ArticleEuropean journal of medicinal chemistry2018
Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors.
Article in European journal of medicinal chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 25 citations in OpenAlex.
- Proteins and DNA Sequences Interacting with Tanshinones and Tanshinone Derivatives.International journal of molecular sciences · 2025Review
- In Silico and In Vitro Identification of P-Glycoprotein Inhibitors from a Library of 375 Phytochemicals.International journal of molecular sciences · 2023Article
- Synthesis of illudalic acid and analogous phosphatase inhibitors.Organic & biomolecular chemistry · 2021Article
- One-Pot Synthesis of 4-Carboalkoxy-Substituted Benzo[ACS omega · 2020Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biologically active molecules containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing an array of substituents (methyl, isopropyl, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (K
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