An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20 : 1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c8cc08275h | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Selective Synthesis of Tetrahydroisoquinoline and Piperidine Scaffolds by Oxidative Ring Opening/Ring Closing Protocols of Substituted Indenes and Cyclopentenes.
ChemistryOpen
December 2024
MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, HUN-REN Research Center for Natural Sciences, H-1117, Budapest, Magyar tudósok krt. 2, Hungary.
Novel tetrahydroisoquinoline and piperidine derivatives were selectively synthesized from substituted indenes or cyclopentenes. The process starts with an oxidative cleavage of the ring olefin bond, which gives reactive diformyl intermediates. By a ring-closing step using chiral (R) or (S) α-methylbenzylamine under a reductive amination protocol facilitated ring formation with ring expansion of the corresponding nitrogen-containing heterocycles.
View Article and Find Full Text PDFEnhanced Bioactivity of Quercetin-Tetrahydroisoquinoline Derivatives: Effect on Lipophilicity, Enzymes Inhibition, Antioxidant Potential, and Cytotoxicity.
Int J Mol Sci
December 2024
Vinča Institute of Nuclear Sciences, National Institute of the Republic of Serbia, University of Belgrade, P.O. Box 522, 11000 Belgrade, Serbia.
Quercetin, a well-known flavonoid with significant medicinal potential, was derivatized at the C8 position with a tetrahydroisoquinoline (THIQ) moiety, and physicochemical and pharmacological properties, inhibition potential, antioxidant activity, and cytotoxicity of new compounds were evaluated. Physicochemical and pharmacological properties, including lipophilicity, membrane permeability, and P-glycoprotein substrate affinity, were assessed theoretically using the SwissADME software. The metal-chelating ability of the new compounds was evaluated on metal ions Fe, Zn, and Cu, whose homeostasis disruption is linked to the development of Alzheimer's disease.
View Article and Find Full Text PDFSynthesis and characterization of metal dithiocarbamate derivatives of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline.
Sci Rep
November 2024
Department of Inorganic Chemistry, Shahid Beheshti University, Tehran, 19839 69411, Iran.
Five metal dithiocarbamate complexes [M(PTHIQDTC)] [where PTHIQDTC is (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline dithiocarbamate anion and M is Ni(II) (1), Sn(II) (2), Hg(II) (3), Pb(II) (4) and Zn(II) (5)] were synthesized from the reaction of MX (X is Cl for 1-3 and OAc for 4-5) with ligand of triethylammonium (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline dithiocarbamate [EtNH][PTHIQDTC] in methanolic solution at room temperature. The five complexes were characterized by IR, H andC NMR, mass spectrometry, elemental analysis and TGA analysis. Recrystallization of [Zn(PTHIQDTC)] (5) in dimethylsulfoxide (DMSO) converts 5 to [Zn(PTHIQDTC)(DMSO)] (6).
View Article and Find Full Text PDFNew 5, 6, 7, 8-Tetrahydro-Isoquinolines Bearing 2-Nitrophenyl Group Targeting RET Enzyme: Synthesis, Anticancer Activity, Apoptotic Induction and Cell Cycle Arrest.
Chem Biodivers
November 2024
Pharmacology Unit, Cancer Biology Department, National Cancer Institute, Cairo University, Cairo, Egypt.
Article Synopsis
- The study focused on synthesizing new compounds, specifically 5,6,7,8-tetrahydroisoquinolines and 6,7,8,9-tetrahydrothieno[2,3-c]isoquinolines, and confirmed their structures using various spectroscopic techniques.
- Anticancer activities of these new compounds were tested against eight tumor cell lines, revealing that compound 3 was most effective against the HEPG2 cell line and compound 9c against the HCT116 cell line.
- Further analysis showed that compound 3 induced significant apoptosis and cell cycle arrest in HEPG2 cells, while molecular docking studies indicated that compounds 3
Mechanism of efficacy of trabectedin against myxoid liposarcoma entails detachment of the FUS-DDIT3 transcription factor from its DNA binding sites.
J Exp Clin Cancer Res
November 2024
Department of Experimental Oncology, Istituto di Ricerche Farmacologiche Mario Negri IRCCS, Milan, Italy.
Background: The marine drug trabectedin has shown unusual effectiveness in the treatment of myxoid liposarcoma (MLPS), a liposarcoma characterized by the expression of the FUS-DDIT3 chimera. Trabectedin elicits a significant transcriptional response in MLPS resulting in cellular depletion and reactivation of adipogenesis. However, the role of the chimeric protein in the mechanism of action of the drug is not entirely understood.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!