Multidrug Resistance Reversed by Maleimide Interactions. A Biological and Synthetic Overview for an Emerging Field DOI
Edson D. Hernández‐Velázquez, Angélica Judith Granados‐López, Jesús Adrián López

et al.

ChemBioChem, Journal Year: 2024, Volume and Issue: 26(1)

Published: Oct. 9, 2024

Abstract Multidrug Resistance (MDR) can be considered one of the most frightening adaptation types in bacteria, fungi, protozoa, and eukaryotic cells. It allows organisms to survive attack many drugs used daily basis. This forces development new more complex, highly specific fight diseases. Given high usage medicaments, poor variation active chemical cores, self‐medication, appearance MDR is frequent each time, has been established as a serious medical social problem. Over years it possible identification several genes proteins responsible for with that blockers them reach reversion try avoid global These mechanisms also have observed cancer cells, calcium channel successful reversion, maleimide found included them. In this review, we explore particularly tree main involved chemoresistance, MRP1 (encoded by ABCC1), BCRP ABCG2) P‐gp ABCB1). The participation remarkably important, aspects its regulations are discussed. Additionally, address history, mechanisms, efforts, specifically focused on synthesis MDR‐reversers co‐administration, well how their biological applications imperative expand available information very plausible source.

Language: Английский

Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents DOI Creative Commons
Akira Yoshimura, Viktor V. Zhdankin

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

Citations

27
Synthesis and Anti‐inflammatory Effect of Simple 2,3‐Diarylindoles. On Route to New NSAID Scaffolds DOI
Luis A. Segura‐Quezada, Clara Alba Betancourt, Luis Chacón‐García

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(4)

Published: Jan. 22, 2024

Abstract Nitrogen‐containing drugs represent one of the worldwide most extensive sources treatments for different diseases. Indomethacin as example, is important non‐steroidal anti‐inflammatories (NSAID) indol‐containing drug. Its relevance has been demonstrated last 50 years with excellent pharmacological results. efficacy an anti‐inflammatory treatment, inspired us exploration structurally less elaborated compounds which kept and/or improve activity compared indomethacin. Herein summarized and discussed our initial findings on synthesis effect 2,3‐diarylindoles, designed strategically favoring plausible selective interactions COX‐2, route to new simple NSAID scaffolds. The TPA model formalin test were used in this study generate inflammation mice conducting assays synthesized 2,3‐diarylindoles. Docking analysis revealed stronger N−H indolic COX‐2 6‐methoxy‐2‐phenyl‐3‐(4‐chlorophenyl)‐1 H ‐indole, active when This, experimentally match observed putatively indicates biochemical action mechanism.

Language: Английский

Citations

4
Iodine(III)-Containing Reagents in Photo-Assisted and Photo-Catalyzed Organic Synthesis DOI Creative Commons
Jaime G. Ibarra‐Gutiérrez, Luis A. Segura‐Quezada, Edson D. Hernández‐Velázquez

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(4), P. 784 - 784

Published: Feb. 8, 2025

Iodine(III) reagents have become a highly relevant tool in organic synthesis due to their great versatility as strong but green oxidants. Several transformations involving cyclizations well functionalization of different cores been broadly described and reviewed. Herein, the participation these photochemical exclusively by direct irradition or photoredox cycles using some transition metals, will be briefly plausible further that potentially can developed.

Language: Английский

Citations

0
Activation of I2 with Aryl Iodine(III) for the Iodination of Deactivated Arenes DOI
Marcus Sceney, Jun‐Ho Choi,

Lachlan Barwise

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

A method for iodinating deactivated aryl rings is reported using a greatly reduced quantity of H2SO4 (<1 vol %) compared with traditional methods, which often requires it as bulk solvent. new iodine(III) system oxidizes I2 in organic solvents (CH2Cl2, CHCl3) trifluoroacetic anhydride water scavenger. Catalytic used the case highly rings. The oxidants 4-nitrophenyliodine bis(trifluoroacetate) (NPIFA), 3-iodosylbenzoic acid (3-IBA), and 2,4-dichloro-5-iodosylbenzoic (3-IBACl2) are applied based on separability reactivity target substrates, their forms recovered by simple acid/base extractions, demonstrating excellent reusability. Leveraging this, iodinated products isolated without need chromatography. suitable use under benchtop conditions exhibits high efficiency iodine oxidant, well positional selectivity substrates tested.

Language: Английский

Citations

0
Synthesis and Biological Evaluation of Strong Cytotoxic Maleimide Derivatives with Potential Multidrug Resistance Reversal Activity in the Breast Cancer Therapy DOI
Edson D. Hernández‐Velázquez, Angélica Judith Granados‐López,

Jorge Gustavo Araujo-Huitrado

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(13)

Published: April 1, 2025

Abstract Maleimide core is a broadly used chemical‐based scaffold for natural and new compounds synthesis. Several of them show anticancer multidrug resistance (MDR) reversal activity. A family twelve 3,4‐substituted N ‐benzyl ‐methyl maleimides were synthesized in two‐step sequence consisting bromination Suzuki cross‐coupling or bromination–thiolation. We able to obtain two groups maleimide derivatives which tested determining their cytotoxicity. Following our previous work, the biological activity these as MDR agents was with cancerous cell line MCF‐7 that has been exposed chronically etoposide achieve MDR. resistant (MCF‐7R), treated combination synthetized compounds. The results presented strong effects 20 , 21 22 23 24, 25 no cells, IC 50 values proliferation inhibition ranged from 1.8–30.8 µM. between shows increase most except compound 15 where it shown low reversion degree. These findings suggest this work can be tumorigenic cancer cells before after acquiring resistance. should evaluated considering an undesirable effect caused due increase.

