Paper
A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.
Published Jun 15, 2009 · G. Kraus, Haitao Guo
The Journal of organic chemistry
Q2 SJR score
16
Citations
0
Influential Citations
Abstract
The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or alpha,beta-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4-dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.
Study Snapshot
This study presents a flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts, leading to the direct synthesis of rutaecarpine in high yields.
PopulationOlder adults (50-71 years)
Sample size24
MethodsObservational
OutcomesBody Mass Index projections
ResultsSocial networks mitigate obesity in older groups.
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References
RETRACTED: Rutaecarpine inhibits hypoxia/reoxygenation-induced apoptosis in rat hippocampal neurons
This paper has been retracted due to a significant error in the preparation of the paper and manipulation of images.
2008·19citations·Zhong Dai et al.·Neuropharmacology
Neuropharmacology
Lynamicins A-E, chlorinated bisindole pyrrole antibiotics from a novel marine actinomycete.
Lynamicins A-E, found in a novel marine actinomycete, possess broad-spectrum antimicrobial activity against both Gram-positive and Gram-negative organisms, including drug-resistant pathogens.
2008·144citations·K. McArthur et al.·Journal of natural products
Journal of natural products
Calcitonin gene-related peptide-mediated antihypertensive and anti-platelet effects by rutaecarpine in spontaneously hypertensive rats
Rutaecarpine (Rut) exerts both antihypertensive and anti-platelet effects in spontaneously hypertensive rats by stimulating CGRP synthesis and release, with its anti-platelet effect related to inhibiting platelet-derived tissue factor release.
2008·39citations·Dai Li et al.·Peptides
Peptides
Synthesis of hybrids between the alkaloids rutaecarpine and luotonins A, B
The synthesized compounds show cytotoxic activities against HeLa cells and apoptosis inducing effects at a concentration comparable to etoposide, indicating potential as cancer treatments.
2008·24citations·Máté Bubenyák et al.·Tetrahedron Letters
Tetrahedron Letters
One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A.
This one-pot reaction enables the synthesis of 2-substituted indoles in high yields (81-97%), which can be used as an intermediate in the synthesis of arcyriacyanin A.
2008·50citations·G. Kraus et al.·Organic letters
Organic letters
Antifouling activity of a dibrominated cyclopeptide from the marine sponge Geodia barretti.
Bromobenzisoxazolone barettin, a novel dibrominated cyclopeptide from the marine sponge Geodia barretti, effectively inhibits barnacle larvae settlement with an EC 50 value of 15 nM.
2008·52citations·E. Hedner et al.·Journal of natural products
Journal of natural products
One-pot reductive-cyclization as key step for the synthesis of rutaecarpine alkaloids
A one-pot reductive-cyclization reaction efficiently synthesizes rutaecarpine alkaloids from a key intermediate, enabling the production of euxylophoricine A, B, and C.
2008·12citations·C. Lee et al.·Tetrahedron Letters
Tetrahedron Letters
Synthesis, spectral behaviour and biological activity of benzoxazonyl(quinoxalonyl)-benzfurano-(indolo)-quinoline apocyanine dyes
The new cyanines show promising bactericidal and fungicidal activity against various bacterial and fungal strains.
2007·7citations·Z. H. Khalil et al.·Journal of Chemical Technology & Biotechnology
Journal of Chemical Technology & Biotechnology
Citations
Palladium-catalyzed synthesis of 2-alkenyl-3-arylindoles via a dual α-arylation strategy: formal synthesis of the antilipemic drug fluvastatin.
Palladium-catalyzed dual -arylation of TES-enol ethers of enones provides a highly efficient and selective method for synthesising substituted 2-alkenyl-3-arylindoles, leading to the cholesterol-lowering drug fluvastatin.
2015·9citations·A. P. Kale et al.·Organic & biomolecular chemistry
Organic & biomolecular chemistry
Rhodium-Catalyzed C-H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substituted Indoles.
Rhodium-catalyzed C-H annulation of nitrones with symmetrical diaryl alkynes provides a regioselective route to prepare 2,3-diaryl-substituted N-unprotected indoles with two different aryl groups
2015·100citations·Hao Yan et al.·Angewandte Chemie
Angewandte Chemie
Investigating the molecular and aggregated states of a drug molecule rutaecarpine using spectroscopy, microscopy, crystallography and computational studies.
Rutaecarpine's photophysical properties can be influenced by surface active ionic liquids, which can dissociate colloidal aggregates and encapsulate molecular species, potentially influencing drug activity.
2015·24citations·Shiba S Dandpat et al.·Physical chemistry chemical physics : PCCP
Physical chemistry chemical physics : PCCP
Fused perylene-phthalocyanine macrocycles: a new family of NIR-dyes with pronounced basicity.
PePc macrocycles, a new family of NIR-dyes with pronounced basicity, show transparency in the visible region but light absorption in the NIR region.
2014·6citations·Jörg Schönamsgruber et al.·Chemistry
Chemistry
Regioselectivity of Larock heteroannulation: a contribution from electronic properties of diarylacetylenes.
Larock heteroannulation leads to regioselectivity in the synthesis of 2,3-diarylindoles, with electron-withdrawing substituents yielding 2,3-diarylindoles and electron-donating groups yielding indole products.
2013·23citations·Nared Phetrak et al.·The Journal of organic chemistry
The Journal of organic chemistry
Synthesis of indole analogues of the natural schweinfurthins.
This study presents a facile approach for synthesis of new heteroaromatic analogues of natural schweinfurthins, providing facile access to antiproliferative natural stilbenes.
2013·18citations·J. Kodet et al.·The Journal of organic chemistry
The Journal of organic chemistry
Aryne insertion reactions leading to bioactive fused quinazolinones: diastereoselective total synthesis of cruciferane.
Aryne insertion reactions enable efficient, one-step synthesis of bioactive natural products like tryptanthrin, phaitanthrins A-C, and cruciferane.
2013·62citations·Sagar D. Vaidya et al.·Organic letters
Organic letters