327618-17-7Relevant academic research and scientific papers
Bioisosteric replacement of anilide with benzoxazole: Potent and orally bioavailable antagonists of VLA-4
Lin, Linus S.,Lanza Jr., Thomas J.,Castonguay, Laurie A.,Kamenecka, Theodore,McCauley, Ermenegilda,Van Riper, Gail,Egger, Linda A.,Mumford, Richard A.,Tong, Xinchun,MacCoss, Malcolm,Schmidt, John A.,Hagmann, William K.
, p. 2331 - 2334 (2004)
We have designed and synthesized a series of heterocyclic bioisosteres for an anilide based on molecular modeling. Excellent potency was retained in the benzoxazole and the benzimidazole derivatives, where a hydrogen bond acceptor is appropriately positioned to mimic the amide bond oxygen. The deletion of the hydrogen bond donor (N-H) led to improved lipophilicity and bioavailability. In the process, 9a was identified as a potent, specific, and bioavailable VLA-4 antagonist, while 9c was found to be a potent and bioavailable dual antagonist of VLA-4 and α4β7.
Benzoxazoles as transthyretin amyloid fibril inhibitors: Synthesis, evaluation, and mechanism of action
Razavi, Hossein,Palaninathan, Satheesh K.,Powers, Evan T.,Wiseman, R. Luke,Purkey, Hans E.,Mohamedmohaideen, Nilofar N.,Deechongkit, Songpon,Chiang, Kyle P.,Dendle, Maria T. A.,Sacchettini, James C.,Kelly, Jeffery W.
, p. 2758 - 2761 (2007/10/03)
Benzoxazoles pevent misfolding: Benzoxazole-based inhibitors of transthyretin (TTR) amyloid fibril formation are among the most effective found to date. They stabilize TTR against both acid-mediated misfolding and urea denaturation by raising the activati
