Journal of the Mexican Chemical Society最新文献

{"title":"Microwave-Assisted Reactivity of a Fischer Alkynyl Carbene Complex with Benzylidene Anilines","authors":"José Francisco Delgado Reyes, A. Feliciano, Miguel A. Vázquez, Iván Velazco‐Cabral, Juan Luis Vazquez Vazquez, Luis J. Benítez‐Puebla, Salvador Mastachi, Selene Lagunas-Rivera, M. García-Revilla","doi":"10.29356/jmcs.v68i1.1863","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.1863","url":null,"abstract":"The reaction between the Fischer carbene complex (CO)5Cr=C(OEt)CºCPh and various benzylidene anilines RCH=NR1 was promoted by microwave irradiation, generating stable cross-conjugated metallahexatrienes in 45-70 % yield. Compared to conventional heating, the present conditions provided shorter reaction times with moderate yields. The geometrical configuration and the most stable conformation for each of the Fischer carbene complexes and their oxidation products were established by NMR and DFT analysis. The reaction mechanism was explored by DFT calculations of the potential energy surface, suggesting a 1,4-addition/ring closure/electrocyclic opening cascade process.   Resumen. Se reporta la reactividad entre el carbeno de Fischer (CO)5Cr=C(OEt)CºCPh y las bencilidén anilinas, RCH=NR1, empleando irradiación de microondas. Los resultados indican que el calentamiento por microondas generó metalohexatrienos cruzados estables en rendimientos de 45-70 %, mostrando además, que los nuevos complejos se obtienen en tiempos de reacción más cortos y rendimientos moderados en comparación con las condiciones de calentamiento convencional. La configuración geométrica y la conformación más estable para los complejos carbénicos de Fischer y de sus derivados oxidados fueron establecidos por medio de RMN y DFT. La exploración de la superficie de energía potencial por cálculos DFT mostró que el proceso consistió en una reacción en cascada incluyendo una secuencia de adición-1,4, cierre de anillo y apertura electrocíclica.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"39 23","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139125530","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Carbon Dioxide Capture Using Ionic Liquids Containing Amino Acid-Type Anions. Effect of the Cation, Anion on the Absorption Efficiency","authors":"Rafael Martinez-Palou, Gabriela Barbosa Guevara, Nohra Violeta Gallardo Rivas","doi":"10.29356/jmcs.v68i1.1827","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.1827","url":null,"abstract":"Abstract. In this work, the synthesis of twelve ionic liquids (ILs) with imidazolium cation and amino acid-derived anions and their evaluation as carbon dioxide (CO2) absorbents both, in pure form and aqueous solution (30 % of water) are reported and compared with monoetanolamine (MEA), which is a well-known commercial absorbent with wide application in the Petroleum Industry for capturing acid gases. The effect of both cation substituent features such as length and unsaturation of alkyl chains and amino acid structure at the anion on the CO2 absorption efficiency was studied. All the ILs displayed good CO2 absorption efficiency, being the ILs derived from 1-octyl-3-vinylimidazolium the most effective for this purpose, especially with lysinate anion ([OVI][L]); a capture rate of 1501 mg CO2/mol of IL was achieved when it was diluted in water (30 %).   Resumen. En este trabajo se reporta la síntesis de doce líquidos iónicos (LIs) con el catión imidazolio y los aniones derivados de aminoácidos y la evaluación de estos compuestos como absorbentes de dióxido de carbono (CO2), tanto empleando los absorbentes puros, como en solución acuosa (30 % de agua). Los resultados se comparan con los obtenidos con monoetanolamina (MEA), que es un conocido absorbente comercial con amplia aplicación en la Industria del Petróleo en la captura de gases ácidos. Se estudió el efecto de las características de ambos N-sustituyentes de los cationes, como la longitud y la presencia de insaturación en las cadenas de alquilo y la estructura de aminoácidos que conforman los aniones de los LIs estudiados, en la eficiencia de absorción de CO2. Todos los LIs mostraron una buena eficiencia de absorción de CO2, siendo los LIs derivados del 1-octil-3-vinilimidazolio los más efectivos para este fin, especialmente con el anión lisinato ([OVI][L]); se logró una tasa de captura de 