25361-54-0Relevant academic research and scientific papers
COMPOUNDS MODULATING PROTEIN RECRUITMENT AND/OR DEGRADATION
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Paragraph 0667; 0668, (2021/06/26)
The invention provides cereblon binders for the degradation of proteins by the ubiquitin proteasome pathway for therapeutic applications.
Improved and scalable synthesis of building blocks for the modular synthesis of teraryl-based alpha-helix mimetics
Trobe, Melanie,Breinbauer, Rolf
, p. 509 - 521 (2016/03/19)
The modular synthesis of teraryl-based alpha-helix mimetics can be accomplished by sequential Suzuki-couplings of arylboronic acid building blocks with 4-iodophenyltriflate core-fragments. We report about new synthetic accesses to core fragments featuring
A modular synthesis of teraryl-based α-helix mimetics, part 1: Synthesis of core fragments with two electronically differentiated leaving groups
Peters, Martin,Trobe, Melanie,Tan, Hao,Kleineweischede, Rolf,Breinbauer, Rolf
supporting information, p. 2442 - 2449 (2013/04/24)
Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics. Central to our strategy is the use of a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd-catalyzed cross-coupling used for terphenyl assembly. With the halogen/diazonium route and the halogen/triflate route, two strategies have successfully been established. The synthesis of core building blocks with aliphatic (Ala, Val, Leu, Ile), aromatic (Phe), polar (Cys, Lys), hydrophilic (Ser, Gln), and acidic (Glu) amino acid side chains are reported. Turn on: Teraryl-based α-helix mimetics can be effectively produced by sequential Suzuki coupling of a central core fragment featuring electronically differentiated leaving groups with aryl boronic pinacol esters (see scheme; dppf=1,1′-bis(diphenylphosphino) ferrocene, DME=dimethoxyethane, Pin=pinacol, Tf=trifluoromethanesulfonyl). With a set of only 2×18 building blocks, all permutations of α-helix mimetics can be produced. Copyright
The AZARYPHOS family of ligands for ambifunctional catalysis: Syntheses and use in ruthenium-catalyzed anti-markovnikov hydration of terminal alkynes
Hintermann, Lukas,Dang, Tuan Thanh,Labonne, Aurelie.,Kribber, Thomas,Xiao, Li,Naumov, Pance
supporting information; experimental part, p. 7167 - 7179 (2010/02/28)
The family of AZARYPHOS (aza-aryl-phosphane) phosphane ligands, containing a phosphine unit and sterically shielded nitrogen lone pairs in the ligand periphery, is introduced as a tool for developing ambifunctional catalysis by the metal center and nitrogen lone pairs in the ligand sphere. General synthetic strategies have been developed to synthesize over 25 examples of structurally diverse (6-aryl-2pyridyl)phosphanes (ARPYPHOS), (6alkyl-2-pyridyl)phosphanes (ALPY-PHOS), 4,6-disubsituted l,3-diazin-2ylphosphanes or l,3,5-triazin-2- ylphosphanes, quinazolinylphosphanes, quinolinylphosphanes, and others. The scalable syntheses proceed in a few steps. The incorporation of AZARYPHOS ligands (L) into complexes [RuCp(L)2(MeCN)][PF6] (Cp = cyclopentadieny1)gives catalysts for the anti-Markovnikov hydration of terminal alkynes of the highest known activities. Electronic and steric ligand effects modulate the reaction kinetics over a range of two orders of magnitude. These results highlight the importance of using structurally diverse ligand families in the process of developing cooperative ambifunctional catalysis by a metal and its ligand.
Syntheses of highly functionalised 6-substituted pteridines.
Guiney, Donie,Gibson, Colin L,Suckling, Colin J
, p. 664 - 675 (2007/10/03)
Methods for the synthesis of polyfunctional 6-substituted pteridines from the corresponding 6-aldehydes are described. Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy and dihydroxy functional groups have all been introduced principally through
