Derivados de cromano y sus usos como inhibidores de la actividad de las proteínas desacoplantes

Derivados de cromano y sus usos como inhibidores de la actividad de las proteínas desacoplantes. Compuestos derivados del cromano, que presentan la fórmula general (I), donde R1 y R2, son iguales o diferentes entre sí, y están representados por un átomo de hidrógeno (H) o un grupo alquilo (C1-C8); R3 está representado por un átomo de H, un halógeno, un grupo arilo o un grupo -COOR5; donde R5 es alquilo (C1-C4) o un alquilarilo; y R4 está representado por un átomo de hidrógeno (H), un grupo alquilarilo o un grupo alquilo (C1-C8), lineal o ramificado. Así como sus diferentes usos, más concretamente en la identificación de compuestos terapéuticos, como compuestos reguladores de las proteínas desacoplantes o su uso terapéutico para el tratamiento de diferentes enfermedades y dolencias que cursen con un aumento en la actividad de dichas proteínas.Peer reviewedConsejo Superior de Investigaciones Científicas (España

Derivados de cromano y sus usos como inhibidores de la actividad de las proteínas desacoplantes

Derivados de cromano y sus usos como inhibidores de la actividad de las proteínas desacoplantes. Compuestos derivados del cromano, que presentan la fórmula general (I), donde R1 y R2, son iguales o diferentes entre sí, y están representados por un átomo de hidrógeno (H) o un grupo alquilo (C1-C8); R3 está representado por un átomo de H, un halógeno, un grupo arilo o un grupo –COOR5; donde R5 es alquilo (C1-C4) o un alquilarilo; y R4 está representado por un átomo de hidrógeno (H), un grupo alquilarilo o un grupo alquilo (C1-C8), lineal o ramificado. Así como sus diferentes usos, más concretamente en la identificación de compuestos terapéuticos, como compuestos reguladores de las proteínas desacoplantes o su uso terapéutico para el tratamiento de diferentes enfermedades y dolencias que cursen con un aumento en la actividad de dichas proteínas.Peer reviewedConsejo Superior de Investigaciones Científicas (CSIC).A1 Solicitud de patentes con informe sobre el estado de la técnic

Base-Induced Sulfoxide-Sulfenate Rearrangement of 2-Sulfinyl Dienes for the Regio- and Stereoselective Synthesis of Enantioenriched Dienyl Diols

The base-induced [2,3]-sigmatropic rearrangement of a series of enantiopure 2-sulfinyl dienes has been examined and optimized using a combination of NaH and iPrOH. The reaction takes place by allylic deprotonation of the 2-sulfinyl diene to give a bis-allylic sulfoxide anion intermediate that after protonation undergoes sulfoxide-sulfenate rearrangement. Different substitution at the starting 2-sulfinyl dienes has allowed us to study the rearrangement finding that a terminal allylic alcohol is determinant to achieve complete regioselectivity and high enantioselectivities (90:10-95:5) with the sulfoxide as the only element of stereocontrol. Density functional theory (DFT) calculations provide an interpretation of these resultsThe authors thank MICINN (PID2019-107380GB-I00) for financial support. M.M. thanks Erasmus+ program for an internship. The authors thank Paula López and Fernando Romero for their initial experiments with compounds 8, 9, and 11. They also thank the Centro de Computación Científica at the UAM for their generous allocation of computer tim

Diastereodivergent Synthesis of 2‑Ene-1,4-hydroxy Sulfides from 2‑Sulfinyl Dienes via Tandem Sulfa-Michael/Sulfoxide-Sulfenate Rearrangement

The highly diastereoselective sulfa-Michael addition of thiolates to enantiopure 2-sulfinyl dienes leads to anti or syn 2- ene-1,4-hydroxy sulfides in good yields and selectivities dependent on the reaction conditions in a diastereodivergent process. Synthetic applications of these enantiopure hydroxy sulfides by subsequent sigmatropic rearrangements have been outlined.This research was supported by PID2019-107380GB-100 and CTQ2016-77555-C2-2-R.Peer reviewe

Synthesis of chiral sulfinamido-sulfonamides and their evaluation as ligands for the enantioselective ethylation of aldehydes

10 pages, 2 figures, 2 tables.-- Printed version published May 2, 2009.A family of chiral sulfinamido-sulfonamide ligands have been synthesized from sulfinimines and has been evaluated as ligands for the enantioselective addition of diethylzinc to aldehydes with Ti(O(i)Pr)4. The structure of these diamino compounds has been systematically modified to optimize the results.This research was supported by DGI MEC (CTQ2006-04522/BQU) and CM (S-SAL-0249-2006).Peer reviewe

From Allylic Sulfoxides to Allylic Sulfenates: Fifty Years of a Never-Ending [2,3]-Sigmatropic Rearrangement

The [2,3]-sigmatropic rearrangement of allylic sulfoxides to allylic sulfenates is a reversible process, generally shifted toward the sulfoxide. In the presence of thiophiles, the sulfenate is trapped, and allylic alcohols are obtained under mild conditions. In most cases, a good transfer of stereochemical information through an ordered transition state is obtained. Furthermore, the ease of coupling this process with other versatile, stereocontrolled reactions has enhanced the usefulness of this protocol. This review aims to provide a comprehensive survey of this rearrangement and its application in the synthesis of natural and bioactive products.This research was supported by MINECO (Spain) (CTQ2013- 46459-C2-02-P, CTQ2016-77555-C2-2-R, CTQ2016-81797- REDC). We are grateful to Dr. Carmen de la Torre (IQOGCSIC) and Dr. Miguel Ángel Sierra (UCM) for encouragement and supportPeer Reviewe

Sulfinyl-mediated stereoselective functionalization of acyclic conjugated dienes

The chemo- and stereocontrolled functionalization of conjugated sulfinyl dienes in a cascade process that involves a Michael-type addition, isomerization of a double bond and a [2,3]-sigmatropic rearrangement is reported. Enantioenriched 1,4-diol and 1,4-aminoalcohol derivatives are obtained in a very straightforward manner. Further functionalization of these structures, including highly stereoselective epoxidation, dihydroxylation and the stereodivergent synthesis of several polyols in a controlled fashion is describedThis research was supported by CTQ2016-77555-C2-2-R and MICINN (CTQ2009-07752). We also thank CM for additional support to MU and MEC for a fellowship to I.CPeer reviewe

Oxidative reactions of sulfinyl dienes as an entry to functionalized carbohydrate-like products and furans

Oxidative cleavage (OsO/NaIO) of a monoprotected dihydroxy sulfinyl diene affords a lactol, readily transformed into a sulfinyl pyranose. Alternatively, base promoted intramolecular cyclization of a lactol derived carbamate to a bicyclic oxazolidinone followed by simple transformations leads to an amino sulfonyl pyranose. In contrast, ozonolysis of a variety of hydroxy sulfinyl dienes leads to fair yields of 3-sulfinyl furans in a single step.This research was supported by grants CTQ2009-07752 and CTQ2016-77555-C2-2-R. We thank CSIC-FSE for a doctoral fellowship to A.C. and a postdoctoral contract to I.O.Peer Reviewe

Evidence for "stable" organocopper intermediates in the reaction between Me2CuLi[middle dot]LiI and allylic sulfinyl mesylates.

The addition of Me2CuLi[middle dot]LiI to acyclic allylic sulfinyl mesylates bearing a phenyl functionality in the molecule gives rise to chiral allenes 4 and 11 in variable yields and optical purities, presumably via an unusually stable [sigma]-copper(III) species.Peer Reviewedhttp://deepblue.lib.umich.edu/bitstream/2027.42/29897/1/0000254.pd