1501 mg CO2/mol de LIs cuando el absorbente se diluyó en agua (30 %).","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"20 6","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139127478","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"DFT and Molecular Docking Studies of Melatonin and Some Analogues Interaction with Xanthine Oxidase as a Possible Antiradical Mechanism","authors":"B. Manzanilla, M. Martínez-Alfaro, J. Robles","doi":"10.29356/jmcs.v68i1.2072","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.2072","url":null,"abstract":"Melatonin (Mel) and some of its active metabolites such as N1-acetyl-5-methoxykynuramine (AMK), N1-acetyl-N2-formyl-5-methoxykynuramine (AFMK), 6-hydroxymelatonin (6OHM), and the analogues Ir and It recently designed by Galano's group, have been studied within density functional theory (DFT). The purpose is to evaluate some plausible mechanisms of action of melatonin's metabolites and analogues with the free radicals (FR): OH ̇, NO ̇2, HOO ̇, and CH3O͘ . We calculated global chemical reactivity descriptors from conceptual DFT to evaluate their antiradical properties. We used water and pentyl ethanoate as solvents to simulate the physiological conditions, modeled via the continuum solvation model based on density (SMD). We assess the following plausible mechanisms: single electrons transfer (SET), hydrogen atom transfer (HAT) and xanthine oxidase (XO) inhibition. We performed our calculations at the M06-2X/6-31+G* level of theory. The results indicate that Mel, AMK, AFMK, 6OHM, It, and Ir are good antiradicals towards the FRs: NO ̇2 and CH3O , while It and Ir could be suitable XO inhibitors. Keywords: Antiradical properties; Density Functional Theory; melatonin; xanthine oxidase; molecular docking.   Resumen. La melatonina (Mel) y algunos de sus metabolitos activos como N1-acetil-5-metoxiquinuramina (AMK), N1-acetil-N2-formil-5-metoxiquinuramina (AFMK), 6-hidroximelatonina (6OHM) y los análogos Ir e It, diseñados recientemente por el grupo de Galano, han sido estudiados con la teoría de funcionales de la densidad (DFT). El propósito es evaluar algunos mecanismos de acción plausibles de los metabolitos y análogos de la melatonina con los radicales libres (FR):OH ̇, NO ̇2, HOO ̇ y CH3O ̇. Calculamos los descriptores de reactividad química global a partir de DFT conceptual para evaluar sus propiedades antirradicales. Usamos agua y etanoato de pentilo como solventes para simular las condiciones fisiológicas, modeladas a través del modelo continuo de solvatación basado en la densidad (SMD). Evaluamos los siguientes mecanismos plausibles: transferencia de electrones individuales (SET), transferencia de átomos de hidrógeno (HAT) e inhibición de la xantina oxidasa (XO). Realizamos nuestros cálculos al nivel de teoría M06-2X/6-31+G*. Los resultados indican que Mel, AMK, AFMK, 6OHM, It e Ir son buenos antirradicales frente a los FRs:  NO ̇2 y CH3O ̇, mientras que It e Ir podrían ser inhibidores adecuados de XO.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"26 26","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139125797","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis, Characterization, and Molecular Docking of Casiopeinas® with Dipeptides as Secondary Ligand; Potential Inhibitors of SARS-Cov-2 Transcendental Proteins","authors":"Luis Gabriel Talavera Contreras, L. F. Hernández-Ayala, Virginia Gómez-Vidales, María Lourdes Villar-Cuevas, Lena Ruiz Azuara","doi":"10.29356/jmcs.v68i1.1849","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.1849","url":null,"abstract":"In this work, the synthesis and characterization of fourteen Casiopeinas® are presented, whose general formulae is [Cu(N-N)(L-L)]NO3, where N-N are 2,2´-bipirydine and 1,10-phenanthroline and some of its methylated derivatives, L-L represent the dipeptides L-Tyrosil-Glycinate or Glycil-L-Tyrosinate. Spectroscopic characterization and DFT studies determine the square planar geometry for the coordination compounds, as well as the influence of the dipeptide on the molecular arrangement of ternary copper(II) compounds. In addition, a molecular docking study was carried out against transcendental proteins of the SARS-CoV-2 virus such as main protease (Mpro) and the RBD Spike-ACE2 complex. Docking studies indicate that all compounds can produce stable adducts with Mpro, obtaining ΔGU values (-9.57 