Menéndez Ramos, José Carlos

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First Name
José Carlos
Last Name
Menéndez Ramos
Universidad Complutense de Madrid
Faculty / Institute
Química en Ciencias Farmacéuticas
Química Orgánica
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Now showing 1 - 10 of 20
  • Publication
    Bisavenathramide Analogues as Nrf2 Inductors and Neuroprotectors in In Vitro Models of Oxidative Stress and Hyperphosphorylation
    (MDPI, 2021-06-10) Cores Esperón, Ángel; Abril, Sheila; Michalska, Patrycja; Duarte, Pablo; Olives Barba, Ana Isabel; Martín Carmona, María Antonia; Villacampa Sanz, Mercedes; León, Rafael; Menéndez Ramos, José Carlos
    Oxidative stress is crucial to the outbreak and advancement of neurodegenerative diseases and is a common factor to many of them. We describe the synthesis of a library of derivatives of the 4-arylmethylen-2-pyrrolin-5-one framework by sequential application of a three-component reaction of primary amines, β-dicarbonyl compounds, and α-haloketones and a Knoevenagel condensation. These compounds can be viewed as cyclic amides of caffeic and ferulic acids, and are also structurally related to the bisavenanthramide family of natural antioxidants. Most members of the library showed low cytotoxicity and good activity as inductors of Nrf2, a transcription factor that acts as the master regulator of the antioxidant response associated with activation of the antioxidant response element (ARE). Nrf2-dependent protein expression was also proved by the significant increase in the levels of the HMOX1 and NQO1 proteins. Some compounds exerted neuroprotective properties in oxidative stress situations, such as rotenone/oligomycin-induced toxicity, and also against protein hyperphosphorylation induced by the phosphatase inhibitor okadaic acid. Compound 3i, which can be considered a good candidate for further hit-to-lead development against neurodegenerative diseases due to its well-balanced multitarget profile, was further characterized by proving its ability to reduce phosphorylated Tau levels.
  • Publication
    Desarrollo del aula virtual como soporte del aprendizaje flexible, de las competencias relacionadas con la determinación estructural de compuestos orgánicos
    (2019-04-04) González Matilla, Juan Francisco; Cuesta Elosegui, Elena de la; Menéndez Ramos, José Carlos; Villacampa Sanz, Mercedes; Ramos García, María teresa; Cores Esperón, Ángel
    La mejora en la actividad docente y la eficacia del tiempo dedicado al aprendizaje por el alumno, están estrechamente ligadas al tiempo que dedica el alumno al aprendizaje fuera del aula. Con el desarrollo y avance de las TIC, en los últimos tiempos ha ganado terreno una práctica de aprendizaje que tiene su origen en la educación a distancia y que se conoce hoy como e-learning, educación virtual o, educación en línea. En este sentido hemos diseñado y elaborado una serie de fichas de problemas sobre determinación estructural de compuestos orgánicos. En este proyecto también se han elaborado vídeos tutoriales donde se indican las pautas necesarias para resolver los problemas de determinación estructural.
  • Publication
    Empleo de Software libre para la enseñanza en el área de la Química Orgánica
    (2022) González Matilla, Juan Francisco; Gómez-Carpintero Jiménez, Jorge; Menéndez Ramos, José Carlos; Ramos García, María Teresa; Villacampa Sanz, Mercedes; Sanchez Cebrián, Juan Domingo
  • Publication
    Fluorescence Sensors Based on Hydroxycarbazole for the Determination of Neurodegeneration-Related Halide Anions
    (MPDI, 2022-03-14) González Ruiz, Víctor; Cores, Ángel; Caja, M. Mar; Sridharan, Vellaisamy; Villacampa, Mercedes; Martín, M. Antonia; Olives Barba, Ana Isabel; Menéndez Ramos, José Carlos
    The environmental presence of anions of natural origin or anthropogenic origin is gradually increasing. As a tool to tackle this problem, carbazole derivatives are an attractive gateway to the development of luminescent chemosensors. Considering the different mechanisms proposed for anion recognition, the fluorescence properties and anion-binding response of several newly synthesised carbazole derivatives were studied. Potential anion sensors were designed so that they combined the native fluorescence of carbazole with the presence of hydrogen bonding donor groups in critical positions for anion recognition. These compounds were synthesised by a feasible and non-expensive procedure using palladium-promoted cyclodehydrogenation of suitable diarylamine under microwave irradiation. In comparison to the other carbazole derivatives studied, 1-hydroxycarbazole proved to be useful as a fluorescent sensor for anions, as it was able to sensitively recognise fluoride and chloride anions by establishing hydrogen bond interactions through the hydrogen atoms on the pyrrolic nitrogen and the hydroxy group. Solvent effects and excited-state proton transfer (ESPT) of the carbazole derivatives are described to discard the role of the anions as Brönsted bases on the observed fluorescence behaviour of the sensors. The anion–sensor interaction was confirmed by 1H-NMR. Molecular modelling was employed to propose a mode of recognition of the sensor in terms of complex stability and interatomic distances. 1-hydroxycarbazole was employed for the quantitation of fluoride and chloride anions in commercially available medicinal spring water and mouthwash samples.
  • Publication
    Mechanochemical Synthesis of Primary Amides
    (ACS Publications, 2021-10-01) Gómez-Carpintero Jiménez, Jorge; Sánchez Cebrián, J. Domingo; González Matilla, Juan Francisco; Menéndez Ramos, José Carlos
    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.
