Metformin, a biological and synthetic overview

Bioorganic & Medicinal Chemistry Letters, Год журнала: 2023, Номер 86, С. 129241 - 129241

Опубликована: Март 16, 2023

Язык: Английский

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

ChemistrySelect, Год журнала: 2024, Номер 9(4)

Опубликована: Янв. 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.

Язык: Английский

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Iodine(III)-Containing Reagents in Photo-Assisted and Photo-Catalyzed Organic Synthesis

Molecules, Год журнала: 2025, Номер 30(4), С. 784 - 784

Опубликована: Фев. 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.

Язык: Английский

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Synthesis, Formation Mechanisms, and Molecular Dynamics Simulation of Novel Benzothiazole and Benzo[1,4]oxazin-3(4H)-one as Potential Acetylcholinesterase Inhibitors

ACS Omega, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

A novel series of benzothiazole derivatives was synthesized using straightforward and easily implementable procedures, achieving a high yield. Among these compounds, amino acids containing the moiety were successfully produced through an 8-step process, with yields reaching as 95%. Notably, serendipitous compound both benzo[1,4]oxazin-3(4H)-one moieties also same protocol, bypassing purification at step 7 proceeding directly to hydrolysis. This highlights unique role coupling reagent HATU (hexafluorophosphate azabenzotriazole tetramethyluronium) in reaction, it facilitated yields, up 90%. The structures newly compounds confirmed spectral analysis. Density functional theory calculations suggested that energy barriers can be overcome by utilizing from exothermic enabling thermodynamically favorable formation this structure. Compounds 6d 6f demonstrated significant inhibitory activity against enzyme acetylcholinesterase, IC50 values 32.00 25.33 μg/mL, respectively. Molecular docking molecular dynamics analyses indicate hold potential for combating Alzheimer's disease, due their interactions critical acid residues structural stability.

Язык: Английский

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Synthesis and Biological Evaluation of Strong Cytotoxic Maleimide Derivatives with Potential Multidrug Resistance Reversal Activity in the Breast Cancer Therapy

ChemistrySelect, Год журнала: 2025, Номер 10(13)

Опубликована: Апрель 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.

Язык: Английский

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Iodine(III)‐Mediated Free‐Aniline Iodination through Acetyl Hypoiodite Formation: Study of the Reaction Pathway

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(45)

Опубликована: Ноя. 15, 2022

Abstract The first iodine(III)‐mediated para ‐selective iodination protocol for free anilines as well the mechanistic elucidation of reaction pathway is described. developed method proceeded under clean, non‐toxic, efficient, and in general mild conditions. To best our knowledge this report describes time a procedure focused specifically on introduction an iodine atom using PIDA [(diacetoxyiodo)benzene] ammonium iodide which formed situ acetyl hypoiodite (AcO‐ I ) halogenating species. Our DFT calculations suggest mechanism that highlights catalytic role cation AcO‐ formation halogenation. Considering there are few procedures non‐acidic conditions, herein we described initial operationally simple alternative iodine(III) reagents.

Язык: Английский

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1,3‐Oxazine as a Promising Scaffold for the Development of Biologically Active Lead Molecules

ChemistrySelect, Год журнала: 2023, Номер 8(39)

Опубликована: Окт. 15, 2023

Abstract Heterocyclic compounds form an important part of wide range biologically active molecules. The heteroatom provides them specificity for various receptors. 1,3‐oxazine has been considered as a privileged scaffold in many medicinal chemistry applications. Compounds having moiety exhibit broad biological applications such anticancer, antimicrobial, anti‐inflammatory, antiplatelet, antitubercular and alpha‐glucosidase inhibition activities. In this review, we consolidate the recent developments synthesis activities containing compounds. Also, structure activity relationship (SAR) studies different derivatives exhibiting several are summarized. Database Science direct, Pubmed Google scholar were searched using keywords ‘1,3‐Oxazine’, ‘synthesis’, ‘derivatives’, ‘biological activities’. review would provide lead development competent candidates with treatment human disorders.

Язык: Английский

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Divergent role of PIDA and PIFA in the AlX₃ (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1580 - 1589

Опубликована: Июль 15, 2024

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

Язык: Английский

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

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(7)

Опубликована: Май 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.

Язык: Английский

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Iodine(III)‐Mediated Electrophilic Chlorination and Catalytic Nitration of N‐Tosyl Anilines

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(47)

Опубликована: Ноя. 22, 2022

Abstract An efficient iodine(III)‐based protocol for the chlorination and catalytic nitration of N ‐tosyl anilines as well proposed reaction mechanism is described. The synergistic combination commercially available [bis(trifluoroacetoxy)iodo]benzene (PIFA) with AlCl 3 , or (PhIO) n Al(NO ) allowed electrophilic introduction chlorine nitro group in aniline core non‐acidic conditions. Our DFT calculations, performed process, indicate that this occurs through a cationic pathway which [Cl‐PhI OTFA⋅AlCl ] chlorinating species formed under neutral

Язык: Английский

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