to -6.62 Kcal/mol) similar and superior to those presented by the reference inhibitors [boceprevir (-8.44 Kcal/mol) and remdesivir (-6.62 kcal/mol)], while for the RBD Spike-ACE2 complex obtaining ΔGU values of five (-6.69 to -4.61 in C-terminal region) and three (-8.27 to -6.34 in central region) orders of magnitude higher than those presented by the controls (Boceprevir: ΔGU=-1.98 in C-terminal, ΔGU=-4.97 in central region, Remdesivir: ΔGU=Non interactions in C-terminal, ΔGU=-3.37 in central region). π-alkyl interactions, π -cation, π -stacking, as well as hydrogen bonds and salt bridge bonds occur between the proteins and Casiopeinas®. In Mpro, interactions occur in aminoacids that are part of the enzymes catalytic site. Casiopeinas® interact at the interface of the RDB Spike-ACE2 complex in both, C-terminal and central regions. The obtained results position Casiopeinas® as potential candidates protein inhibitors of the virus that causes COVID-19.   Resumen. En este trabajo, se presenta la síntesis y caracterización de 14 Casiopeinas®, cuya fórmula general es [Cu(N-N)(L-L)]NO3, donde N-N son 2,2´-bipiridina y derivados metilados o 1,10-fenantrolina y análogos con grupos metilo, L-L representan a los dipéptidos L-Tirosil-Glicinato o Glicil-L-Tirosinato. Mediante estudios espectroscópicos y de DFT determinan la geometría cuadrada de los compuestos sintetizados, así como la influencia del dipéptido en el arreglo molecular de los compuestos ternarios de cobre(II). Complementariamente, se realizó un estudio de docking molecular ante proteínas trascendentales del virus SARS-CoV-2 como lo son la proteasa principal (MPro o nsps-3) y el complejo RBD Spike-ACE2. Estudios de docking molecular con la MPro se obtuvieron valores de ΔGU (-9.57 a -6.629) kcal/mol, valores que son similares y superiores a los presentados por los inhibidores de referencia [boceprevir (-8.44 kcal/mol) y remdesivir (-6.62 kcal/mol)], mientras que para el complejo RBD Spike-ACE2 se obtuvieron valores de ΔGU de cinco (-6.69 to -4.61 en región C-terminal) y tres (-8.27 to -6.34 en región central) órdenes de magnitud superiores respectivamente a los presentados por los inhibidores de referencia (","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"11 8","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139125996","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A special Issue for an exemplary Professor: Joaquín Tamariz Mascarúa.","authors":"Gabriel Eduardo Cuevas González Bravo","doi":"10.29356/jmcs.v68i1.2191","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.2191","url":null,"abstract":"","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"40 9","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139456604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Fabrication of a Reactive Functionalized Microfilm with Aromatic Amines Applied to the Growth of Langerhans Cells","authors":"Ignacio A. Rivero Espejel, M. Ávila-Cossío, Victor García-González","doi":"10.29356/jmcs.v68i1.2081","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.2081","url":null,"abstract":"This study reports the synthesis of ultrathin polymeric films through layer-by-layer deposition and covalent cross-linking of poly(2-vinyl-4,4'-dimethylazlactone) and branched poly (ethylene imine) (PEI) which were functionalized with aromatic amines that encompass anilines. To assess the effect of these aromatics molecules on the adhesion and proliferation of Langerhans β-cells, we prepared 35 bilayers of unfunctionalized and functionalized films with aromatic amines, which were characterized in terms of their physical, chemical, and biological properties by a battery of experimental techniques including 1H and 13C, NMR, mass spectrometry, attenuated total reflectance Fourier transform infrared spectroscopy, field emission scanning electron microscopy and cell adhesion and staining. The films were nanometric, transparent, resistant to manipulation, chemically reactive, and highly cytocompatible. We demonstrated that films functionalized with aromatic molecules support the attachment and growth of in vitro Langerhans β-cells. This study provides the basis for a general approach to designing and functionalizing ultrathin films that promote cell growth on surfaces of interest for investigation in cell biology studies and a broad range of other biomedical applications.   