Binder, Randall J. published the artcileFacile synthesis of 1,2-dione-containing abietane analogs for the generation of human carboxylesterase inhibitors, Application of (3-Methoxy-5-methylphenyl)boronic acid, the publication is European Journal of Medicinal Chemistry (2018), 79-89, database is CAplus and MEDLINE.
Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biol. active mols. 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 analogs containing an array of substituents (Me, iso-Pr, 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 (Ki < 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogs that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biol.
European Journal of Medicinal Chemistry published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Application of (3-Methoxy-5-methylphenyl)boronic acid.
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Ether | (C2H5)2O – PubChem