The nitration of some methyl substituted indole-3-aldehydes in sulphuric acid

Settimo, A. Da; Saettone, M. F.

doi:10.1016/s0040-4020(01)98332-2

Cited by 18 publications

(2 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fractions containing 5a were collected and submitted to a further chromatography (silica gel, CH 2 Cl 2 −hexane, 6:4, as eluent) for the elimination of formed methyl N- methyl-4-nitroanthranilate: yield 7.83 g (57%), orange crystals; mp 156 °C (lit. 156−157 °C); 1 H NMR (200 MHz, CDCl 3 ) δ 8.01 (d, 1H, J = 8.8, H-6), 7.51 (d, 1H, J = 2.2, H-3), 7.41 (dd, 1H, J = 8.8, 2.2, H-5), 6.07 (br, s, 2H, N H 2 ), 3.93 (s, 3H, C H 3 ); MS (EI) m / z 196 [M + ]. Anal.…”

Section: Methodsmentioning

confidence: 99%

Evaluation and Biological Properties of Reactive Ligands for the Mapping of the Glycine Site on theN-Methyl-d-aspartate (NMDA) Receptor

et al. 1999

View full text Add to dashboard Cite

The glycine-binding site of the N-methyl-D-aspartate (NMDA) receptor, given its potential as pharmacological target, has been thoroughly studied by structure-activity relationships, which has made possible its description in terms of spatial limits and interactions of various types. A structural model, based on mutational analysis and sequence alignements, has been proposed. Yet, the amino acid residues responsible for the interactions with the ligand have not been unambiguously characterized. To evidence nucleophilic pocket-lining residues, we have designed and synthesized reactive glycine-site ligands derived from 3-substituted 4-hydroxy-quinolin-2(1H)-ones by introducing various electrophilic groups at different positions of the molecule. These ligands were found to have high affinity at the glycine site and to be functional antagonists by inhibiting glycine/glutamate-induced currents in transfected oocytes. The correlation between their potency and their substitution pattern was strictly consistent with previously established structure-activity relationships. Most ligands displayed intrinsic reactivity toward cysteine, but none inactivated wild-type receptors. This is consistent with the model since it indicates the absence of exposed cysteine in the glycine-binding site. A strategy of cysteine incorporation by point mutations at selected polypeptide positions will create unambiguously localized targets for our reactive probes.

show abstract

Section: Methodsmentioning

confidence: 99%

Evaluation and Biological Properties of Reactive Ligands for the Mapping of the Glycine Site on theN-Methyl-d-aspartate (NMDA) Receptor

et al. 1999

View full text Add to dashboard Cite

show abstract

“…During the synthesis of Indole-3-aldehyde, James and Snyder observed that that the most reactive position on indole for electrophilic aromatic substitution is C-3, which is 10 13 times more reactive than benzene [43]. However, a noteworthy exception took place when Noland, Smith, and Rush, carried out nitration of 2-Phenylindole under acidic conditions [44][45][46][47][48][49][50][51][52]. Electrophilic nitration took place at C-5 (carbocyclic ring), because C-3 of pyrrole ring is protonated.…”

Section: Product Analysis Under Kinetic Conditionsmentioning

confidence: 99%

Trichloroisocyanuric acid and NaNO2 mediated nitration of indoles under acid-free and Vilsmeier–Haack conditions: synthesis and kinetic study

et al. 2019

View full text Add to dashboard Cite

This study deals with the synthetic and kinetic aspects of trichloroisocyanuric acid (TCCA) and NaNO 2 mediated nitration of indoles in aqueous acetonitrile media under acid-free and Vilsmeier-Haack conditions (using N,N′-dimethyl amides) conditions. Nitration of indoles revealed second order kinetics, with a first order dependence on [indole] and [nitrating agent] ([TCCA]/[NaNO 2 ], [(TCCA-DMF)]/[NaNO 2 ] or [(TCCA-DMA)]/[NaNO 2 ], in which [NaNO 2 ] far excess over other reagents). Reactions followed overall second order kinetics with first order in [reagent] and [indole] under the experimental conditions. Isokinetic temperature (β) values were obtained from Leffler's equation for different kinetic protocols (β = 303 K (TCCA-NaNO 2 ); 303 K (TCCA-DMF)/NaNO 2 ; and 244 K (TCCA-DMA)/NaNO 2 ). These values are the experimental temperature range (303-323 K) indicating that the entropy factors are probably more important in controlling the reaction.

show abstract

The reaction of some indoles with acetic‐formic anhydride

Bergman

1971

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The nitration of some methyl substituted indole-3-aldehydes in sulphuric acid

Cited by 18 publications

References 6 publications

Evaluation and Biological Properties of Reactive Ligands for the Mapping of the Glycine Site on theN-Methyl-d-aspartate (NMDA) Receptor

Evaluation and Biological Properties of Reactive Ligands for the Mapping of the Glycine Site on theN-Methyl-d-aspartate (NMDA) Receptor

Trichloroisocyanuric acid and NaNO2 mediated nitration of indoles under acid-free and Vilsmeier–Haack conditions: synthesis and kinetic study

The reaction of some indoles with acetic‐formic anhydride

Contact Info

Product

Resources

About