39856-58-1Relevant articles and documents
A High-Throughput Assay for Arylamine Halogenation Based on a Peroxidase-Mediated Quinone-Amine Coupling with Applications in the Screening of Enzymatic Halogenations
Hosford, Joseph,Shepherd, Sarah A.,Micklefield, Jason,Wong, Lu Shin
supporting information, p. 16759 - 16763 (2016/02/12)
Arylhalides are important building blocks in many fine chemicals, pharmaceuticals and agrochemicals, and there has been increasing interest in the development of more "green" halogenation methods based on enzyme catalysis. However, the screening and development of new enzymes for biohalogenation has been hampered by a lack of high-throughput screening methods. Described herein is the development of a colorimetric assay for detecting both chemical and enzymatic arylamine halogenation reactions in an aqueous environment. The assay is based on the unique UV/Vis spectrum created by the formation of an ortho-benzoquinone-amine adduct, which is produced by the peroxidase-catalysed benzoquinone generation, followed by Michael addition of either a halogenated or non-halogenated arylamine. This assay is sensitive, rapid and amenable to high-throughput screening platforms. We have also shown this assay to be easily coupled to a flavin-dependent halogenase, which currently lacks any convenient colorimetric assay, in a "one-pot" workflow.
NOVEL ANTIMALARIA AGENT CONTAINING HETEROCYCLIC COMPOUND
-
Page/Page column 63, (2008/06/13)
Disclosed is an antimalarial agent containing a compound represented by the formula: [wherein A1 represents a 3-pyridyl group that may have a substituent, a 6-quinolyl group that may have a substituent, or the like; X1 represents a group represented by the formula -C(=O)-NH- or the like; E represents a furyl group, a thienyl group or a phenyl group; with the proviso that A1 may have one to three substituents, and E has one of two substituents] or a salt thereof or hydrates thereof.
NOVEL ANTIFUNGAL AGENT COMPRISING HETEROCYCLIC COMPOUND
-
Page/Page column 71, (2010/11/08)
The present invention provides an antifungal agent represented by the formula: [wherein A1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X1 represents a group represented by the formula -NH-C(=O)-, a group represented by the formula -C(=O)-NH-, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A1 may have 1 to 3 substituents, and E has one or two substituents].
SUBSTITUTED AZACHINAZOLINES HAVING AN ANTIVIRAL ACTION
-
Page/Page column 22, (2008/06/13)
The invention relates to substituted azachinazolines and methods for the production thereof. The invention also relates to the use of said azachinazolines for producing medicaments for the treatment and/or prophylaxis of diseases, especially for using as antiviral agents, especially against cytomegaloviruses.
Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands
-
, (2008/06/13)
The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of disorders relating to or affected by the 5-HT6 receptor.
Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters
Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valerie,Bovy, Philippe R.,Rault, Sylvain
, p. 3323 - 3328 (2007/10/03)
This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen-metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pb-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.
Mild regioselective halogenation of activated pyridines with N-bromosuccinimide
Canibano,Rodriguez,Santos,Sanz-Tejedor,Carreno,Gonzalez,Garcia-Ruano
, p. 2175 - 2179 (2007/10/03)
Regioselective mono and dihalogenations of amino, hydroxy and methoxy pyridines (2-, 3-, and 4-substituted) as well as 2,6-dimethoxy pyridine with N-bromosuccinimide in different solvents have been studied. Reactivity of the substrates decreases in the order amino>hydroxy>methoxy and regioselectivity depends on the position of the substituent (2-substituted > 3-substituted). In most of the cases we obtained monobrominated derivatives regioselectively and in high yields. Hydroxy and amino pyridines can also be dibrominated in almost quantitative yield with 2 equivalents of NBS.
The ortho effect in pyridines. Part XI(1). Substituent effects on basicity of 2- and 4-substituted 3-aminopyridines
Rasala, D.
, p. 79 - 84 (2007/10/02)
The substituent effects on the pKa values corresponding to the first protonation site of thirty 2- and 4-substituted 3-aminopyridines have been studied.It was found that the relative localized and delocalized effects are apparently sensitive to the variation of substituent position in the pyridine ring.An interaction of the 2-substituent with the protonation centre has mainly inductive character, whereas, the pKa values of 4-substituted 3-aminopyridines are highly affected by through-resonance.The steric effect was found to be insignificant.Keywords: substituent effects / 2- and 4-substituted 3-aminopyridines / basicity
REVIEW ON THE METALLATION OF ?-DEFICIENT HETEROAROMATIC COMPOUNDS; REGIOSELECTIVE ORTHO-LITHIATION OF 3-FLUOROPYRIDINE: DIRECTING EFFECTS AND APPLICATION TO SYNTHESIS OF 2,3- OR 3,4-DISUBSTITUTED PYRIDINES
Marsais, Francis,Queguiner, Guy
, p. 2009 - 2021 (2007/10/02)
Metallation of ?-deficient heterocyclic compounds is first reviewed, which shows the important recent developments in this research area.A particular aspect of this reaction is then given with the study of the 3-fluoropyridine metallation regioselectivity.Lithiation of 3-fluoropyridine is chemoselective at low temperatures using butyllithium-polyamine chelates or lithium diisopropylamide.Protophilic attack by these strong bases can be directed either at the 2- or 4-position depending on the lithiation conditions.Various reaction parameters are thus studied such as solvent, temperature, reaction time, lithium-chelating agent as well as metallating agent.The high regioselectivity of 3-fluoropyridine lithiation is theoretically discused, in particular in terms of kinetic of thermodynamic control of the metallation.Chelation between butyllithium and 3-fluoropyridine is proposed, which completely modifies the heterocycle reactivity toward the lithiating agent.This is confirmed by theoretical quantum calculations performed on different models of 3-fluoropyridine using the CNDO/2.These results allow to select the best 3-fluoropyridine-metallation conditions which lead to 3-fluoro-2-lithiopyridine on the one hand and to 3-fluoro-4-lithiopyridine on the other hand.Each of the lithiated isomers is then reacted with a great variety of electrophiles which gives very conveniently the corresponding 2,3- or 3,4-disubstituted pyridines.
