- Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
-
Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.
- Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori
-
p. 8738 - 8741
(2021/09/08)
-
- Anti-Markovnikov hydroazidation of activated olefins via organic photoredox catalysis
-
Organic azides serve as synthetically useful surrogates for primary amines, a functional group which is ubiquitous in bioactive and medicinally relevant molecules. Historically, the formal hydroazidation of simple activated olefins and styrenes has proven
- Nicewicz, David A.,Onuska, Nicholas P. R.,Rosario Collazo, José L.,Schutzbach-Horton, Megan E.
-
supporting information
p. 55 - 59
(2019/12/30)
-
- Small Molecule Microarray Based Discovery of PARP14 Inhibitors
-
Poly(ADP-ribose) polymerases (PARPs) are key enzymes in a variety of cellular processes. Most small-molecule PARP inhibitors developed to date have been against PARP1, and suffer from poor selectivity. PARP14 has recently emerged as a potential therapeutic target, but its inhibitor development has trailed behind. Herein, we describe a small molecule microarray-based strategy for high-throughput synthesis, screening of >1000 potential bidentate inhibitors of PARPs, and the successful discovery of a potent PARP14 inhibitor H10 with >20-fold selectivity over PARP1. Co-crystallization of the PARP14/H10 complex indicated H10 bound to both the nicotinamide and the adenine subsites. Further structure–activity relationship studies identified important binding elements in the adenine subsite. In tumor cells, H10 was able to chemically knockdown endogenous PARP14 activities.
- Peng, Bo,Thorsell, Ann-Gerd,Karlberg, Tobias,Schüler, Herwig,Yao, Shao Q.
-
supporting information
p. 248 - 253
(2016/12/30)
-
- Fused Bicyclic Caspase-1 Inhibitors Assembled by Copper-Free Strain-Promoted Alkyne–Azide Cycloaddition (SPAAC)
-
Challenges exist in the development of potent and selective small-molecule inhibitors against caspase-1. Herein, by making use of the copper-free strain-promoted alkyne–azide cycloaddition (SPAAC) reaction between difluorinated cyclooctynes (DIFOs) and va
- Qian, Linghui,Zhang, Chong-Jing,Wu, Ji'en,Yao, Shao Q.
-
supporting information
p. 360 - 369
(2017/01/17)
-
- Stereochemistry of Aliphatic Carbocations, 15. Rearrangements in 2-Arylalkyl Systems
-
Phenyl shifts from secondary to primary carbon proceed with virtually complete inversion at the migration origin, regardless whether they are induced by solvolysis of the aryl sulfonate 25 or by deamination of the amines 12, 17, 26, and 43.Sequential rearrangements (Ph, CH3 and Ph, H) are likewise stereo- and regiospecific.These results strongly support the intervention of phenonium ions.In contrast, the competitive alkyl shifts (deamination only) from benzylic to primary carbon produce but a small excess of inversion (Me 27percent, Et 13percent, iPr 20percent, tBu 3percent).Obviously, benzyl cations are the predominant intermediates.
- Kirmse, Wolfgang,Guenther, Bernd-Rainer,Loosen, Karin
-
p. 2140 - 2153
(2007/10/02)
-