Synthesis of 5,6-Dihydropyrazolo[5,1-]isoquinolines through Tandem Reaction of ,-Cyclic Azomethine Imines with α,β-Unsaturated Ketones.

Molecules

Department of Chemistry, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Republic of Korea.

Published: April 2023

An innovative and efficient approach has been developed for the synthesis of 5,6-dihydropyrazolo[5,1-]isoquinolines. This one-pot tandem reaction involves the reaction of ,-cyclic azomethine imines with α,β-unsaturated ketones, using KCO as the base and DDQ as the oxidant. The process results in functionalized 5,6-dihydropyrazolo[5,1-]isoquinolines with good yields. This convenient one-step method encompasses a tandem [3 + 2]-cycloaddition, detosylation, and oxidative aromatization.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10180063PMC
http://dx.doi.org/10.3390/molecules28093710DOI Listing

Publication Analysis

Top Keywords

synthesis 56-dihydropyrazolo[51-]isoquinolines
8
tandem reaction
8
reaction -cyclic
8
-cyclic azomethine
8
azomethine imines
8
imines αβ-unsaturated
8
αβ-unsaturated ketones
8
56-dihydropyrazolo[51-]isoquinolines tandem
4
ketones innovative
4
innovative efficient
4

Similar Publications

Analysis of growth physiological changes and metabolome of highland barley seedlings under cadmium (II) stress.

Environ Pollut

January 2025

Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Sichuan Engineering & Technology Research Center of Coarse Cereal Industrialization, School of Food and Biological Engineering, Chengdu University, Chengdu, Sichuan, China. Electronic address:

This study aims to investigate the physiological changes in growth and metabolic response mechanisms of highland barley under different concentrations of cadmium. To achieve this, cadmium stress was applied to green barley at levels of 20, 40, and 80 mg/L. The results revealed that, under Cd(II) stress, the chlorophyll content and photosynthesis in leaves of highland barley seedlings were inhibited to some extent.

View Article and Find Full Text PDF

Background: Chemical derivatization is a common technique in liquid chromatography-mass spectrometry (LC-MS) metabolomics used to improve the ionizability and chromatographic properties of metabolites in complex biological samples. This process facilitates better detection and separation of a wide array of compounds. The reagent 2-(4-boronobenzyl) isoquinolin-2-ium bromide (BBII), developed as a glucose labeling reagent for matrix-assisted laser desorption/ionization MS, enhances ionization for glucose and other hydroxyl metabolites.

View Article and Find Full Text PDF

Berberine (BBR), an isoquinoline alkaloid abundant in Coptis chinensis, exhibits anti-tumor and hypoglycemic properties. The regulation of tumor cell homeostasis and metabolism is greatly influenced by Hypoxia-inducible factor-1α (HIF-1α). This research aims to elucidate whether BBR inhibits the progression of hepatocellular carcinoma (HCC) by modulating HIF-1α expression.

View Article and Find Full Text PDF

: We assessed the influence of long-term injection of magnoflorine (MAG) on memory acquisition in mice for the first time. : This isoquinoline alkaloid that belongs to the aporphines was isolated from the roots of by centrifugal partition chromatography (CPC) using a biphasic solvent system composed of chloroform: methanol: water in the ratio 4:3:3 (//) with 20 mM of hydrochloric acid and triethylamine, within 64 min. : Our results indicated that long-term injection of MAG 20 mg/kg dose improve the long-term memory acquisition in mice that were evaluated in the passive avoidance (PA) test with no toxicity records.

View Article and Find Full Text PDF

Breast cancer remains a significant challenge in oncology, highlighting the need for alternative therapeutic strategies that target necroptosis to overcome resistance to conventional therapies. Recent investigations into natural compounds have identified 8,12-dimethoxysanguinarine (SG-A) from Eomecon chionantha as a potential necroptosis inducer. This study presents the first computational exploration of SG-A interactions with key necroptotic proteins-RIPK1, RIPK3, and MLKL-through molecular docking, molecular dynamics (MD), density functional theory (DFT), and molecular electrostatic potential (MEP) analyses.

View Article and Find Full Text PDF

Want 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!