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  1. Home
  2. Browse by Author

Browsing by Author "Perez, Edwin G."

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    Fast and efficient synthesis of 2-(benzyloxy)-N,N-disubtituted-2-phenylethan-1-amines
    (2023) Rivero-Jerez, Paula S.; Saavedra-Olavarria, Jorge; Perez, Edwin G.
    A concise, metal catalyst free synthesis of 6-benzyloxyphenethylamines using the regioisomeric mixture obtained in the dialkylamine styrene oxide-ring opening products which reacted with MsCl to produce an aziridinium intermediate. This intermediate reacts, separately, with different benzyl alcohols to produce the desired products but using modern techniques such as fast heating in both steps.& COPY; 2023 Elsevier Ltd. All rights reserved.
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    Fast Heating-Assisted One-Pot Copper-Catalyzed Sulfonylation and Sulfochlorination of Styrenes
    (2022) Saavedra-Olavarria, Jorge; Hermosilla-Ibanez, Patricio; Almodovar, Iriux; Perez, Edwin G.
    Here, a strategy for the synthesis under fast-heating conditions of vinyl sulfones and beta-chlorosulfones from styrene derivatives, tosyl chloride (TsCl) as sulfonyl and chlorine source, and CuBr-neocuproine as the catalytic system is reported. The reaction occurs through an atom transfer radical addition (ATRA) mechanism to generate the sulfochlorinated adducts followed by E2 elimination to generate the vinyl sulfones. This methodology allows a wide range of vinyl sulfones and beta-chlorosulfones to be obtained using inexpensive reagents in one and five minutes respectively. These reactions appear as an interesting fast and easy-to-handle alternative to obtain these compounds.
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    PALLADIUM COMPLEX BEARING 3,5-BIS(BENZOTRIAZOL-1-YLMETHYL) TOLUENE LIGAND CATALYZES OXIDATIVE AMINATION OF ALLYL BUTYL ETHER
    (2013) Hurtado, John; Rojas, Rene S.; Perez, Edwin G.; Valderrama, Mauricio
    The reaction of 3,5-bis(bromomethyl)toluene with benzotriazole yields the bidentate ligand 3,5-bis(benzotriazol-1-ylmethyl)toluene (1). This ligand reacts with [PdCl2(cod)] (cod = 1,5-cyclooctadiene) to give the complex [PdCl2{3,5-bis(benzotriazol-1-ylmethyl)tolyl}] (2). These compounds were characterized by elemental analyses, mass spectra, and FTIR and NMR (H-1, C-13) spectroscopies. The palladium(II) complex 2 shows high activity as catalyst for oxidative amination, involving allyl butyl ether and phthalimide as substrates and PhICl2 as a stoichiometric oxidant.
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    Quinolin-2(1H-)-one-isoxazole dye as an acceptor for mild addition of bisulfite in cationic or zwitterionic aqueous micellar solutions
    (2024) Quintero, Guillermo E.; Espinoza, Catalina; Valencia, Jhesua; Insuasty, Daniel; Tiznado, William; Leiva-Parra, Luis; Santos, Jose G.; Perez, Edwin G.; Aliaga, Margarita E.
    (E)-6-Methoxy-1-methyl-3-(2-(3-methyl-4-nitroisoxazol-5-yl)vinyl)quinolin-2(1H)-one dye (MQI) has been synthesized, and its structural and electronic properties have been characterized by employing UV-vis spectroscopy in combination with computational methods. The MQI dye has been assessed as an activated Michael acceptor-type probe toward bisulfite ions. This reaction was kinetically tested in different mild, cationic (cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, and cetylpyridinium bromide), and zwitterionic (N-decyl-N,N-dimethyl-3-ammonio-1-propanesulfonate, N-tetradecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate, and N-hexacyl-N,N-dimethyl-3-ammonio-1-propanesulfonate) micellar solutions at pH similar to 5.5. Both micellar media remarkably allow the addition reactions, increasing the reactivity of MQI towards bisulfite ions, the biggest effects were found in the presence of cationic micelles. The binding constants of MQI with the micelles and the rate constants were determined from kinetic data, which were interpreted on the basis of the pseudophase kinetic model. The kinetic study and the product analysis allow us to highlight the relevant role of the association between MQI dye and the micellized surfactant, allowing efficient nucleophilic addition of bisulfite ions. The findings of this work will be valuable for the use of micellar solutions as an alternative medium to replace the use of toxic solvents to carry out organic reactions to perform nucleophilic addition reactions of bisulfite.
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    Side Groups Convert the α7 Nicotinic Receptor Agonist Ether Quinuclidine into a Type I Positive Allosteric Modulator
    (2023) Viscarra, Franco; Chrestia, Juan Facundo; Sanchez, Yaima; Perez, Edwin G.; Biggin, Philip C.; Bouzat, Cecilia; Bermudez, Isabel; Lopez, Jhon J.
