ArticleACS combinatorial science2011
Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling.
Article in ACS combinatorial science, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Choline Chloride/Urea - Promoted Iodocyclization of 3-Alkynylthiophene-2-carboxamides: A Green Synthesis of 4-Iodo-7H-thieno[2,3-c]pyran-7-imines and Their Coupling Reactions in Deep Eutectic Solvents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,Tetrahedron · 2018Article
- BClAngewandte Chemie (International ed. in English) · 2017Article
- Discovery of desketoraloxifene analogues as inhibitors of mammalian, Pseudomonas aeruginosa, and NAPE phospholipase D enzymes.ACS chemical biology · 2015Article
- Solution-phase parallel synthesis of a multisubstituted cyclic imidate library.ACS combinatorial science · 2013Article
- Solution-phase synthesis of a highly substituted furan library.ACS combinatorial science · 2012Article
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4 authors.
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Abstract
For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).
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