deep-Sea-Derived Fungus Aspergillus puniceus

Liu

Yao

Lu³

et al. 2022

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…15 In the reaction of 3,5-dimethoxyphenylacetonitrile using zinc cyanide and either Hydrogen Bromide or hydrogen chloride (eq 7), 15 N-labeling showed that the nitrogen in the product came from the zinc cyanide. 16 It is noteworthy that two activating substituents are required; an attempted reaction was unsuccessful using 3,4-dimethoxyphenylacetonitrile. β-Oxoaldimines are formed when ketones such as deoxybenzoin are reacted under Gattermann conditions.…”

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confidence: 99%