Delfino Chamorro‐Arenas

Benemérita Universidad Autónoma de Puebla

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Fernando Sartillo‐Piscil

Benemérita Universidad Autónoma de Puebla

Leticia Quintero

Benemérita Universidad Autónoma de Puebla

Herbert Höpfl

Universidad Autónoma del Estado de Morelos

Lilia Fuentes

Benemérita Universidad Autónoma de Puebla

Urbano Osorio-Nieto

Pontificia Universidad Católica de Chile

Silvano Cruz‐Gregorio

Benemérita Universidad Autónoma de Puebla

Alejandro A. Nolasco‐Hernández

Benemérita Universidad Autónoma de Puebla

Isabel Martínez‐Alcalá

Universidad Católica San Antonio de Murcia

Félix Luna

Pontifical Catholic University of Peru

Liliana Mendieta

Centro de Investigación Biomédica en Red

Cooperative Institutions

Benemérita Universidad Autónoma de Puebla

Indian Institute of Technology Guwahati

Centre of Biomedical Research

Pandit Bhagwat Dayal Sharma Post Graduate Institute of Medical Sciences

Atatürk University

Universidade Nova de Lisboa

Birla Institute of Technology and Science, Pilani

Pusan National University

Université Rennes 2

Université de Rennes

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Antidepressant and Neuroprotective Effects of 3-Hydroxy Paroxetine, an Analog of Paroxetine in Rats

The International Journal of Neuropsychopharmacology (2022)

Pedro Efraín Hernández-Arrambide Alan Carrasco‐Carballo Irving Parra Delfino Chamorro‐Arenas Isabel Martínez‐Alcalá

Abstract Background Paroxetine (PX) is a widely used antidepressant with side effects such as weakness, dizziness, and trouble sleeping. In search of novel compounds with better efficacy and fewer side effects, we synthesized 3HPX, a hydroxylated analog of PX, and compared the 2 in silico for their pharmacokinetic and binding properties and in vivo for their antidepressant and potential neuroprotective effects. Methods In silico studies compared pharmacological properties as well as interactions of PX and 3HPX with the serotonin transporter. In vivo studies utilized an animal model of comorbid depression-Parkinson disease. Adult male Wistar rats were injected (sterotaxically) with lipopolysaccharide in the striatum (unilaterally), followed by 14 days of once-daily injections (i.p.) of 10 mg/kg PX or 3HPX. Animals were tested for motor asymmetry and locomotor activity as well as indices of anhedonia and helplessness using sucrose preference and forced swim tests, respectively. Brains of these animals were collected after the last test, and tyrosine hydroxylase–positive neurons in substantia nigra pars compacta and Iba-1–positive stained microglia in ipsilateral striatum were measured. Results In silico findings indicated that 3HPX could bind stronger to serotonin transporter and also have a better clearance and hence less toxicity compared with PX. In vivo results revealed a more effective reversal of immobility in the swim test, substantial increase in tyrosine hydroxylase–positive cells in the substantia nigra pars compacta, and more ramified Iba-1+ cells by 3HPX compared with PX. Conclusion The findings suggest superior effectiveness of 3HPX as an antidepressant and neuroprotectant compared with PX and hence potential utility in Parkinson disease depression co-morbidity.

Pars compacta

Paroxetine

10.1093/ijnp/pyac077

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Diastereoconvergent Synthesis of (–)‐Paroxetine

European Journal of Organic Chemistry (2017)

Delfino Chamorro‐Arenas Lilia Fuentes Leticia Quintero Silvano Cruz‐Gregorio Herbert Höpfl

A diastereoconvergent approach to (–)‐paroxetine from diastereomeric 3,4‐epoxy‐2‐piperidones is reported. For this synthesis, a regioselective and stereodivergent Cu I ‐catalyzed epoxide‐ring‐opening reaction of epoxyamide precursors to give the 4‐(4‐fluorophenyl)‐2‐piperidone skeleton with the correct absolute configuration is crucial. Using CuBr · SMe 2 as a catalyst, the epoxide‐ring‐opening reaction takes place with inversion of configuration; the configuration is retained when CuI is used.

