Jorge Gómez-Carpintero

Universidad Complutense de Madrid

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Juan F. González

Universidad Politécnica de Cartagena

J. Carlos Menéndez

Universidad Complutense de Madrid

Damiano Rocchi

Universidad Complutense de Madrid

J. Domingo Sánchez

Universidad Complutense de Madrid

Vellaisamy Sridharan

Central University of Jammu

Víctor González‐Ruiz

University of Basel

M. Antonia Martín

Universidad Complutense de Madrid

Ana I. Olives

Universidad Complutense de Madrid

Jegathalaprathaban Rajesh

Saveetha University

Clara Cabrero

Universidad Complutense de Madrid

Cooperative Institutions

Universidad Complutense de Madrid

Madurai Kamaraj University

Central University of Jammu

University of Hyderabad

SASTRA University

Tamil University

University of Jammu

Osaka University

Aix-Marseille Université

Saveetha University

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Sustainable Access to Acridin-9-(10H)ones with an Embedded m-Terphenyl Moiety Based on a Three-Component Reaction

Molecules (2020)

Damiano Rocchi Jorge Gómez-Carpintero Juan F. González J. Carlos Menéndez

A Ce(IV)-catalyzed three-component reaction between chalcones, anilines and β-ketoesters followed by a microwave-assisted thermal cyclization afforded 1,3-diaryl-1,2-dihydroacridin-9(10H)-ones. Their microwave irradiation in nitrobenzene, acting both as solvent and oxidant, afforded fully unsaturated 1,3-diarylacridin-9(10H)-ones, which combine acridin-9-(10H)one and m-terphenyl moieties. Overall, the route generates three C-C and one C-N bond and has the advantage of requiring a single chromatographic separation.

Moiety

Terphenyl

Nitrobenzene

Component (thermodynamics)

10.3390/molecules25235565

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Citations (2)

A sequential multistep process for the fully mechanochemical, one-pot synthesis of the antiepileptic drug rufinamide

Green Chemistry Letters and Reviews (2022)

Jorge Gómez-Carpintero Clara Cabrero J. Domingo Sánchez Juan F. González J. Carlos Menéndez

Mechanochemistry is a powerful tool to develop environmentally benign syntheses of active pharmaceutical ingredients. In this context, we report here the synthesis of the anti-epileptic agent rufinamide through a one-pot sequential multi-component approach, which was fully carried out applying a ball milling method. This solid-state synthesis of rufinamide has proved to be more efficient in terms of sustainability than the equivalent conventional synthetic process in solution. The mechanochemical method presents several advantages such as shorter reaction times, pot economy, the absence of external heating and solvent use. The ball milling-based synthesis of rufinamide has shown excellent green metrics and it is in agreement with several principles of Green Chemistry.

Mechanochemistry

Antiepileptic drug

10.1080/17518253.2022.2123717

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Citations (9)

Mechanochemical Synthesis of Primary Amides

The Journal of Organic Chemistry (2021)

Jorge Gómez-Carpintero J. Domingo Sánchez Juan F. González J. Carlos Menéndez

Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.

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Primary (astronomy)

Mechanochemistry

10.1021/acs.joc.1c02350

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Citations (33)

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

ACS Combinatorial Science (2018)

Damiano Rocchi Juan F. González Jorge Gómez-Carpintero Víctor González‐Ruiz M. Antonia Martín

The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.

Stereocenter

Aromatization

Terphenyl

Domino

Atom economy

Sequence (biology)

10.1021/acscombsci.8b00137

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Citations (13)

Twenty-first century antiepileptic drugs. An overview of their targets and synthetic approaches

European Journal of Medicinal Chemistry (2024)

J. Domingo Sánchez Jorge Gómez-Carpintero Juan F. González J. Carlos Menéndez

The therapeutic use of the traditional drugs against epilepsy has been hindered by their toxicity and low selectivity. These limitations have stimulated the design and development of new generations of antiepileptic drugs. This review explores the molecular targets and synthesis of the antiepileptic drugs that have entered the market in the 21st century, with a focus on manufacturer synthesis.

Antiepileptic drug

10.1016/j.ejmech.2024.116476

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Citations (3)

Antioxidants as Molecular Probes: Structurally Novel Dihydro-m-Terphenyls as Turn-On Fluorescence Chemodosimeters for Biologically Relevant Oxidants

Antioxidants (2020)

Víctor González‐Ruiz Jegathalaprathaban Rajesh Ana I. Olives Damiano Rocchi Jorge Gómez-Carpintero

One interesting aspect of antioxidant organic molecules is their use as probes for the detection and quantitation of biologically relevant reactive oxidant species (ROS). In this context, a small library of dihydroterphenyl derivatives has been synthesised and studied as fluorescent chemodosimeters for detecting reactive oxygen species and hypochlorite. The fluorescence quantum yields of these molecules are negligible, while the corresponding aromatized compounds formed upon oxidation show moderate to high native fluorescence, depending on their structures. The fluorescence signal is quickly developed in the presence of trace amounts of the probe and the analytes in acetonitrile media at room temperature, with good analytical figures. ROS detection in aqueous media required incubation at 37 °C in the presence of horseradish peroxidase, and was applied to glucose quantitation by coupling glucose oxidation by O2 to fluorescence detection of H2O2. The mild reaction conditions and sensitive fluorescent response lead us to propose dihydroterphenyls with an embedded anthranilate moiety as chemosensors/chemodosimeters for ROS detection.

Moiety

Hypochlorite

Horseradish peroxidase

10.3390/antiox9070605

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Citations (5)