ArticleOrganic & biomolecular chemistry2020
Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity.
Article in Organic & biomolecular chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 22 citations in OpenAlex.
- Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.RSC advances · 2025Review
- Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles.International journal of molecular sciences · 2023Article
- Does electrophilic activation of nitroalkanes in polyphosphoric acid involve formation of nitrile oxides?RSC advances · 2021Article
- Electrophilically Activated Nitroalkanes in Double Annulation of [1,2,4]Triazolo[4,3-Molecules (Basel, Switzerland) · 2021Article
- [3 + 2]-Annulation of pyridinium ylides with 1-chloro-2-nitrostyrenes unveils a tubulin polymerization inhibitor.Organic & biomolecular chemistry · 2021Article
- Electrophilically Activated Nitroalkanes in Synthesis of 3,4-Dihydroquinozalines.Molecules (Basel, Switzerland) · 2021Article
- Synthesis of imidazo[1,5-Beilstein journal of organic chemistry · 2020Article
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Authors and funding
10 authors at 3 institutions in 3 countries.
Funding
Abstract
We discovered a reaction of nitroalkanes with 2-hydrazinylquinolines, 2-hydrazinylpyridines and bis-2,4-dihydrazinylpyrimidines in polyphosphoric acid (PPA) affording 1,2,4-triazolo[4,3-a]quinolines, 1,2,4-triazolo[4,3-a]pyridines and bis[1,2,4]triazolo[4,3-a:4',3'-c]pyrimidines, respectively. The reaction expands the scope of heterocyclic annulations involving phosphorylated nitronates, believed to be the electrophilic intermediates formed from nitroalkanes in PPA. Several of the synthesized triazoles showed promising anticancer activity by inducing differentiation in neuroblastoma cancer cells. Due to the urgent need for novel differentiation agents for neuroblastoma therapy, this finding warrants further evaluation of this class of compounds against neuroblastoma.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.