Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

A [3 + 2] 1,3-Dipolar cycloaddition of ,-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8156229PMC
http://dx.doi.org/10.3390/molecules26102969DOI Listing

Publication Analysis

Top Keywords

tetrahydroisoquinoline derivatives
8
13-dipolar cycloaddition
8
cycloaddition -cyclic
8
-cyclic azomethine
8
azomethine imines
8
imines allyl
8
allyl alkyl
8
alkyl ketones
8
asymmetric synthesis
4
synthesis tetrahydroisoquinoline
4

Similar Publications

Discovery of 2-tetrahydroisoquinoline substituted quinazoline derivatives as lysine methyltransferase G9a inhibitors with in vivo antitumor efficacy.

Eur J Med Chem

September 2025

Shanghai Frontiers Science Center of Drug Target Identification and Delivery, National Key Laboratory of Innovative Immunotherapy, School of Pharmaceutical Sciences, Shanghai Jiao Tong University, Shanghai, 200240, China; State Key Laboratory of Innovative Immunotherapy, Central Research Institute,

Overexpression of protein lysine methyltransferase G9a, which catalyzes mono- and di-methylation of histone H3K9 and non-histone proteins, is closely associated with poor prognosis and metastasis of various cancers. Here, we designed and synthesized a series of novel G9a inhibitors bearing 2-tetrahydroisoquinoline substituted quinazoline scaffold. Among them, compound 31 with 2-dioxole fused tetrahydroisoquinoline exhibited the most potent inhibitory effects against G9a with an IC value of 0.

View Article and Find Full Text PDF

Background: Familial Alzheimer's disease (fAD) is a hereditary disease that develops at an unusually early age. The deposition of toxic amyloid-beta (Aβ) is a hallmark of fAD. Despite their genetic origin and increasing prevalence, no effective drugs currently exist.

View Article and Find Full Text PDF

Rational discovery of novel tetrahydroisoquinoline-indole derivatives as potent P-glycoprotein inhibitor against multidrug resistance in MCF-7/ADR cell.

Bioorg Chem

August 2025

Department of Infectious Diseases & Anhui Province Key Laboratory of Infectious Diseases, The First Affiliated Hospital of Anhui Medical University, Hefei 230022, China; School of Biological Sciences, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China. Electronic address: liyasheng@ahm

A key strategy for overcoming multidrug resistance (MDR) involves developing inhibitors for the chemotherapy drug efflux pump, P-glycoprotein (P-gp). In this study, building on the prior exploration of the tetrahydroisoquinoline-indole scaffold and receptor-based drug design, the amino group on the indole underwent nucleophilic substitution, leading to 20 novel tetrahydroisoquinoline-benzyl-1H-indole derivatives. The exploration of structure-activity relationships (SAR) revealed that compound BP3p exhibited low cytotoxicity and potent MDR reversal activity against doxorubicin in MCF7/ADR cells (IC = 0.

View Article and Find Full Text PDF

CD44-targeted N-benzyltetrahydroisoquinoline derivatives as anticancer agents with high tumor-to-normal cell selectivity.

Eur J Med Chem

November 2025

Department of Medicinal and Organic Chemistry and Excellence Research Unit of Chemistry Applied to Biomedicine and the Environment, Faculty of Pharmacy, University of Granada, Campus Cartuja s/n, 18071, Granada, Spain; Instituto de Investigación Biosanitaria ibs.GRANADA, 18012, Granada, Spain. Elec

CD44, a cell surface glycoprotein, plays a crucial role in cancer progression by enhancing cell proliferation and resistance to apoptosis. Targeting CD44 with small molecules is a promising cancer therapy strategy. Building on our previous work with the tetrahydroisoquinoline (THIQ) derivative SRT1, we designed and synthesized a series of analogues (SRT2-SRT10) to explore their anticancer potential.

View Article and Find Full Text PDF

Higenamine hydrochloride prevents renal inflammation and fibrosis in diabetic nephropathy by inhibiting the STAT3 signaling pathway.

Toxicol Appl Pharmacol

October 2025

Jiangsu Marine Pharmaceutical Resources Development Engineering Research Center, Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, College of Pharmacy, Jiangsu Ocean University, Lianyungang 222005, China. Electronic address:

Higenamine Hydrochloride (HGN) is an alkaloid derived from the traditional Chinese medicinal herb Aconite, possesses pharmacological activities such as anti-inflammatory and antioxidant properties. Its specific role in diabetic nephropathy (DN) remains unknown. The purpose of this work was to investigate the protective impact of HGN against streptozotocin (STZ)-induced renal inflammation and fibrosis in DN mice, as well as to investigate its probable mechanism of action in vitro using high glucose (HG)-treated HK-2 cells.

View Article and Find Full Text PDF