ArticleJournal of medicinal chemistry2012
A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct.
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 20 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
20 citing papers in PubMed.
- Insights into Free Drug Release from EfficaciousACS chemical biology · 2025Article
- BorylationOrganic & biomolecular chemistry · 2024Article
- Rapid Construction of a Chloromethyl-Substituted Duocarmycin-like Prodrug.Molecules (Basel, Switzerland) · 2023Article
- Applications of palladium-catalyzed C-N cross-coupling reactions in pharmaceutical compounds.RSC advances · 2023Review
- Single Mutation on Trastuzumab Modulates the Stability of Antibody-Drug Conjugates Built Using Acetal-Based Linkers and Thiol-Maleimide Chemistry.Journal of the American Chemical Society · 2022Article
- Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.The Journal of organic chemistry · 2019Review
- Palladium-Catalyzed Decarboxylative ortho-Acylation of Anilines with Carbamate as a Removable Directing Group.ACS omega · 2018Article
- An overview of recent advances in duplex DNA recognition by small molecules.Beilstein journal of organic chemistry · 2018Review
- The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.The Journal of organic chemistry · 2017Article
- 2-Arylaminobenzothiazole-arylpropenone conjugates as tubulin polymerization inhibitors.MedChemComm · 2017Article
- Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.Chemical reviews · 2016Review
- A five-membered lactone prodrug of CBI-based analogs of the duocarmycins.Tetrahedron letters · 2015Article
- Copper-catalyzed intermolecular C(spChemical science · 2015Article
- Asymmetric synthesis of a CBI-based cyclic N-acyl O-amino phenol duocarmycin prodrug.The Journal of organic chemistry · 2014Article
- Antimalarial chemotherapy: artemisinin-derived dimer carbonates and thiocarbonates.Bioorganic & medicinal chemistry letters · 2014Article
- The survival times of malaria-infected mice are prolonged more by several new two-carbon-linked artemisinin-derived dimer carbamates than by the trioxane antimalarial drug artemether.Bioorganic & medicinal chemistry letters · 2014Article
- A fundamental relationship between hydrophobic properties and biological activity for the duocarmycin class of DNA-alkylating antitumor drugs: hydrophobic-binding-driven bonding.Journal of medicinal chemistry · 2013Article
- Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs.Journal of medicinal chemistry · 2013Article
- Article
- Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones.Beilstein journal of organic chemistry · 2013Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
A unique heterocyclic carbamate prodrug of seco-CBI-indole(2) that releases no residual byproduct is reported as a new member of a class of hydrolyzable prodrugs of the duocarmycin and CC-1065 family of natural products. The prodrug was designed to be activated by hydrolysis of a carbamate releasing the free drug without the cleavage release of a traceable extraneous group. Unlike prior carbamate prodrugs examined that are rapidly cleaved in vivo, the cyclic carbamate was found to be exceptionally stable to hydrolysis under both chemical and biological conditions providing a slow, sustained release of the exceptionally potent free drug. An in vivo evaluation of the prodrug found that its efficacy exceeded that of the parent drug, that its therapeutic window of efficacy versus toxicity is much larger than the parent drug, and that its slow free drug release permitted the safe and efficacious use of doses 150-fold higher than the parent compound.
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What OpenQuestion holds
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.