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Discovery of 2,6-difluorobenzyl ether series of phenyl ((R)-3-phenylpyrrolidin-3-yl)sulfones as surprisingly potent, selective and orally bioavailable RORγt inverse agonists.

Abstract：

:In an effort to discover oral inverse agonists of RORγt to treat inflammatory diseases, a new 2,6-difluorobenzyl ether series of cyclopentyl sulfones were found to be surprisingly more potent than the corresponding alcohol derivatives. When combined with a more optimized phenyl ((R)-3-phenylpyrrolidin-3-yl)sulfone template, the 2,6-difluorobenzyl ethers yielded a set of very potent RORγt inverse agonists (e.g., compound 26, RORγt Gal4 EC50 11 nM) that are highly selective against PXR, LXRα and LXRβ. After optimizing for stability in human and mouse liver microsomes, compounds 29 and 38 were evaluated in vivo and found to have good oral bioavailability (56% and 101%, respectively) in mice. X-ray co-crystal structure of compound 27 in RORγt revealed that the bulky benzyl ether group causes helix 11 of the protein to partially uncoil to create a new, enlarged binding site, which nicely accommodates the benzyl ether moiety, leading to net potency gain.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Duan JJ,Jiang B,Lu Z,Stachura S,Weigelt CA,Sack JS,Khan J,Ruzanov M,Wu DR,Yarde M,Shen DR,Zhao Q,Salter-Cid LM,Carter PH,Murali Dhar TG

doi

10.1016/j.bmcl.2020.127441

subject

Has Abstract

pub_date

2020-10-01 00:00:00

pages

127441

issue

19

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(20)30552-7

journal_volume

30

pub_type

杂志文章

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