Identification of 1,3,4-oxadiazolyl-containing β-carboline derivatives as novel α-glucosidase inhibitors with antidiabetic activity

European Journal of Medicinal Chemistry, Год журнала: 2023, Номер 261, С. 115795 - 115795

Опубликована: Сен. 7, 2023

Язык: Английский

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New β-carboline derivatives as potential α-glucosidase inhibitor: Synthesis and biological activity evaluation

Journal of Molecular Structure, Год журнала: 2023, Номер 1283, С. 135279 - 135279

Опубликована: Март 7, 2023

Язык: Английский

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Synthesis of Tetrahydro-β-carboline Derivatives under Electrochemical Conditions in Deep Eutectic Solvents

ACS Omega, Год журнала: 2024, Номер 9(12), С. 14198 - 14209

Опубликована: Март 14, 2024

In this work, a novel, green, and atom-efficient method for the synthesis of tetrahydro-β-carboline derivatives using electrochemistry (EC) in deep eutectic solvents (DESs) was reported. The EC reaction conditions were optimized to achieve highest yield. experimental design also perform two-step, one-pot reaction, thereby time, workup procedure, needed all reduced. new approach achieved our strategy as served decrease time eliminate use hazardous catalysts, lower energy required targeted compounds. On other side, DESs used situ electrolytes, noninflammable green solvents. scope investigated different aromatic aldehydes. Finally, scalability gram-scale that afforded product an excellent

Язык: Английский

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Recent Advances on the Synthesis and Application of Tetrahydro‐β‐Carbolines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(14), С. 3050 - 3084

Опубликована: Май 22, 2024

Abstract Tetrahydro‐ β ‐carbolines (TH Cs) also known as tryptolines serve important structural elements in natural products and pharmaceutical compounds, they are utilized drug discovery. They display diverse bioactivities, including anticancer, antifungal, antiparasitic, anti‐ischemic, anti‐inflammatory, other activities. Besides their pharmacological biological significance, these motifs extensively used the production of bioactive compounds. This review is intended to summarize recent advancements chemistry this compound class, synthesis applications organic synthetic intermediates molecules.

Язык: Английский

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Modular assembly of indole alkaloids enabled by multicomponent reaction

Nature Communications, Год журнала: 2023, Номер 14(1)

Опубликована: Авг. 9, 2023

Indole alkaloids are one of the largest alkaloid classes, proving valuable structural moiety in pharmaceuticals. Although methods for synthesis indole constantly explored, direct single-step these chemical entities with broad diversity remains a formidable challenge. Herein, we report modular assembly tetrahydrocarboline type from simple building blocks single step while showing compatibility medicinally relevant functionality. In this protocol, 2-alkylated or 3-alkylated indoles, formaldehyde, and amine hydrochlorides could undergo one-pot reaction to deliver γ-tetrahydrocarbolines β-tetrahydrocarbolines directly. A wide scope readily available starting materials is applicable process, numerous divergent tetrahydrocarbolines be achieved rapidly. The control deuterium-labelling conducted probe mechanism. And mechanistically, multicomponent relies on multiple alkylamination cascade wherein an unusual C(sp3)-C(sp3) connection was involved process. This method render rapid access pharmaceutically interesting compounds, greatly enlarge library accelerate lead compound optimization thus facilitating drug discovery.

Язык: Английский

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A multicomponent reaction for modular assembly of indole-fused heterocycles

Chemical Science, Год журнала: 2024, Номер 15(14), С. 5211 - 5217

Опубликована: Янв. 1, 2024

Indoles are privileged chemical entities in natural products and drug discovery. Indole-fused heterocycles, particularly seven-membered ones, have received increasing attention due to their distinctive characteristics wide spectrum of bioactivities. However, the synthetic access these compounds is highly limited. Herein, we report a unique multicomponent reaction (MCR) for modular assembly indole-fused heterocycles. In this process, indole, formaldehyde amino hydrochloride could assemble rapidly yield oxadiazepines, another addition sodium thiosulphate would furnish thiadiazepines. The biological evaluation disclosed promising anticancer activity compounds. Furthermore, MCR be applicable late-stage selective modifications peptides. Therefore, work provides powerful strategy indole functionalization valuable tool construction

Язык: Английский

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Antifungal Tetrahydrocarbazole Compound CAR-8 Induces Endoplasmic Reticulum Stress in Candida albicans

ACS Infectious Diseases, Год журнала: 2024, Номер 10(8), С. 2705 - 2716

Опубликована: Июль 11, 2024

The development of new effective antifungal agents is essential to combat fungal infections. Tetrahydrocarbazole has been exploited as a promising skeleton against various pathogenic microorganisms and used search for novel active compounds. In this study, library composed small tetrahydrocarbazole compounds was screened, potent agent, CAR-8, identified with minimum inhibitory concentration 2-4 μg/mL Candida albicans. CAR-8 showed strong fungicidal activities killed almost all C. albicans within 3 h at 16 μg/mL. At concentrations 2 8 μg/mL, significantly inhibited the formation hyphae biofilms. Moreover, 10 20 mg/kg reduced load improved survival in infection model invertebrate Galleria mellonella. Transcriptome analysis revealed significant changes expression genes associated protein processing endoplasmic reticulum (ER), ER-associated degradation, unfolded response (UPR), which suggested that treatment induced ER stress. resulted phenotypes similar tunicamycin, classical stress inducer. These included nonconventional splicing HAC1 mRNA, fragmented morphology ER, distribution GFP-Snc1 Saccharomyces cerevisiae, cell apoptosis probably caused by More importantly, disruption IRE1 or increased sensitivity confirming UPR signaling pathway critical resistance. Overall, our study identifies stress-induced compound will help discovery drugs.

Язык: Английский

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The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Photocatalytic Enantioselective Radical Cascade Multicomponent Minisci Reaction of β‐Carbolines Using Diazo Compounds as Radical Precursors

Advanced Science, Год журнала: 2024, Номер 11(25)

Опубликована: Апрель 19, 2024

Abstract Here, a photocatalytic asymmetric multicomponent cascade Minisci reaction of β‐carbolines with enamides and diazo compounds is reported, enabling an effective enantioselective radical C─H functionalization high yields enantioselectivity (up to 83% yield 95% ee). This protocol exhibits step economy, chemo‐/enantio‐selective control, good functional group tolerance, allowing access variety valuable chiral β‐carbolines. Notably, are suitable precursors in reactions. Moreover, the efficiency practicality this approach demonstrated by synthesis bioactive natural products.

Язык: Английский

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A Green Synthesis of Carbene‐Metal‐Amides (CMAs) and Carboline‐Derived CMAs with Potentin vitroandex vivoAnticancer Activity

ChemMedChem, Год журнала: 2022, Номер 17(13)

Опубликована: Март 21, 2022

Abstract The modularity and ease of synthesis carbene‐metal‐amide (CMA) complexes based on the coinage metals (Au, Ag, Cu) N‐heterocyclic carbenes (NHCs) as ancillary ligands pave way for expansion their applications beyond photochemistry catalysis. Herein, we further improve such compounds by circumventing use toxic organic solvents which were previously required purification, expand scope to include incorporating carbolines amido fragments. novel are screened both in vitro ex vivo , against several cancer cell lines high‐grade serous ovarian (HGSOC) tumoroids, respectively. Excellent cytotoxicity values obtained most complexes, while structural variety CMA library thus far, provides promising leads future developments. Variations all three components (NHC, metal, ligand), enable establishment trends regarding selectivity towards cancerous over normal cells.

Язык: Английский

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