Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(2), P. 162 - 164

Published: Jan. 1, 2025

Language: Английский

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Peptide‐Triazolobenzodiazepine Hybrids: A Catalyst‐Free on‐Resin Strategy to Build Complex Therapeutic Motifs Into Peptides

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: April 16, 2025

Abstract The merger of peptide and heterocyclic chemistry presents significant opportunities for enhancing the structural functional diversity therapeutic agents. In this study, we introduce a streamlined on‐resin method to modify peptides at N ‐terminus amines side chain Lys/Orn amino acids by incorporating biologically active triazolobenzodiazepine scaffold. presented solid‐phase synthesis (SPPS), core is formed through combination ‐alkylation, amide bond formation, an alkyne‐azide 1,3‐dipolar cycloaddition, which latter two happen as single‐step one‐pot reaction‐ proceeding under mild conditions without metal catalysts. This protocol tolerates wide variety groups, providing versatile synthesizing peptide‐triazolobenzodiazepine hybrids. Using orthogonal protection group strategies, further demonstrate method's adaptability site modifications in involving both Lys amines. These enhance scope “peptide medicinal chemistry” creating multifunctional with potential applications. compatibility SPPS, room temperature conditions, elimination catalysis make it efficient powerful tool modification.

Language: Английский

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In Situ Generation of Fluorescent Amino Acids and Peptides via Double C–H Activation/Annulation

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(20), P. 13569 - 13576

Published: Oct. 6, 2023

Unnatural fluorescent amino acids have been synthesized to obtain better emission wavelengths, fluorescence lifetime, and quantum yields. Despite major advances, most of them face inherent restrictions as fluorophores are limited the methods from coupling between fluorophores. Herein, we develop a Rh(III)-catalyzed double C–H activation/annulation reaction diverse benzamides with alkynes for synthesis tricyclic-fused aromatic hydrocarbon carbocations. The robustness this strategy is demonstrated by diversification Lys-based peptides, in situ generating tricyclic This method features broad substrate scope high atom step economy well chemo- site selectivity. Unsymmetrical employing two different tolerated produce unnatural These display tunable emission, low cytotoxicity, potential specifically targeting lysosomes.

Language: Английский

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Palladium(II)-Catalyzed Site-Selective C(sp³)–H Alkenylation of Oligopeptides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9455 - 9459

Published: Oct. 24, 2024

An innovative palladium-catalyzed alkenylation of peptides and vinyl iodides has been developed. This method does not require the introduction a directing group uses carboxylic acid groups as endogenous groups. It is noteworthy that two key building blocks for ilamycins CXCR7 modulators were prepared using our methodology. In addition, free residue can be linked to variety other compounds, providing novel approach synthesis peptide drugs in future.

Language: Английский

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Rh(III)-Catalyzed Double C–H Activation toward Peptide–Benzazepine Conjugates

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

We herein report the efficient synthesis of peptide–benzazepine conjugates from Lys-based peptides and acroleins via Rh(III)-catalyzed double C–H activation. This reaction features mild conditions, broad scope, high atom step economies, excellent chemo- site selectivity. The synthetic utility this strategy is further demonstrated by scale-up experiments product derivatizations, including diverse late-stage ligations based on aldehyde moiety. preliminary biological activity studies show that have good antifungal activities toward crop forest pathogenic fungi.

Language: Английский

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Metal‐Free Bicyclization for the Construction of N−O Fused Tetracyclic Isoquinolones

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

Published: Oct. 9, 2023

Abstract A hypervalent iodine‐mediated bicyclization of N‐alkoxybenzamides for the synthesis polyheterocycles is reported. Through metal‐free strategy, various N−O fused tetracyclic isoquinolones are synthesized in moderate to good yields at room temperature. The show fluorescent properties, with maximum emission wavelength ranging from 442 459 nm. Notably, preliminary antifungal activity investigations indicate that activities towards crop and forest pathogenic fungi. One them exhibits 75.9 % C. chrysosperma , which much better than positive control.

Language: Английский

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Ru(II)-Catalyzed C(sp²)–H Activation Annulation: Synthesis of Fluorescent Benzoisoquinolonyl Acetate/Peptides from N-Arylamides and Ethyne at Room Temperature

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7485 - 7494

Published: May 15, 2024

Benzoisoquinolones are aryl ring extended isoquinolinone derivatives, which constituents of alkaloid natural products. This report describes the synthesis novel benzoisoquinolone amino acid/peptide derivatives from respective

Language: Английский

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Heterogeneous visible-light photoredox catalysis with NiCl2@g-C3N4 for induced C(sp2)-H/N H cross-dehydrogenative coupling

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 569, P. 114633 - 114633

Published: Oct. 25, 2024

Language: Английский

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Triple C–H Activation/Annulation: In Situ Construction of Fluorescent Peptides

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

Herein, we report a Rh(III)-catalyzed triple C-H activation-annulation of Phe-based peptides with alkynes for the preparation fluorescent peptides. The robustness this protocol is reflected by broad substrate scope, high atom- and step-economy, excellent chemo- site-selectivity. An in situ generated polycyclic aromatic hydrocarbon carbocation as fluorophore exhibits good fluorescence properties (maximum emission wavelength up to 628 nm) low cell cytotoxicity. synthetic utility method further demonstrated versatile product applications bioconjugation protein BSA specifically targeting lysosomes mitochondria live mammalian cells.

Language: Английский

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Ru(II)-Catalyzed C(sp2)–H Activation Annulation: Synthesis of Fluorescent Benzoisoquinolonyl Acetate/Peptides from N-Arylamides and Ethyne at Room Temperature

Published: Dec. 20, 2023

Benzoisoquinolones are aryl ring extended isoquinolinone derivatives, constituents of alkaloid natural products. This report describes the synthesis benzoisoquinolones amino acids/peptides derivatives from respective N-aryl esters /peptides through Ru-catalyzed C(sp2)–H annulation at room temperature. Herein, acid ester/amide residue acts as a directing group for ring, and then cyclization occurs amide NH. Importantly, these benzoisoquinolinones exhibit fluorescence in protic polar solvents. Hence, this methodology could be helpful to transform standard ac-ids/peptides into fluobenzoisoquinolinones conjugated fluorescent peptide temperature, which applicable leveling acid/peptides effectively.

Language: Английский

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