Papers by Julio Alvarez-Builla
Arkivoc, Nov 25, 2006
The alkylation of sodium saccharin with alkyl halides to produce the intermediates ω-(1,1,3trioxo... more The alkylation of sodium saccharin with alkyl halides to produce the intermediates ω-(1,1,3trioxo-1,3-dihydrobenzo[d]isothiazol-2-yl)-alkanecarboxylic acids can be markedly improved by using microwave irradiation, both in terms of product yield and reaction time. While the process produces high yields with halo esters and halonitriles, the reaction with haloacids, which proceeds smoothly by conventional reflux, gives poorer yields with microwaves. This is due to an acid-base equilibrium produced by the rapid heating of the mixture under irradiation. Esters and nitriles can be converted into the acids by acid hydrolysis, without appreciable loss of the 1,1,3-trioxo-1,3-dihydrobenzo[d]isothiazole ring.
Bioorganic & Medicinal Chemistry, Aug 1, 2013
Several indole derivatives, that were highly potent ligands of GluN2B-subunit-containing N-methyl... more Several indole derivatives, that were highly potent ligands of GluN2B-subunit-containing N-methyl-Daspartate (NMDA) receptor, also demonstrated antioxidant properties in ABTS method. In particular, the 2-(4-benzylpiperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone (1) proved to be a dual-effective neuroprotective agent. With the aim to increase the antioxidant properties we added a catechol moiety onto piperidine moiety. The designed hybrid derivative 3,4-dihydroxy-N-[1-[2-(5-hydroxy-1H-indol-3yl)-2-oxoethyl]piperidin-4-yl]benzamide (10) was the most effective antioxidant agent (>94.1 ± 0.1% of inhibition at 17 lM) and showed GluN2B/NMDA receptor affinity at low micromolar concentration (IC 50 0.66 lM). By means of computational studies we explored the effect of the presence of this antioxidant fragment during the recognition process to binding pocket.
ChemInform, Feb 15, 2005
General experimental details. Melting points were uncorrected. Infrared spectra were recorded on ... more General experimental details. Melting points were uncorrected. Infrared spectra were recorded on NaCl pellets and spectral bands were reported in cm-1. 1 H NMR and 13 C NMR spectra were recorded at 200 / 300 MHz and 50 /75 MHz respectively. Chemical shifts were reported as δ values (ppm). The mass spectra (MS) were obtained as (ESI +). Ruthenium's catalyst 1 and 2, 2-vinylpyridine and alcohols were purchased from Aldrich. General procedure for the preparation of salts 4. A solution of the corresponding alcohol (2.6 mmol) and dry pyridine (0.205 g, 2.6 mmol) in dry CCl 4 (2 mL) was stirred at room temperature for 5-10 min under argon. Then the mixture was added dropwise (5-10 min) over a cooled solution (-10ºC) of triflic anhydride (0.733 g, 6 mmol) in dry CCl 4 (3 mL). The white solid formed was filtered off trough sodium sulphate, the solution was added via cannula to a solution of the vinyl derivative (2 mmol) in dry CCl 4 (2 mL) and the reaction mixture stirred for 24 h at room temperature. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (eluent: CH 2 Cl 2 /MeOH 9.5:0.5) or by washing with Et 2 O (4b, 4d, 4i and 4j).
