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  • Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.

Efficient synthesis of (+/-)-parasitenone, a novel inhibitor of NF-kappaB.

Bioorganic & medicinal chemistry letters (2009-08-12)
Tsuyoshi Saitoh, Eriko Suzuki, Arisa Takasugi, Rika Obata, Yuichi Ishikawa, Kazuo Umezawa, Shigeru Nishiyama
ABSTRACT

Dehydroxymethylepoxyquinomicin (DHMEQ, 1) is a novel nuclear factor-kappaB (NF-kappaB) inhibitor that inhibits DNA binding of NF-kappaB components including p65. To inspect its biological activity of 1, we synthesized parasitenone (3), possessing the common epoxycyclohexenone moiety of 1. Assessment of the inhibitory activity against NF-kappaB indicated that the epoxycyclohexenone moiety is the most essential element for the NF-kappaB inhibitory activity and the salicylic acid moiety may contribute the binding efficiency and specificity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Salicylic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
Salicylic acid, puriss. p.a., ≥99.0% (T)
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Salicylic acid, ≥99%, FG
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Salicylic acid, meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (calc. to the dried substance)
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Salicylic acid, ACS reagent, ≥99.0%
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Salicylic acid, BioXtra, ≥99.0%
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Salicylic acid, suitable for plant cell culture
Supelco
Salicylic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland