Construction of the pyridine ring is a practical and streamline way to construct a variety of quindoline derivatives. We have developed a novel method for synthesis of quindoline derivatives by means of intramolecular ring-closure reactions of 3--methylphenylindoles an iminium salt intermediate. This practical method has the advantages of a short reaction time, operational simplicity, and nearly quantitative yields; and it can be used for the rapid synthesis of a variety of valuable quindoline derivatives.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d3cc05143a | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Design, synthesis, and evaluation of novel quindoline derivatives with fork-shaped side chains as RNA G-quadruplex stabilizers for repressing oncogene NRAS translation.
Eur J Med Chem
May 2024
School of Pharmaceutical Sciences, State Key Laboratory of Oncology in South China, Sun Yat-sen University, Guangzhou, 510006, China. Electronic address:
NRAS mutation is the second most common oncogenic factor in cutaneous melanoma. Inhibiting NRAS translation by stabilizing the G-quadruplex (G4) structure with small molecules seems to be a potential strategy for cancer therapy due to the NRAS protein's lack of a druggable pocket. To enhance the effects of previously reported G4 stabilizers quindoline derivatives, we designed and synthesized a novel series of quindoline derivatives with fork-shaped side chains by introducing (alkylamino)alkoxy side chains.
View Article and Find Full Text PDFMurine Myoblasts Exposed to SYUIQ-5 Acquire Senescence Phenotype and Differentiate into Sarcopenic-Like Myotubes, an In Vitro Study.
J Gerontol A Biol Sci Med Sci
April 2024
Laboratory of Experimental Biochemistry and Molecular Biology, IRCCS Istituto Ortopedico Galeazzi, Milano, Italy.
Article Synopsis
- Aging significantly impacts the musculoskeletal system, with a strong link to the buildup of senescent cells contributing to muscle impairment.
- Researchers developed a new in vitro model using C2C12 mouse myoblasts that exhibit characteristics of sarcopenia when induced to senescence through the telomerase inhibitor SYUIQ-5.
- The resulting senescent myoblasts showed reduced differentiation potential, increased levels of muscle degradation markers, and higher MYOSTATIN release, suggesting that an accumulation of senescent muscle cells may play a role in the development of sarcopenia.
Intramolecular trapping of an iminium salt: rapid construction of quindoline derivatives.
Chem Commun (Camb)
January 2024
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China.
Construction of the pyridine ring is a practical and streamline way to construct a variety of quindoline derivatives. We have developed a novel method for synthesis of quindoline derivatives by means of intramolecular ring-closure reactions of 3--methylphenylindoles an iminium salt intermediate. This practical method has the advantages of a short reaction time, operational simplicity, and nearly quantitative yields; and it can be used for the rapid synthesis of a variety of valuable quindoline derivatives.
View Article and Find Full Text PDFEfficient Buchwald-Hartwig and nitrene-mediated five-membered ring closure approaches to the total synthesis of quindoline. Unexpected direct conversion of a nitro group into a phosphazene.
RSC Adv
May 2023
Instituto de Química Rosario (IQUIR, CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario Suipacha 531 2000 Rosario Argentina
Two total syntheses of quindoline, which take place through the intermediacy of 3-nitroquinoline derivatives, are reported. The general synthetic sequence involves construction of the latter by mechanochemical condensation of benzaldehydes with 2-amino-nitrostyrene, followed either by reduction of the nitro group of the heterocycle and Buchwald-Hartwig cyclization or by a nitrene-mediated cyclization under solventless conditions. Use of PPh to generate the nitrene resulted in the unprecedented formation of a phosphazene in place of quindoline.
View Article and Find Full Text PDFTargeting Parallel Topology of G-Quadruplex Structures by Indole- Fused Quindoline Scaffolds.
Biochemistry
November 2022
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai400076, India.
Preferential stabilization of G-quadruplex (G4) structures using small-molecule ligands has emerged as an effective approach to develop anticancer drugs. Herein, we report the synthesis of three indole-fused quindoline derivatives with varying lengths of side chains (, , ) as selective ligands for promoter G4 structures. The ligands stabilize the parallel topology of and promoter G4 DNAs over telomeric and duplex DNAs, as evident from the circular dichroism melting and polymerase stop-assay experiments.
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!