150256-42-1Relevant articles and documents
Solid-Phase Total Synthesis of Dehydrotryptophan-Bearing Cyclic Peptides Tunicyclin B, Sclerotide A, CDA3a, and CDA4a using a Protected β-Hydroxytryptophan Building Block
Diamandas, Matthew,Moreira, Ryan,Taylor, Scott D.
supporting information, p. 3048 - 3052 (2021/05/05)
A new approach to the synthesis of Z-dehydrotryptophan (ΔTrp) peptides is described. This approach uses Fmoc-β-HOTrp(Boc)(TBS)-OH as a building block, which is readily prepared in high yield and incorporated into peptides using solid-phase Fmoc chemistry. The tert-butyldimethylsilyl-protected indolic alcohol is eliminated during global deprotection/resin cleavage to give ΔTrp peptides exclusively as the thermodynamically favored Z isomer. This approach was applied to the solid-phase synthesis of tunicyclin B, sclerotide A, CDA3a, and CDA4a.
Discovery of Novel Nonpeptidic PAR2 Ligands
Gmeiner, Peter,Hübner, Harald,Kaindl, Jonas,Kl?sel, Ilona,Schmidt, Maximilian F.,Weikert, Dorothee
supporting information, p. 1316 - 1323 (2020/07/04)
Proteinase-activated receptor 2 (PAR2) is a class A G protein-coupled receptor whose activation has been associated with inflammatory diseases and cancer, thus representing a valuable therapeutic target. Pathophysiological roles of PAR2 are often characterized using peptidic PAR2 agonists. Peptidic ligands are frequently unstable in vivo and show poor bioavailability, and only a few approaches toward drug-like nonpeptidic PAR2 ligands have been described. The herein-described ligand 5a (IK187) is a nonpeptidic PAR2 agonist with submicromolar potency in a functional assay reflecting G protein activation. The ligand also showed substantial β-arrestin recruitment. The development of the compound was guided by the crystal structure of PAR2, when the C-terminal end of peptidic agonists was replaced by a small molecule based on a disubstituted phenylene scaffold. IK187 shows preferable metabolic stability and may serve as a lead compound for the development of nonpeptidic drugs addressing PAR2.
Quinazolinones
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Page/Page column 14, (2008/06/13)
Quinazolinones of formula (I) in which R, R1, R2, R3, R4, Y, n and m have the meaning indicated in Patent claim 1, and their salts or solvates as glycoprotein IbIX antagonists
