The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols

Satkar, Yuvraj; Wróbel, Kazimierz; Trujillo‐González, Daniel E.; Ortiz-Alvarado, Rafael; Jiménez‐Halla, J. Óscar C.; Solorio‐Alvarado, César R.

doi:10.3389/fchem.2020.563470

Cited by 14 publications

(7 citation statements)

References 63 publications

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“…[4] Concerning this research, nitrogen-containing compounds, specifically those with the indole core, are among the most important group of heterocycles which are present in hundreds of pharmacological active drugs and treatments. [5][6][7][8][9][10][11] Synthetic methods for accessing to this class of active compounds involves in general, the use of metal free [12][13][14][15][16][17][18][19][20][21][22][23][24] or metal catalyzed [25,26] strategies. In the context of this work, we referred to indomethacin, as an indole-containing drug, considered one of the most efficient anti-inflammatories which acts as nonselective COX-1 and COX-2 inhibitor.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐inflammatory Effect of Simple 2,3‐Diarylindoles. On Route to New NSAID Scaffolds

Segura‐Quezada,

Alba‐Betancourt,

Chacón‐García

et al. 2024

ChemistrySelect

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

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐inflammatory Effect of Simple 2,3‐Diarylindoles. On Route to New NSAID Scaffolds

Segura‐Quezada,

Alba‐Betancourt,

Chacón‐García

et al. 2024

ChemistrySelect

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“…Organic chemistry is, among the scientific disciplines, the most used tool to obtain treatments for clinical and/or biological affections. This discipline has been evolving with time, increasing the development of compounds with high pharmaceutical interest, using strategies such as metal-catalyzed, [1,2] metalfree [3][4][5][6][7][8][9][10] or natural occurring compounds synthesis and derivatization. [11][12][13] These compounds have been developed with specific goals, such as for the treatment of cancer, [14,15] mycoses, [16] polycystic ovarian, pain, inflammation [17] hyper-glycemia and lastly but not less important: diabetes mellitus.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin vivoEvaluation of Fluorobenzyl Metformin Derivatives as Potential Drugs in The Diabetes Treatment

Hernández‐Velázquez,

Herrera,

Alba‐Betancourt

et al. 2023

Asian J Org Chem

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

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“…One of the most important tools which has played a key role in the development of the aforementioned treatments is organic synthesis . This important contributor to science takes advantage of the knowledge from different strategies and concepts which involve the use of transition metals [7–8] as well as metal‐free protocols [9–16] . Also important is the design and synthesis of different active compounds for addressing other affections such as pain [17] or inflammation [18] .…”

Section: Introductionmentioning

confidence: 99%

“…This important contributor to science takes advantage of the knowledge from different strategies and concepts which involve the use of transition metals [7][8] as well as metal-free protocols. [9][10][11][12][13][14][15][16] Also important is the design and synthesis of different active compounds for addressing other affections such as pain [17] or inflammation. [18] In this context one of the most important (NSAID) non-steroidal anti-inflammatory drug with historical importance due to its effectivity is indomethacin.…”

Section: Introductionmentioning

confidence: 99%

Indomethacin Synthesis, Historical Overview of Their Structural Modifications

et al. 2022

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One of the most important (NSAID) non-steroidal anti-inflammatory drug-containing the indol core is represented by the indomethacin. This highly relevant compound has been used for the last 50 years with excellent pharmacological results. Due to its relevant efficacy as an anti-inflammatory treatment, several syntheses have been developed during this half of century. Herein is summarized and discussed the most representative strategies which successfully addressed the total syntheses of indomethacin as well as some of its derivatives generated by carrying out strategic modifications at the nitrogen atom, the carboxylic acid at C-3, the methoxy group at C-5 and the methyl group at C-2.[a] K.

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The Diaryliodonium(III) Salts Reaction With Free-Radicals Enables One-Pot Double Arylation of Naphthols

Cited by 14 publications

References 63 publications

Synthesis and Anti‐inflammatory Effect of Simple 2,3‐Diarylindoles. On Route to New NSAID Scaffolds

Synthesis and Anti‐inflammatory Effect of Simple 2,3‐Diarylindoles. On Route to New NSAID Scaffolds

Synthesis andin vivoEvaluation of Fluorobenzyl Metformin Derivatives as Potential Drugs in The Diabetes Treatment

Indomethacin Synthesis, Historical Overview of Their Structural Modifications

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