The nitration of some 4,6-dimethoxyindoles

Jones, Ashley; Purwono, Bambang; Bowyer, Paul K.; Mitchell, Peter S. R.; Kumar, Naresh; Nugent, Stephen J.; Jolliffe, Katrina A.; Black, David StC.

doi:10.1016/j.tet.2004.08.086

Cited by 17 publications

(4 citation statements)

References 20 publications

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“…T(MQ)EN and T(TMQ)EN were synthesized from ethylenediamine and 4 equiv of (halomethyl)quinolines (Scheme ). 2-(Bromomethyl)-6-methoxyquinoline ( 2 ) was obtained from 6-methoxyquinaldine ( 1 ) using NBS; however, bromination of 5,6,7-trimethoxyquinaldine ( 3 ) under similar reaction condition was unsuccessful. Thus, 2-(chloromethyl)-5,6,7-trimethoxyquinoline ( 6 ) was prepared in three steps as shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

Methoxy-Substituted TQEN Family of Fluorescent Zinc Sensors

et al. 2006

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Two methoxy-substituted TQEN (N,N,N',N'-tetrakis(2-quinolylmethyl)ethylenediamine) derivatives, T(MQ)EN (N,N,N',N'-tetrakis(6-methoxy-2-quinolylmethyl)ethylenediamine) and T(TMQ)EN (N,N,N',N'-tetrakis(5,6,7-trimethoxy-2-quinolylmethyl)ethylenediamine), have been prepared, and their fluorescence properties with respect to Zn2+ coordination were investigated. Introduction of a methoxy substituent at 6-position of the quinoline ring enhances the fluorescence intensity by 10-fold, and the three methoxy substituents in the 5,6,7-positions afford significant enhancement of the long-wavelength component of the fluorescence of zinc complex. The substituents did not alter the binding affinity of these compounds toward zinc ion significantly. T(MQ)EN was proved to be effective in detection of zinc ion in cells by fluorescent microscopy.

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Section: Resultsmentioning

confidence: 99%

Methoxy-Substituted TQEN Family of Fluorescent Zinc Sensors

et al. 2006

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“…Installation of the critical acetic acid side chain was then accomplished through acylation of the electron rich indole ring system with oxalyl chloride followed by the addition of methanol to give ester 3 . 21 Selective reduction of the ketone with sodium borohydride cleanly provided alcohol 4 . Alkylation using the resin bound acid, Amberlyst 15, successfully generated the desired t -butyl ether, although other conditions established for the introduction of the t -butyl ether functionality including the use of either t -BuOAc/perchloric acid or t -butylacetimidate have also been successfully applied to the indole system.…”

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confidence: 99%

Indole-based allosteric inhibitors of HIV-1 integrase

Patel

Kvaratskhelia

Mansour

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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Employing a scaffold hopping approach, a series of allosteric HIV-1 integrase (IN) inhibitors (ALLINIs) have been synthesized based on an indole scaffold. These compounds incorporate the key elements utilized in quinoline-based ALLINIs for binding to the IN dimer interface at the principal LEDGF/p75 binding pocket. The most potent of these compounds displayed good activity in the LEDGF/p75 dependent integration assay (IC50 = 4.5 μM) and, as predicted based on the geometry of the five-versus six-membered ring, retained activity against the A128T IN mutant that confers resistance to many quinoline-based ALLINIs.

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“…However, it seems that the pure Si-MCM-41 shows a slightly higher catalytic activity than the blank; perhaps, the weak acidity of MCM-41 or the enhanced acidity of adsorbed nitric acid molecules induced by MCM-41 become involved in this catalytic process in some way [20].…”

Section: Nitration Of Toluene With Different Catalystsmentioning

confidence: 99%