    The quinuclidine scaffold has been extensively used forthe developmentof nicotinic acetylcholine receptor (nAChR) agonists, with hydrophobicsubstituents at position 3 of the quinuclidine framework providingselectivity for & alpha;7 nAChRs. In this study, six new ligands (4-9) containing a 3-(pyridin-3-yloxy)quinuclidinemoiety (ether quinuclidine) were synthesized to gain a better understandingof the structural-functional properties of ether quinuclidines.To evaluate the pharmacological activity of these ligands, two-electrodevoltage-clamp and single-channel recordings were performed. Only ligand 4 activated & alpha;7 nAChR. Ligands 5 and 7 had no effects on & alpha;7 nAChR, but ligands 6, 8, and 9 potentiated the currents evokedby ACh. Ligand 6 was the most potent and efficaciousof the potentiating ligands, with an estimated EC50 forpotentiation of 12.6 & PLUSMN; 3.32 & mu;M and a maximal potentiationof EC20 ACh responses of 850 & PLUSMN; 120%. Ligand 6 increased the maximal ACh responses without changing thekinetics of the current responses. At the single-channel level, thepotentiation exerted by ligand 6 was evidenced in thelow micromolar concentration range by the appearance of prolongedbursts of channel openings. Furthermore, computational studies revealedthe preference of ligand 6 for an intersubunit site inthe transmembrane domain and highlighted some putative key interactionsthat explain the different profiles of the synthesized ligands. Notably,Met276 in the 15 & PRIME; position of the transmembrane domain 2 almostabolished the effects of ligand 6 when mutated to Leu.We conclude that ligand 6 is a novel type I positiveallosteric modulator (PAM-I) of & alpha;7 nAChR.
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    Supramolecular Control of Reactivity toward Hydrolysis of 7-Diethylaminocoumarin Schiff Bases by Cucurbit[7]uril Encapsulation
    (2021) Alcazar, Jackson J.; Geue, Niklas; Valladares, Veronica; Canete, Alvaro; Perez, Edwin G.; Garcia-Rio, Luis; Santos, Jose G.; Aliaga, Margarita E.
    A series of aromatic Schiff bases, featuring 7-diethylamino-coumarin and with five different substituents at an adjacent phenyl ring, were synthesized and characterized. With the aim of assessing the stability of these dyes in acidic medium, their hydrolysis reactions were kinetically studied in the absence and presence of the macrocycle cucurbit[7]uril (CB[7]). Our results are consistent with a model containing three different forms of substrates (un-, mono-, and diprotonated) and three parallel reaction pathways. The pK(a) values and the rate constants were estimated and discussed in terms of the presence of a hydroxyl group at the ortho position and electron-releasing groups on the phenyl ring of the dyes. The kinetic study in the presence of CB[7] led to two different behaviors. Promotion of the reaction by CB[7] was observed for the hydrolysis of the Schiff bases containing only one coordination site toward the macrocycle. Conversely, an inhibitor effect was observed for the hydrolysis of a Schiff base with two coordination sites toward CB[7]. The latter effect could be explained with a model as a function of a prototropic tautomeric equilibrium and the formation of a 2:1 host/guest complex, which prevents the attack of water. Therefore, the kinetic results demonstrated a supramolecular control of the macrocycle toward the reactivity and stability of 7-diethylaminocoumarin Schiff bases in acidic medium.
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    Synthesis of N-Arylcytisine Derivatives Using the Copper-Catalyzed Chan-Lam Coupling
    (2021) Sanchez-Velasco, Oriel A.; Saavedra-Olavarria, Jorge; Araya-Santelices, Daniel A. A.; Hermosilla-Ibanez, Patricio; Cassels, Bruce K.; Perez, Edwin G.
    N-Arylcytisine derivatives are quite rare. We report here a practical methodology to obtain these compounds. Using the copper-catalyzed Chan-Lam coupling, we synthesized new N-arylcytisine derivatives at room temperature, in air and using inexpensive phenylboronic acids. Cytisine and 3,5-dihalocytisines can act as substrates, and among the products, the p-Br-derivative 2r was used as a substrate to obtain biaryl derivatives under Pd-coupling conditions; ester 2j was converted into its acid and amide derivatives using classical carbodiimide conditions. This shows that the Chan-Lam cross-coupling reaction can be included as a versatile synthetic tool in the derivatization of natural products.
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    Synthesis of N-arylsulfonamides via Chan-Lam Coupling Between Aryl Boronic Acids and N-[(sulfonyl)imino]phenyliodinanes
    (2021) Merchan-Arenas, Diego R.; Rivero-Jerez, Paula S.; Perez, Edwin G.
    We synthesized a library of 32 sulfonamides via CuBr2 catalyzed Chan-Lam C-N coupling, reaching excellent yields (until 81 %) under ligand-base-free, mild conditions, and short reaction times. A new non-toxic, versatile and easy to prepare starting materials, N-[(Sulfonyl)imino]phenyliodinanes were first time proposed as the nitrogen source in this synthetic tool. Finally, the sulfonamides were used as valuable building blocks in the synthesis of mono-alkyl anilines through their alkylation and Fukuyama deprotection steps.

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