Resumen. En este estudio se describe la síntesis de películas poliméricas ultrafinas mediante la técnica de capa por capa y la reticulación covalente de poli(2-vinil-4,4'-dimetilazlactona) y poli etilenimina (PEI) ramificado y, se funcionalizaron con aminas aromáticas que engloba las anilinas. Para evaluar el efecto de estas moléculas aromáticas en la adhesión y proliferación de las células β de Langerhans, se prepararon películas de 35 bicapas y se funcionalizaron con aminas aromáticas; se caracterizaron en términos de sus propiedades físicas, químicas y biológicas mediante una serie de técnicas experimentales que incluyeron 1H y 13C, RMN, espectrometría de masas, espectroscopia de infrarrojo por transformada de Fourier, microscopía electrónica de barrido por emisión de campo y tinción celular. En general, las películas fueron nanométricas, transparentes, resistentes a la manipulación, químicamente reactivas y altamente citocompatibles. Se demostró, además, que las películas funcionalizadas con moléculas aromáticas favorecen la adhesión y el crecimiento de células β in vitro. Este estudio establece las bases de un enfoque general para diseñar y funcionalizar películas ultrafinas, que promuevan el crecimiento celular en superficies de interés, para la investigación en estudios de biología celular y una gama amplia de aplicaciones biomédicas potenciales.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"26 5","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139127163","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"In Vitro and In Silico Studies of Bis-furyl-pyrrolo[3,4-b]pyridin-5-ones on Dengue Virus","authors":"Ivette Morales-Salazar, Carlos E Garduño-Albino, Flora P Montes-Enríquez, A. Gutiérrez-Carrillo, Yareli Rojas-Aguirre, Nancy Viridiana Estrada-Toledo, Jorge Sandoval-Basilio, S. Alcaraz-Estrada, E. Díaz-Cervantes, E. González-Zamora, A. Islas-Jácome","doi":"10.29356/jmcs.v68i1.2103","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.2103","url":null,"abstract":"A series of six bis-furyl-pyrrolo[3,4-b]pyridin-5-ones synthesized via an Ugi-Zhu reaction coupled to a cascade process [aza Diels-Alder cycloaddition/N-acylation/aromatization] were evaluated in vitro against Dengue virus serotype 4 infection, and the Dengue virus replicon system encoding a Renilla luciferase gen reporter. Also, in silico studies on the non-structural protein 3 (NS3), a flavivirus protease comprising an attractive target for development of therapeutic antivirals bound to non-structural protein 2B (NS3-NS2B) were performed. The in vitro results showed that compounds 1a and 1b reduced the expression of Renilla luciferase in 44.2 and 31.6%, respectively. Additionally, the same compounds decreased viral load, thus revealing their potential activity against Dengue virus serotype 4. From in silico simulations, it was developed a NS3-NS2B model, which was used as a target for the studied molecules. Computational results agree with experimental data, showing that 1a is the best ligand. Finally, a pharmacophoric model was computed for NS3-NS2B, which shows that the ligands need two hydrophobic and one hydrophilic fragment. Such results suggest that two out of the six synthesized bis-furyl-pyrrolo[3,4-b]pyridin-5-ones derivatives presents potential antiviral activity against Dengue virus in vitro.   Resumen. Una serie de seis bis-furil-pirrolo[3,4-b]piridin-5-onas sintetizadas vía una reacción Ugi-Zhu acoplada a un proceso en cascada [cicloadición aza Diels-Alder/N-acilación/aromatización] fueron evaluadas in vitro contra infección por el serotipo 4 del virus del dengue y el sistema de replicón del virus del Dengue que codifica un gen reportero de la luciferasa de la Renilla. Además, se realizaron estudios in silico sobre la proteína no estructural 3 (NS3), una proteasa de flavivirus que comprende un blanco atractivo para el desarrollo de antivirales terapéuticos unidos a la proteína no estructural 2B (NS3-NS2B). Los estudios in vitro revelaron que los compuestos 1a y 1b reducen la expresión de Renilla luciferasa en un 44.2 y 31.6%, respectivamente. Adicionalmente, estos compuestos redujeron la carga viral, revelando así su actividad potencial contra el virus del Dengue serotipo 4. Derivado de las simulaciones in silico, se obtuvo un modelo homólogo para NS3-NS2B, el cual fue considerado como blanco de las moléculas estudiadas. Los resultados computacionales correlacionan con los experimentales, mostrando que 1a es el mejor ligando. Finalmente, se generó un modelo farmacofórico para NS3-NS2B, el cual muestra que los ligandos necesitan dos fragmentos hidrofóbicos y uno hidrofílico. Estos resultados demuestran que dos de los seis compuestos que se estudiaron presentan actividad antiviral in vitro.