Language: Английский

Citations

0
Divergent role of PIDA and PIFA in the AlX3 (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study DOI Creative Commons
Kevin A. Juárez‐Ornelas, Manuel Solís-Hernández, Pedro Navarro‐Santos

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1580 - 1589

Published: July 15, 2024

The reaction mechanism for the chlorination and bromination of 2-naphthol with PIDA or PIFA AlX

Language: Английский

Citations

3
Synthesis andin vivoEvaluation of Fluorobenzyl Metformin Derivatives as Potential Drugs in The Diabetes Treatment DOI
Edson D. Hernández‐Velázquez, Mayra Denise Herrera, Clara Alba Betancourt

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(7)

Published: May 23, 2023

Abstract Metformin is a versatile, biocompatible, and cheap bis‐guanidine used as first response line in the type II diabetes treatment. Since its human trials (1956) several structural modifications were carried out to increase activity. However, with this augmented activity, biological compatibility diminishes, generating serious side effects, such lactic acidosis. Considering that cytochrome P450 oversees metformin metabolism weakness eliminate fluorinated metabolites; we envisioned synthesis of benzyl derivatives. In our hypothesis fluorine atoms can give, by inductive effect, higher acidity hydrogen benzylic nitrogen, increasing solubility. On other hand, would give resistance cP450 allowing molecule acting longer. Thus, family fourteen fluorobenzyl metformins synthesized characterized, then an vitro enzymatic assay α‐amylase was performed select five best performing compounds, vivo experiment streptozotocin‐induced CD1 mice using selected Blood glucose measured every day. After sacrifice, lipid profile, serum, liver γ‐glutamyl transferase (GGT) activity determined biocompatibility. Results showed two compounds ( 1 L M ) enhanced biocompatibility for blood glucose, lipids GGT regulation.

Language: Английский

Citations

8
K2S2O8-Promoted Consecutive Tandem Cyclization/Oxidative Halogenation: Access to 3-Halo-Pyrazolo[1,5-a]pyrimidines DOI Creative Commons
Papiya Sikdar,

Tathagata Choudhuri,

Suvam Paul

et al.

ACS Omega, Journal Year: 2023, Volume and Issue: 8(26), P. 23851 - 23859

Published: June 22, 2023

A one-pot methodology has been developed to synthesize 3-halo-pyrazolo[1,5-a]pyrimidine derivatives through the three-component reaction of amino pyrazoles, enaminones (or chalcone), and sodium halides. The use easily accessible 1,3-biselectrophilic reagents like chalcone offers a straightforward approach for synthesis 3-halo-pyrazolo[1,5-a]pyrimidines. proceeded cyclocondensation between pyrazoles with enaminones/chalcone in presence K2S2O8 followed by oxidative halogenations NaX-K2S2O8. Mild environmentally benign conditions, wide functional group tolerance, scalability are attractive facet this protocol. combination NaX-K2S2O8 is also beneficial direct pyrazolo[1,5-a]pyrimidines water.

Language: Английский

Citations

8
Trifluoromethylarylation of alkenes using anilines DOI Creative Commons
Carlos Corral Suarez, Ignacio Colomer

Chemical Science, Journal Year: 2023, Volume and Issue: 14(43), P. 12083 - 12090

Published: Jan. 1, 2023

Nitrogen containing compounds, such as anilines, are some of the most widespread and useful chemical species, although their high unselective reactivity has prevented incorporation into many interesting transformations, functionalization alkenes. Herein we report a method that allows trifluoromethylarylation alkenes using for first time, with no need additives, transition metals, photocatalysts or an excess reagents. An in-depth mechanistic study reveals key role hexafluoroisopropanol (HFIP) unique solvent, establishing hydrogen bonding network aniline trifluoromethyl reagent, is responsible altered exquisite selectivity. This work uncovers new mode involves use abundant anilines non-prefunctionalized aromatic source simultaneous activation hypervalent iodine reagent.

Language: Английский

Citations

7
Understanding the Regiodivergence between Hydroarylation and Trifluoromethylarylation of 1,3-Dienes Using Anilines in HFIP DOI Creative Commons
Carlos Corral Suarez, Israel Fernández, Ignacio Colomer

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(5), P. 1744 - 1751

Published: May 10, 2024

Conjugated dienes (1,3-dienes) are versatile and valuable chemical feedstocks that can be used as two-carbon or four-carbon synthons with vast applications across the industry. However, main challenge for their productive incorporation in synthetic routes is chemo-, regio-, stereoselective functionalization. Herein, we introduce a unified strategy 1,2-hydroarylation 1,4-trifluoromethylarylation of 1,3-dienes using anilines hexafluoroisopropanol. DFT calculations point toward kinetically controlled process both transformations, particularly trifluoromethylarylation, to explain regiodivergent outcome. In addition, perform an extensive program functionalization diversification products obtained, including hydrogenation, oxidation, cyclizations, cross-coupling reactions, allows access library high-value species straightforward manner.

Language: Английский

Citations

2