  • Publication
    Ethyl 4,4''-Dibromo-5'-(butylamino)-2',6'-dinitro-[1,1':3',1''-terphenyl]-4'-carboxylate
    (MDPI, 2015-03-18) Rocchi, Damiano; González, Juan F.; Menéndez Ramos, José Carlos
    Ethyl 4,4''-Dibromo-5'-(butylamino)-2',6'-dinitro-[1,1':3',1''-terphenyl]-4'- carboxylate (2) which is a m-terphenyl derivative containing an hexasubstituted, highly functionalized substituted benzene core, has been synthesized.
  • Publication
    Multicomponent Domino Synthesis, Anticancer Activity and Molecular Modeling Simulation of Complex Dispirooxindolopyrrolidines
    (MDPI, 2018-05-05) Arumugam, Natarajan; Almansour, Abdulrahman I.; Suresh Kumar, Raju; Govindasami, Periyasami; Al-thamili, Dhaifallah; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali; Mahalingam, S. M.; Thangamani, Shankar; Menéndez Ramos, José Carlos
    A series of spirooxindolopyrrolidine fused N -styrylpiperidone heterocyclic hybrids has been synthesized in excellent yield via a domino multicomponent protocol that involves one-pot three component 1,3-dipolar cycloaddition and concomitant enamine reactions performed in an inexpensive ionic liquid, namely 1-butyl-3-methylimidazolium bromide ([bmim]Br). Compounds thus synthesized were evaluated for their cytotoxicity against U-937 tumor cells. Interestingly; compounds 5i and 5m exhibited a better cytotoxicity than the anticancer drug bleomycin. In ddition; the effect of the synthesized compounds on the nuclear morphology of U937 FaDu cells revealed that treatment with compounds 5a–m led to their apoptotic cell death.
  • Publication
    Approaches to the Potential Therapy of COVID-19: A General Overview from the Medicinal Chemistry Perspective
    (MPDI, 2022-01-20) Menéndez Ramos, José Carlos
    In spite of advances in vaccination, control of the COVID-19 pandemic will require the use of pharmacological treatments against SARS-CoV2. Their development needs to consider the existence of two phases in the disease, namely the viral infection and the inflammatory stages. The main targets for antiviral therapeutic intervention are: (a) viral proteins, including the spike (S) protein characteristic of the viral cover and the viral proteases in charge of processing the polyprotein arising from viral genome translation; (b) host proteins, such as those involved in the processes related to viral entry into the host cell and the release of the viral genome inside the cell, the elongation factor eEF1A and importins. The use of antivirals targeted at host proteins is less developed but it has the potential advantage of not being affected by mutations in the genome of the virus and therefore being active against all its variants. Regarding drugs that address the hyperinflammatory phase of the disease triggered by the so-called cytokine storm, the following strategies are particularly relevant: (a) drugs targeting JAK kinases; (b) sphingosine kinase 2 inhibitors; (c) antibodies against interleukin 6 or its receptor; (d) use of the traditional anti-inflammatory corticosteroids.
  • Publication
    A Sustainable Approach to the Stereoselective Synthesis of Diazaheptacyclic Cage Systems Based on a Multicomponent Strategy in an Ionic Liquid
    (MDPI, 2016) Suresh Kumar, Raju; Almansour, Abdulrahman; Arumugam, Natarajan; Altaf, Mohammad; Menéndez Ramos, José Carlos; Kumar, Raju; Osman, Hasnah
    The microwave-assisted three-component reactions of 3,5-bis(E)-arylmethylidene] tetrahydro-4(1H)-pyridinones, acenaphthenequinone and cyclic α-amino acids in an ionic liquid, 1-butyl-3-methylimidazolium bromide, occurred through a domino sequence affording structurally intriguing diazaheptacyclic cage-like compounds in excellent yields.
  • Publication
    Bifunctional carbazole derivatives for simultaneous therapy and fluorescence imaging in prion disease murine cell models
    (Elsevier, 2022-11-15) Staderini, Matteo; Vanni, Silvia; Colini Baldeschi, Arianna; Zattoni, Marco; Celauro, Luigi; Ferracin, Chiara; Bistaffa, Edoardo; Moda, Fabio; Pérez, Daniel I.; Martínez, Ana; Martín Carmona, María Antonia; Martín Cámara, Olmo; Cores Esperón, Ángel; Bianchini, Giulia; Kammerer, Robert; Menéndez Ramos, José Carlos; Legname, Giuseppe; Bolognesi, Maria Laura
    Prion diseases are characterized by the self-assembly of pathogenic misfolded scrapie isoforms (PrPSc) of the cellular prion protein (PrPC). In an effort to achieve a theranostic profile, symmetrical bifunctional carbazole derivatives were designed as fluorescent rigid analogues of GN8, a pharmacological chaperone that stabilizes the native PrPC conformation and prevents its pathogenic conversion. A focused library was synthesized via a four- step route, and a representative member was confirmed to have native fluorescence, including a band in the near- infrared region. After a cytotoxicity study, compounds were tested on the RML-infected ScGT1 neuronal cell line, by monitoring the levels of protease-resistant PrPSc. Small dialkylamino groups at the ends of the molecule were found to be optimal in terms of therapeutic index, and the bis-(dimethylaminoacetamido)carbazole derivative 2b was selected for further characterization. It showed activity in two cellClines infected with the mouse-adapted RML strain (ScGT1 and ScN2a). Unlike GN8, 2b did not affect PrP levels, which represents a potential advantage in terms of toxicity. Amyloid Seeding Assay (ASA) experiments showed the capacity of 2b to delay the aggregation of recombinant mouse PrP. Its ability to interfere with the amplification of the scrapie RML strain by Protein Misfolding Cyclic Amplification (PMCA) was shown to be higher than that of GN8, although 2b did not inhibit the amplification of human vCJD prion. Fluorescent staining of PrPSc aggregates by 2b was confirmed in living cells. 2b emerges as an initial hit compound for further medicinal chemistry optimization towards strain- independent anti-prion compounds.