Journal
ACS COMBINATORIAL SCIENCE
Volume 13, Issue 5, Pages 501-510Publisher
AMER CHEMICAL SOC
DOI: 10.1021/co200090p
Keywords
parallel synthesis; desketoraloxifene; iodocyclization; benzo[b]thiophene; selective estrogen receptor modulator (SERM); palladium coupling
Funding
- National Institute of General Medical Sciences [GM070620, GM079593]
- National Institutes of Health Kansas University Chemical Methodologies and Library Development Center of Excellence [GM069663]
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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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