Highly functionalized pyrrolidine analogues: stereoselective synthesis and caspase-dependent apoptotic activity.

RSC Adv

Unidad de Química Orgánica y Farmacéutica, Departamento de Química en Ciencias Farmacéuticas, Facultad de Farmacia, Universidad Complutense 28040 Madrid Spain.

Published: December 2018

Novel spiropyrrolidine heterocyclic hybrids were synthesized for the first time in a sustainable fashion employing a 1,3-dipolar cycloaddition strategy to form a new class of azomethine ylides generated from tyrosine and acenaphthenequinone. Following their synthesis and characterization, these heterocyclic hybrids were tested for their anticancer activities by incubation at different concentrations and durations with different cancer and non-cancer cell cultures, and the results indicated a potential therapeutic activity. Further analysis of cancer cell death revealed that it occurred through a caspase-related apoptotic pathway, specifically mediated by caspase-3. These results demonstrated that the obtained spiropyrrolidine heterocyclic hybrids may be good hit compounds for the development of potential therapeutic agents for the treatment of malignant tumors.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9091711PMC
http://dx.doi.org/10.1039/c8ra07985dDOI Listing

Publication Analysis

Top Keywords

heterocyclic hybrids
12
spiropyrrolidine heterocyclic
8
potential therapeutic
8
highly functionalized
4
functionalized pyrrolidine
4
pyrrolidine analogues
4
analogues stereoselective
4
stereoselective synthesis
4
synthesis caspase-dependent
4
caspase-dependent apoptotic
4

Similar Publications

Experimental and Theoretical Study of Two 3D Difunctional Electrocatalytic Hybrid Vanadate-Containing Metal-Organic Motifs.

Inorg Chem

January 2025

Key Laboratory of Polyoxometalate Science of Ministry of Education, Faculty of Chemistry, Northeast Normal University, Changchun, Jilin 130024, PR China.

Two novel 3D inorganic-organic hybrids based on [VO]/[VO] clusters, [Cu(bbpy)(VO)]·3HO () and [CuAg(pty)(VO)]·HO () (bbpy = 3,5-bis(1-benzimidazole) pyridine, pty = 4'-(4″-pyridyl)-2,2':6',2″-terpyridine), were isolated in the same POV/Cu/N-heterocycle ligand reaction systems. Hybrids and possess novel three-dimensional bimetallic frameworks derived from [VO]/[VO] clusters and Cu-organic complexes. In , bbpy ligands are grafted by Cu to a grid ribbon 2D sheet, which are connected with benzene-like [VO] to yield a 3D framework.

View Article and Find Full Text PDF

A range of heterocyclic compounds, including Isatin (oneH-indole-2, 3-dione) and its by-products, have been shown to represent potential unit blocks in the synthesis of potential medicinal agents. Numerous studies have been carried out on isatin, its synthesis, biological uses, and its chemical composition since when it was discovered. Functionally, these isatin-containing heterocycles have demonstrated antibacterial, antidiabetic, antiviral, antitubercular, and anticancer properties, among many others.

View Article and Find Full Text PDF

Dinitramide salts based on nitropyrazole-diaminotriazole hybrid: novel ionic energetic materials with high-energy and low-sensitivity.

Phys Chem Chem Phys

January 2025

Experimental Center of Advanced Materials, School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.

In this study, employing a simple anion exchange strategy and straightforward three-step synthetic route, a pair of promising nitrogen-rich heterocyclic cation and oxygen-rich anion were assembled together to generate two novel dinitramide energetic salts, both of which exhibit prominent detonation performance comparable to benchmark explosive RDX while possessing significantly lower mechanical sensitivity than RDX, thereby highlighting them as promising candidates for advanced secondary explosives. This work has directly led to a practical protocol for the design of chloride-free environmentally friendly IEMs, and accelerates the development of organic explosives with high-energy and low-sensitivity.

View Article and Find Full Text PDF

Background: In the era of resistance, the design and search for new "small" molecules with a narrow spectrum of activity that target a protein or enzyme specific to a certain bacterium with high selectivity and minimal side effects remains an urgent problem of medicinal chemistry. In this regard, we developed and successfully implemented a strategy for the search for new hybrid molecules, namely, the not broadly known [2-(3-R-1-[1,2,4]-triazol-5-yl)phenyl]amines. They can act as "building blocks" and allow for the introduction of certain structural motifs into the desired final products in order to enhance the antistaphylococcal effect.

View Article and Find Full Text PDF

Photosynthesis, which is the foundation of crop growth and development, is accompanied by complex transcriptional regulatory mechanisms. Research has established that brassinosteroids (BRs) play a role in regulating plant photosynthesis, with the majority of research focusing on the physiological level and regulation of rate-limiting enzymes in the dark reactions of photosynthesis. However, studies on their effects on maize photosynthesis, specifically on light-harvesting antenna proteins, have yet to be conducted.

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!