Síntesis de un precursor quiral de rotaxano bifuncional

La nanotecnología es una ciencia actual que se basa en la manipulación y el desarrollo de la materia, pero en uno de los niveles más pequeños que no nos podemos imaginar, los niveles nanométricos. Uno de los principales ejemplos son los rotaxanos, los cuales son moléculas diminutas en forma de mancuernas capaz de actuar como un interruptor molecular, es decir una molécula que es capaz de activar y desactivar componentes moleculares y en consecuencia iniciar o frenar algún efecto; está formado por un eje y un macrociclo alrededor de este. En el presente trabajo se muestra la síntesis de un eje quiral molecular a partir de dos moléculas biológicamente importantes la primera derivada de un carbohidrato (α-Dglucofuranosa) y la otra un aminoácido (L-prolina) las cuales están unidas a través de dos 1,2,3 triazoles los cuales se sintetizaron mediante química click CuAAC empleando como catalizador CuI.Nanotechnology is a current science that is based on the manipulation and development of matter, but at one of the smallest levels that we can imagine, the nanometric levels. One of the main examples are the rotaxanes, which are tiny dumbbell-shaped molecules capable of acting as a molecular switch, i.e., a molecule that is able to activate and deactivate molecular components and consequently start or stop some effect and is formed by a chiral axis and a macrocycle around it. In the present work we show the synthesis of a molecular axis from two biologically important molecules, the first derived from a carbohydrate (α-D-glucofuranose) and the other from an amino acid (L-proline) which are linked through two 1,2,3 triazoles which were synthesized by CuAAC click chemistry using CuI as catalyst

Preparación de un plausible eje de rotaxano quiral aminoácido-esteroide

Rotaxanes are compounds that are made up of two submolecular components: a cyclic one (a ring) and a linear one (an axis) that threads the previous one and that, in addition, has bulky groups at their ends in order to keep both components intertwined. Another simple tool to keep this type of macrostructures anchored is through non-covalent bonds such as hydrogen bonds, coordination bonds with metal ions and aromatic π-π interactions, among others. In this work the rapid and quantitative synthesis of a conductive thread (chiral axis) composed of chiral molecules is reported, which give it excellent anchoring properties important for the synthesis of rotaxanes.Rotaxanes are compounds that are made up of two submolecular components: a cyclic one (a ring) and a linear one (an axis) that threads the previous one and that, in addition, has bulky groups at their ends in order to keep both components intertwined. Another simple tool to keep this type of macrostructures anchored is through non-covalent bonds such as hydrogen bonds, coordination bonds with metal ions and aromatic π-π interactions, among others. In this work the rapid and quantitative synthesis of a conductive thread (chiral axis) composed of chiral molecules is reported, which give it excellent anchoring properties important for the synthesis of rotaxanes

Síntesis de etinil estradiol y su aplicación en una reacción de ciclo adición catalizada por Cu(I)

El etinilestradiol es un esteroide común en medicamentos de terapia y regulación hormonal y contiene en su estructura un grupo alquino en el carbono 17 que permite llevar a cabo una reacción de ciclo adición [3+2] para la obtención de 1, 2, 3 triazoles. En este trabajo se describe una metodología alternativa para la obtención del etinilestradiol a partir de estrona mediante una reacción de Grignard empleando como nucleófilo al bromuro de etilinilmagnesio, este derivado se utilizó como sintón para la formación de un triazol hibrido compuesto de un esteroide y un azida derivada de carbohidrato (3-azida-1,2:5,6-diisopropiliden--D-glucofuranosa) bajo condiciones de térmicas clásicas. Los productos de reacción fueron caracterizados mediante espectroscopia de infrarrojo y resonancia magnética nuclear hidrogeno y carbono 13.Ethinylestradiol is a common steroid in therapy and hormone regulation drugs and contains in its structure an alky negro up at carbon 17th at allows to carry out a[3+2] cycloaddition reaction to obtain 1, 2, 3 triazoles. In this work we describe an alternative methodology to obtain ethinylestradiol from estrone by means of a Grignard reaction us ingethylinylmagnesium bromide as nucleophile.This derivative was used as a synthon for the formation of a hybrid triazole composed of a steroid and a carbohydrate-derived azide (3-azide-1,2:5,6-diisopropylidene-α-D-glucofuranose) under classical thermal conditions. The reaction products were characterized by infrared spectroscopy, hydrogen and carbon 13 nuclear magnetic resonance

Triazoles derivados de colesterol y diosgenina

Los conjugados de esteroides constituyen una extensa e importante clase de compuestos policíclicos biológicamente activos que se utilizan ampliamente con fines terapéuticos. En este trabajo, se describe la síntesis de dos tipos de derivados de esteroides unidos al núcleo de 1,2,3-triazol. Estos nuevos triazoles fueron sintetizados a través de una reacción de cicloadición [3 + 2] catalizada por un oxido de Cu/Al, entre la 4-bromobencilazida generada in situ y los derivados de colesterol y diosgenina O-propargilados. Con esta síntesis “click” multicomponente, los conjugados de triazol-esteroides se obtuvieron con buenos rendimientos y ambos compuestos fueron caracterizados por espectroscopía de infrarrojo (IR), y resonancia magnética nuclear de una y dos dimensiones (RMN).Steroid conjugates constitute an extensive and important class of biologically active polycyclic compounds that are widely used for therapeutic purposes. In this work, an expedient synthesis of two types of 1,2,3-triazole-linked steroids is described. These novel triazoles were prepared via Cu/Al mixed oxide-catalyzed [3 + 2] cycloaddition of in situ-generated 4-bromobenzylazide and either O-propargylated cholesterol or diosgenin. With this multicomponent click synthesis, the desired triazol-steroids conjugates were obtained in good yields and the compounds were properly characterized by infrared (IR), and two-dimensional nuclear magnetic resonance (NMR)