Recent Advances in (Di)Azafluorene Chemistry (A Review) DOI
Е. Б. Рахимова, Victor Yu. Kirsanov

Russian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 60(11), P. 2086 - 2107

Published: Nov. 1, 2024

Language: Английский

Enantioselective Synthesis of Tetrahydro-1H-1,3-methanocarbazoles by Formal (3 + 3)-Cycloaddition Using Bicyclo[1.1.0]butanes DOI
Shubham Dutta, Constantin G. Daniliuc, Christian Mück‐Lichtenfeld

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Asymmetric synthesis presents many challenges, with the selective formation of chiral bridged polyheterocycles being a notable example. Cycloadditions using bicyclo[1.1.0]butanes (BCB) offer promising solution along those lines, yet, despite significant advances in that emerging area, asymmetric control has remained limited thus far. Here, we describe an organocatalytic, enantioselective formal (3 + 3)-cycloaddition BCBs 1H-indol-3-yl((hetero)aryl)methanol derivatives. This approach enables rapid and efficient tetrahydro-1H-1,3-methanocarbazole derivatives (34 examples) from readily available starting materials, very good stereochemical (up to 98:2 er). Successful scale-up experiments product modification demonstrated potential this methodology. Control DFT calculations provide insights into mechanistic pathway.

Language: Английский

Citations

2
Copper-Catalyzed Intermolecular [2 + 2 + 2] Annulation of Diynes with Alkynes: Construction of Carbazoles DOI
Zhentao Zhang,

Chen Luo,

Zhiyong Yu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Transition-metal-catalyzed [2 + 2 2] annulation of alkynes is an efficient pathway for the synthesis aromatic compounds. However, most established methods require noble metal catalysts. Herein, we report a copper-catalyzed intermolecular diynes with through vinyl cation intermediates, enabling atom-economical preparation biologically important carbazole skeletons. The reaction shows good regioselectivity in aryl(alkyl)alkynes. Moreover, preliminary results have also been obtained related catalytic atroposelective transformation. This represents rare example non-noble-metal-catalyzed ynamides pathway.

Language: Английский

Citations

1
Benzannulation of Functionally Enhanced Indole-3-carbaldehydes with Ynones and Alkynoates: A Domino Approach to Bioactive Carbazoles─Synthesis of Clauolenzole A, Calothrixin A & B, Methyl Carbazole-3-carboxylate, and Quinocarbazole DOI
Shweta Singh,

Rahul Balu Dadhe,

Srihari Pabbaraja

et al.

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

Published: Feb. 5, 2025

A flexible, regioselective, benzannulation strategy toward multifunctional carbazoles from 2-(2-oxo-2-arylethyl)indole-3-carbaldehydes, employing either ynones or alkynoates as reaction partners, has been envisaged and implemented. This enabling access to variegated in one-flask operation leads strategic substituent diversification via partner variation. The efficacy applications of this methodology are demonstrated through 23 examples concise syntheses bioactive clauolenzole A, calothrixin & B, methyl carbazole-3-carboxylate, pharmacophoric quinocarbazole.

Language: Английский

Citations

1
Analysis of skeletal diversity of multi-target directed ligands (MTDLs) targeting Alzheimer’s disease DOI Creative Commons

Uzma Azam,

Muhammad Moazzam Naseer, Christophe Rochais

et al.

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 286, P. 117277 - 117277

Published: Jan. 18, 2025

Language: Английский

Citations

0
Biosynthesis of a N-Acetylated Tricyclic Carbazole with Antithrombotic Activity DOI

Jiaming Luo,

Yaoyao Shen, Peng Liu

et al.

Journal of Natural Products, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Tricyclic carbazoles are significant pharmacophores. Herein, heterologous expression of the carbazole-3,4-quinone (1) biosynthetic pathway in chassis host Streptomyces albus J1074 yielded a previously chemosynthesized orthoquinone carbazole (2) and three new N-acetylated (3-5). Their structures were established by combination HR-ESI-MS, NMR, X-ray crystallographic analysis. Compound 2, deaminated precursor 4 5, was enzymatically synthesized, indicating substrate tolerance key enzymes bacterial tricyclic-carbazole pathway. Mutagenetic analysis revealed an arylamine N-acetyltransferase homologous gene required for production compounds 3-5. Bioactivity using zebrafish model demonstrated that compound 5 has antithrombotic activity, potentially downregulating genes involved platelet activation coagulation cascade. These findings expand natural strategies structural diversification tricyclic alkaloids.

Language: Английский

Citations

0
Ionic Liquid-Assisted Approaches in the Synthesis of Nitrogen-Containing Heterocycles: A Focus on 3- to 6-Membered Rings DOI Creative Commons

P. K. Maity,

Amrit Krishna Mitra

Journal of Ionic Liquids, Journal Year: 2025, Volume and Issue: unknown, P. 100146 - 100146

Published: March 1, 2025

Language: Английский

Citations

0
The neuroprotective potential of carbazole in traumatic brain injury DOI

Akashdeep Singh Pathania,

Kavita Badhai,

Nirmal Singh

et al.

Brain Injury, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 11

Published: Dec. 18, 2024

Objective To review the neuroprotective potential of carbazole and its derivatives in management traumatic brain injury (TBI), focusing on their mechanisms action, preclinical findings, clinical applications.

Language: Английский

Citations

2
Recent Advances in (Di)Azafluorene Chemistry (A Review) DOI
Е. Б. Рахимова, Victor Yu. Kirsanov

Russian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 60(11), P. 2086 - 2107

Published: Nov. 1, 2024

Language: Английский

Citations

0