ArticleProceedings of the National Academy of Sciences of the United States of America2011
Fragment-based domain shuffling approach for the synthesis of pyran-based macrocycles.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 39 citations in OpenAlex.
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- MacroEvoLution: A New Method for the Rapid Generation of Novel Scaffold-Diverse Macrocyclic Libraries.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Modular Synthesis of Diverse Natural Product-Like Macrocycles: Discovery of Hits with Antimycobacterial Activity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Structural and conformational determinants of macrocycle cell permeability.Nature chemical biology · 2016Article
- A Multidimensional Diversity-Oriented Synthesis Strategy for Structurally Diverse and Complex Macrocycles.Angewandte Chemie (International ed. in English) · 2016Article
- High-throughput identification of genotype-specific cancer vulnerabilities in mixtures of barcoded tumor cell lines.Nature biotechnology · 2016Article
- Impact of stereospecific intramolecular hydrogen bonding on cell permeability and physicochemical properties.Journal of medicinal chemistry · 2014Article
- A strategy for the diversity-oriented synthesis of macrocyclic scaffolds using multidimensional coupling.Nature chemistry · 2013Article
- Synthesis and profiling of a diverse collection of azetidine-based scaffolds for the development of CNS-focused lead-like libraries.The Journal of organic chemistry · 2012Article
- Build/couple/pair strategy for the synthesis of stereochemically diverse macrolactams via head-to-tail cyclization.ACS combinatorial science · 2012Article
- Synthesis of a novel suppressor of beta-cell apoptosis via diversity-oriented synthesis.ACS medicinal chemistry letters · 2011Article
- Practical asymmetric synthesis of β-hydroxy γ-amino acids via complimentary aldol reactions.Tetrahedron · 2011Article
- Quantifying structure and performance diversity for sets of small molecules comprising small-molecule screening collections.Proceedings of the National Academy of Sciences of the United States of America · 2011Article
- Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold.The Journal of organic chemistry · 2011Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Complexity and the presence of stereogenic centers have been correlated with success as compounds transition from discovery through the clinic. Here we describe the synthesis of a library of pyran-containing macrocycles with a high degree of structural complexity and up to five stereogenic centers. A key feature of the design strategy was to use a modular synthetic route with three fragments that can be readily interchanged or "shuffled" to produce subtly different variants with distinct molecular shapes. A total of 352 macrocycles were synthesized ranging in size from 14- to 16-membered rings. In order to facilitate the generation of stereostructure-activity relationships, the complete matrix of stereoisomers was prepared for each macrocycle. Solid-phase assisted parallel solution-phase techniques were employed to allow for rapid analogue generation. An intramolecular nitrile-activated nucleophilic aromatic substitution reaction was used for the key macrocyclization step.
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