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Structure-activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene.

Abstract：

:The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon alpha-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (>1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Appendino G,Ech-Chahad A,Minassi A,De Petrocellis L,Di Marzo V

doi

10.1016/j.bmcl.2009.11.035

subject

Has Abstract

pub_date

2010-01-01 00:00:00

pages

97-9

issue

1

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(09)01605-9

journal_volume

20

pub_type

杂志文章

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