ChemInform, Sep 1, 2010
www.cheminform.wiley-vch.de Protection O 0345 An Improved Method for the Synthesis of Allylic gem... more www.cheminform.wiley-vch.de Protection O 0345 An Improved Method for the Synthesis of Allylic gem-Diacetates from α,β-Unsaturated Aldehydes Catalyzed by Lithium Tetrafluoroborate.-(ONO, F.;
ChemInform, Jun 12, 2010
Use of the Stille Coupling Reaction on Heteroaromatic Cations: Synthesis of Substituted Quinolizi... more Use of the Stille Coupling Reaction on Heteroaromatic Cations: Synthesis of Substituted Quinolizinium Salts.-This is the first efficient application of Stille coupling reaction on heteroaromatic cations.The products are isolated as picrates after treatment of the crude bromides with sodium picrate in refluxing EtOH for 1h.-(BARCHIN, BERNARDO M.;
Advances in nitrogen heterocycles, 2000
Journal of Heterocyclic Chemistry, Jul 1, 1987
Industria farmacéutica: Equipos, procesos y tecnología, 1989
Investigative Ophthalmology & Visual Science, Mar 26, 2012
ChemInform, Jul 14, 2009
Efficient Functionalization of 2-Amino-6-chloropurine Derivatives at C-8 via 8-Lithiated Species.... more Efficient Functionalization of 2-Amino-6-chloropurine Derivatives at C-8 via 8-Lithiated Species.-The protection of the amino group in 2-amino-6-chloropurines using a THP group allows introduction of a variety of halogen and carbon substituents at the purine 8-position. Lithiation of non-protected chloropurine (XI) leads to a ring-opening of the pyrimidine ring to give (4-cyano-1H-imidazol-5-yl)cyanamide (XII).-(MAHAJAN,
PubMed, Nov 1, 1977
Crude analytical abscisic acid (ABA) exhibited fluorescence (lambdaex 340, lambdaem 425 nm). The ... more Crude analytical abscisic acid (ABA) exhibited fluorescence (lambdaex 340, lambdaem 425 nm). The results demonstrated a relationship between fluorescence response and ABA concentration, in the range of 0.04-0.38 microgram/ml. Chromatographic purification increased the emission signal, and oxidation induced by adding a sulphuric acid: ethanol (1:1) mixture also increased and displaced it (lambdaex 450, lambdaem 495 nm). Using these properties, a fluorimetric method for identification and evaluation of ABA, had been developed, and used for inhibitor recognition in P. pinea seed coats.
ChemInform, Aug 21, 2010
Synthesis of 1,4-Dihydropyridine Derivatives Containing Hydroxy-, Alkoxy-or Dimethylaminophenyl S... more Synthesis of 1,4-Dihydropyridine Derivatives Containing Hydroxy-, Alkoxy-or Dimethylaminophenyl Substituents at the 4-Position, Their Antioxidant Activity and Binding to Phospholipid Membranes.-A series of dihydropyridines of type (III) (21 examples) is synthesized by the Hantzsch method. Some 3,5-diamides and 4-(3',4'-dihydroxyphenyl) derivatives of (III) display antioxidant activity and an affinity to model phospholipid membranes.
ChemInform, Aug 23, 2010
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform, Aug 23, 2010
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
PubMed, Mar 1, 1997
A series of 1H-Imidazo and 1H-[1,2,3]-Triazolo fused derivatives have been obtained and tested as... more A series of 1H-Imidazo and 1H-[1,2,3]-Triazolo fused derivatives have been obtained and tested as non peptide AII receptor antagonists. Modification of the classical biphenyl moiety to a 4-arylthienyl fragment afforded interesting activities.
Wiley-VCH Verlag GmbH & Co. KGaA eBooks, Jul 27, 2011
ABSTRACT This chapter contains sections titled: Heterocyclic Compounds: An IntroductionStructure ... more ABSTRACT This chapter contains sections titled: Heterocyclic Compounds: An IntroductionStructure and Reactivity of Aromatic Five-Membered SystemsStructure and Reactivity of Aromatic Six-Membered SystemsBasic Literature on Heterocyclic CompoundsReferences
Tetrahedron, Apr 1, 2010
ABSTRACT
Tetrahedron, Mar 1, 2013
A study of Sonogashira copper-free coupling processes on pyridinium N-iodoheteroarylaminides has ... more A study of Sonogashira copper-free coupling processes on pyridinium N-iodoheteroarylaminides has been performed. A regioselective strategy starting from 3-bromo-5-substituted N-(pyridin-2-yl)pyridinium aminides and including N-alkylation, NeN bond reduction and a final Sonogashira reaction gave rise to a series of N-alkyl-3-alkynyl-5-arylpyridin-2-yl amines.
Organic Letters, Sep 17, 2003
Heteronucleophiles and C-nucleophiles chemoselectively react with N-acyl (S)-ethyl 4,4-dimethyl p... more Heteronucleophiles and C-nucleophiles chemoselectively react with N-acyl (S)-ethyl 4,4-dimethyl pyroglutamate (DMPG) affording esters, amides, and ketones in high yield. The intramolecular process allows the stereoselective formation of-hydroxy acids likely by formation and ring opening of the corresponding-lactones
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Papers by Julio Alvarez-Builla