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"54 26","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139125392","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Alpha-glucosidase and Alpha-amylase Inhibitors Derived from Naturally Occurring Prenylated Isoflavones","authors":"Brandón Hernández, María del Carmen Cruz, Omar Gómez, Elvia Becerra, Fabiola Eloisa Jiménez, Aarón Mendieta","doi":"10.29356/jmcs.v68i1.2129","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.2129","url":null,"abstract":"A series of prenylated isoflavones were synthesized to evaluate their inhibitory effect against α-glucosidase and α-amylase enzymes, analyzing the bioisosteric effect of the linear or cyclized prenyl moiety in these benzopyran derivatives. Compound 5a exhibited higher α-glucosidase inhibition (IC50 = 60.5 µM) and lower α-amylase inhibition (IC50 = 85.0 µM) compared to acarbose (IC50 = 527.5 µM for α-glucosidase and 20.1 µM for α-amylase). In contrast, prenylated isoflavone 5c showed higher inhibition in both enzymes (IC50 = 17.6 µM for α-glucosidase and 21.2 µM for α-amylase). This suggests that the attachment of a prenyl moiety to the 7-hydroxy group of isoflavone provides higher inhibition in the enzymes α-glucosidase and α-amylase. Docking studies of compounds 5a and 5c displayed key interactions towards both enzymes. The type of inhibition for 5c was analyzed, where the results indicate a competitive inhibition of both α-glucosidase and α-amylase. Finally, ADMET studies support that compounds 5a and 5c are candidates for the design of novel isoflavones derivatives with antidiabetic potential.   Resumen. Una serie de isoflavonas preniladas se sintetizaron para evaluar su efecto inhibidor sobre las enzimas α-glucosidasa y α-amilasa, analizando el efecto bioisotérico del fragmento prenilo tipo lineal o ciclado en estos benzopiranos derivados. El compuesto 5a exhibió una inhibición alta de α-glucosidasa (CI50 = 60.5 µM) y una inhibición más baja de α-amilasa (CI50 = 85.0 µM, respectivamente) en comparación con acarbosa (CI50 = 527.5 y 20.1 µM). La isoflavona prenilada 5c mostró mayor inhibición en ambas enzimas (CI50 = 17.7 µM para α-glucosidasa y 21.2 µM para α-amilasa). Esto sugiere que la unión del fragmento prenilo al hidroxilo de la posición 7 de la isoflavona ocasiona una mayor inhibición en las enzimas α-glucosidasa y α-amilasa. Los compuestos 5a y 5c mostraron interacciones clave hacia el sitio activo de ambas enzimas, de acuerdo con los cálculos de acoplamiento. Se analizó el tipo de inhibición para 5c, donde los resultados indican una inhibición competitiva tanto de α-glucosidasa como de α-amilasa. Finalmente, los estudios ADMET respaldan que los compuestos 5a and 5c son candidatos para el diseño de nuevos derivados de isoflavonas con potencial antidiabético.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"54 3","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139127996","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis and Evaluation of the Antifungal Sensibility of Novel Thienopyridine 1,2,3-Triazole Derivatives","authors":"Alejandra Ramírez-Villalva, Claudia Cervantes-Rebolledo, Carlos A. González-González, Salvador Mastachi-Loza","doi":"10.29356/jmcs.v68i1.1917","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.1917","url":null,"abstract":"The family of compounds known as azoles are part of most of the antimicrobial drugs used for the treatment of infections. Within this family triazoles have been extensively studied as pharmacophores with very promising results. In this work, four novel trisubstituted 1,2,3-triazole compounds with a thienopyridine moiety (1a,b; 2a,b) were synthesized through an azide-enolate 1,3-dipolar cycloaddition. Their cheminformatic properties were calculated using simulation software available online such as Molinspiration, Molsoft, Osiris Property Explorer, pkCSM, SwissADME, and GUSA. The results provided important information which allowed us to consider the evaluation of the