Diastereomer

Absolute Configuration

10.1002/ejoc.201700658

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Citations (8)

Transition‐Metal‐Free Multiple Functionalization of Piperidines to 4‐Substituted and 3,4‐Disubstituted 2‐Piperidinones

Chemistry - A European Journal (2019)

Delfino Chamorro‐Arenas Alejandro A. Nolasco‐Hernández Lilia Fuentes Leticia Quintero Fernando Sartillo‐Piscil

Abstract Remote and multiple functionalization of piperidines without the use of transition‐metal catalysts and elaborate directing groups is one of the major challenges in organic synthesis. Herein is reported an unprecedented two‐step protocol that enables the multiple functionalization of piperidines to either 4‐substituted or trans ‐3,4‐disubstituted 2‐piperidones. First, by exploiting the duality of TEMPO reactivity, which under oxidative and thermal conditions fluctuates between cationic and persistent‐radical form, a novel multiple C(sp 3 )‐H oxidation of piperidines to α,β‐unsaturated 2‐piperidones was developed. Second, the intrinsic low reactivity of the unsaturated piperidones toward conjugated Grignard additions was overcome by using trimethylsilyl chloride (TMSCl) as Lewis acid. Subsequently, conjugated Grignard addition/electrophilic trapping protocol provided substituted 2‐piperidone intermediates, some of which were then transformed into pharmaceutical alkaloids.

Surface Modification

Cationic polymerization

Reactivity

Trimethylsilyl

10.1002/chem.201905262

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CCDC 1541565: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Delfino Chamorro‐Arenas Lilia Fuentes Leticia Quintero Silvano Cruz‐Gregorio Herbert Höpfl

10.5517/ccdc.csd.cc1nr3xf

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CCDC 1487053: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Urbano Osorio-Nieto Delfino Chamorro‐Arenas Leticia Quintero Herbert Höpfl Fernando Sartillo‐Piscil

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1lxdgc

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CCDC 1487052: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Urbano Osorio-Nieto Delfino Chamorro‐Arenas Leticia Quintero Herbert Höpfl Fernando Sartillo‐Piscil

10.5517/ccdc.csd.cc1lxdfb

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Transition Metal-Free Selective Double sp³ C–H Oxidation of Cyclic Amines to 3-Alkoxyamine Lactams

The Journal of Organic Chemistry (2016)

Urbano Osorio-Nieto Delfino Chamorro‐Arenas Leticia Quintero Herbert Höpfl Fernando Sartillo‐Piscil

The first chemical method for selective dual sp3 C–H functionalization at the alpha-and beta positions of cyclic amines to their corresponding 3-alkoxyamine lactams is reported. Unlike traditional Cα–H oxidation of amines to amides mediated by transition metals, the present protocol, which involves the use of NaClO2/TEMPO/NaClO in either aqueous or organic solvent, not only allows the Cα–H oxidation but also the subsequent functionalization of the unreactive β-methylene group in an unprecedented tandem fashion and using environmentally friendly reactants.

Cyclic amines

10.1021/acs.joc.6b01566

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Citations (36)

Frontispiece: Transition‐Metal‐Free Multiple Functionalization of Piperidines to 4‐Substituted and 3,4‐Disubstituted 2‐Piperidinones

Chemistry - A European Journal (2020)

Delfino Chamorro‐Arenas Alejandro A. Nolasco‐Hernández Lilia Fuentes Leticia Quintero Fernando Sartillo‐Piscil

The C−H functionalization of unreactive sp3 carbon atoms under transition-metal-free conditions contribute, not only to the invention of novel methodologies and synthetic strategies, but also to the development of greener and more sustainable organic chemical processes. With this aim in mind, the direct functionalization of simple piperidines into substituted 2-piperidones and relevant pharmaceutical alkaloids was achieved thought the development of two transition-metal-free cascade reactions. For more information see the Communication by F. Sartillo-Piscil et al. on page 4671 ff.

Surface Modification

Chemical modification

10.1002/chem.202082163

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CCDC 1541564: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Delfino Chamorro‐Arenas Lilia Fuentes Leticia Quintero Silvano Cruz‐Gregorio Herbert Höpfl

10.5517/ccdc.csd.cc1nr3wd

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Selective, Catalytic, and Dual C(sp³)–H Oxidation of Piperazines and Morpholines under Transition-Metal-Free Conditions

The Journal of Organic Chemistry (2018)

Delfino Chamorro‐Arenas Urbano Osorio-Nieto Leticia Quintero Luis Hernández-García Fernando Sartillo‐Piscil

By using cheap and innocuous reagents, such as NaClO2, NaOCl, and catalytic amounts of TEMPO, a new environmentally friendly protocol for the selective and catalytic TEMPO C(sp3)–H oxidation of piperazines and morpholines to 2,3-diketopiperazines (2,3-DKP) and 3-morpholinones (3-MPs), respectively, has been developed. This novel direct access to 2,3-DKP from piperazines provides significant advantages over the traditional N-monoacylation/intramolecular C–N cyclization procedure. Additionally, by modulating the amounts of TEMPO, 2-alkoxyamino-3-morpholinone can be prepared from morpholine derivatives, which would enable further functionalization at the C2 position of the morpholine skeleton.

10.1021/acs.joc.8b02564

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Citations (31)