ArticleJournal of medicinal chemistry2012
Structure-activity relationships in human Toll-like receptor 8-active 2,3-diamino-furo[2,3-c]pyridines.
Article in Journal of medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
What it found
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
24 citing papers in PubMed.
- Article
- Design and Synthesis of Polyphenolic Imidazo[4,5-ACS pharmacology & translational science · 2024Article
- Synthesis of Triazolo[4',5':4,5]furo[2,3-ACS omega · 2024Article
- Imidazo[1,2-ACS omega · 2023Article
- Discovery of Novel EGFR Inhibitor Targeting Wild-Type and Mutant Forms of EGFR: In Silico and In Vitro Study.Molecules (Basel, Switzerland) · 2023Article
- Synthesis and immunopharmacological evaluation of novel TLR7 agonistic triazole tethered imidazoquinolines.RSC advances · 2023Article
- Interrupted reactions in chemical synthesis.Nature reviews. Chemistry · 2021Review
- Role of toll-like receptor 7/8 pathways in regulation of interferon response and inflammatory mediators during SARS-CoV2 infection and potential therapeutic options.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2021Review
- Structural evolution of toll-like receptor 7/8 agonists from imidazoquinolines to imidazoles.RSC medicinal chemistry · 2021Review
- Article
- Synthesis of Biologically Active Molecules through Multicomponent Reactions.Molecules (Basel, Switzerland) · 2020Review
- The Groebke-Blackburn-Bienaymé Reaction.European journal of chemistry (Print) · 2019Article
- The emerging chemical patterns applied in predicting human toll-like receptor 8 agonists.MedChemComm · 2018Article
- Transcriptomal signatures of vaccine adjuvants and accessory immunostimulation of sentinel cells by toll-like receptor 2/6 agonists.Human vaccines & immunotherapeutics · 2018Article
- Small-molecule inhibition of TLR8 through stabilization of its resting state.Nature chemical biology · 2018Article
- Indium triflate promoted one-pot multicomponent synthesis of structurally diverse 3-amino-imidazo[1,2-a]pyridines.Molecular diversity · 2017Article
- Virtual Screening Approaches towards the Discovery of Toll-Like Receptor Modulators.International journal of molecular sciences · 2016Review
- Groebke-Blackburn-Bienaymé multicomponent reaction: emerging chemistry for drug discovery.Molecular diversity · 2016Review
- Identification of Adjuvantic Activity of Amphotericin B in a Novel, Multiplexed, Poly-TLR/NLR High-Throughput Screen.PloS one · 2016Article
- Structure-Based Design of Human TLR8-Specific Agonists with Augmented Potency and Adjuvanticity.Journal of medicinal chemistry · 2015Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
In our ongoing search toward identifying novel and synthetically simpler candidate vaccine adjuvants, we hypothesized that the imidazo[1,2-a]pyrazines, readily accessible via the Groebke-Blackburn-Bienaymé multicomponent reaction, would possess sufficient structural similarity with TLR7/8-agonistic imidazoquinolines. With pyridoxal as the aldehyde component, furo[2,3-c]pyridines, rather than the expected imidazo[1,2-a]pyridines, were obtained, which were characterized by NMR spectroscopy and crystallography. Several analogues were found to activate TLR8-dependent NF-κB signaling. In a focused library of furo[2,3-c]pyridines, a distinct SAR was observed with varying substituents at C2. In human PBMCs, none of the furo[2,3-c]pyridines showed any proinflammatory cytokine induction but upregulated several chemokine ligand genes. In immunization studies in rabbits, the most active compound showed prominent adjuvantic effects. The complete lack of proinflammatory cytokine induction coupled with strong adjuvantic activity of the novel furo[2,3-c]pyridines render this hitherto unknown chemotype an attractive class of compounds which are expected to be devoid of local or systemic reactogenicity.
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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.