antifungal activity of these novel compounds. Therefore, the antifungal activity of these compounds was evaluated in vitro against four filamentous fungi, including Aspergillus fumigatus ATCC 16907, Trichosporon cutaneum ATCC 28592, Rhizopus oryzae ATCC 10329, and Mucor hiemalis ATCC 8690; as well as six species of yeast from the Candida genus; C. albicans ATCC 10231, C. utilis ATCC 9226, C. tropicalis ATCC 13803, C. parapsilosis ATCC 22019, C. glabrata ATCC 34138 and C. krusei ATCC 14243 The sensibility studies suggest that compounds 1b, 2a and 2b can be considered  candidates for complementary biological studies due to the exhibited antifungal activity.   Resumen. La familia de compuestos conocidos como azoles forman parte de la mayoría de los medicamentos utilizados para el tratamiento de infecciones. Dentro de este grupo, los triazoles han sido extensamente estudiados como farmacóforos con resultados muy prometedores. En este trabajo, se sintetizaron cuatro nuevos 1,2,3-triazoles trisustituidos, que incluyen un anillo de tienopiridina en su estructura (1a,b; 2a,b) a través de una cicloadición 1,3-dipolar del tipo azida-enolato. Sus propiedades quimio informáticas fueron calculadas utilizando programas de simulación encontrados en línea como Molinspiration, Molsoft, Osiris Property Explorer, pkCSM, SwissADME y GUSAR. Los resultados obtenidos presentaron información importante que permitió considerar la evaluación de la actividad antifúngica de estos nuevos compuestos. Por lo tanto, esta actividad fue evaluada in vitro en cuatro cepas de hogos filamentosos, incluyendo Aspergillus fumigatus ATCC 16907, Trichosporon cutaneum ATCC 28592, Rhizopus oryzae ATCC 10329, and Mucor hiemalis ATCC 8690, así como también seis especies de levaduras del género Candida; C. albicans ATCC 10231, C. utilis ATCC 9226, C. tropicalis ATCC 13803, C. parapsilosis ATCC 22019, C. glabrata ATCC 34138 and C. krusei ATCC 14243. En estos estudios se observó que los compuestos 1a, 2a, y 2b pueden ser considerados para estudios posteriores de la evaluación biológica debido a la inhibición observada.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"14 2","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139126383","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"4(S)-Benzyl-1,3-thiazolidin-2-one a Novel Chiral Auxiliary for Asymmetric Aldol Coupling through Titanium Enolates","authors":"Dulce M. Mejia-Nuñez, Salvador Mastachi-Loza, Diego Martínez-Otero, M. Romero-Ortega","doi":"10.29356/jmcs.v68i1.2067","DOIUrl":"https://doi.org/10.29356/jmcs.v68i1.2067","url":null,"abstract":"The chlorotitanium enolate of N-propionyl-4(S)-benzyl-1,3-thiazolidin-2-one, was condensed with aryl aldehydes, in good diastereoselectivity to give the ‘Evans syn’ aldol (73:27 - 97:3), using equimolar amounts of titanium tetrachloride (1.5 equiv), and N,N-diisopropylethylamine (DIPEA). The facial selectivity in the aldol additions probably involves a non-chelated transition state. In all aldol reactions, the presence of a minor product, the ‘non-Evans syn’ aldol, was obtained and confirmed by X-ray diffraction analysis of a single-crystal compound containing the mixture of diastereoisomers. The chiral auxiliary in these 1,3-thiazolidin-2-one aldol derivatives can be easily removed by nucleophilic species through acyl substitution.   Resumen. El enolato de clorotitanio de N-propionil-4(S)-bencil-1,3-tiazolidin-2-ona, fue condensado con arilaldehídos, con buena diastereoselectividad produciendo el aldol “syn Evans” (73:27 - 97:3), utilizando cantidades equimolares de tetracloruro de titanio (1.5 equiv) y N,N-diisopropiletilamina (DIPEA). La selectividad facial en las adiciones aldólicas probablemente implica un estado de transición no-quelatado. En todas las reacciones aldólicas, la presencia de un producto minoritario, él aldol “non-Evans”, fue obtenido y confirmado por el análisis de difracción de rayos-X de monocristal de una mezcla de los diastereoisómeros. El auxiliar quiral en estos derivados de 1,3-tiazolidin-2-onas puede ser removido fácilmente por especies nucleofílicas a través de la sustitución del grupo acilo.","PeriodicalId":17377,"journal":{"name":"Journal of the Mexican Chemical Society","volume":"28 16","pages":""},"PeriodicalIF":1.5,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139129531","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}