118811-34-0Relevant articles and documents
Identification of a selective, activity-based probe for glyceraldehyde 3-phosphate dehydrogenases
Kaschani, Farnusch,Clerc, Jerome,Krahn, Daniel,Bier, David,Hong, Tram Ngoc,Ottmann, Christian,Niessen, Sherry,Colby, Tom,Van Der Hoorn, Renier A. L.,Kaiser, Markus
, p. 5230 - 5233 (2012)
Exceptionally specific: The natural-product-like structural complexity of a bicyclic hydantoin was exploited to generate the novel, highly specific activity-based profiling probe (ABPP) Mrl-Rh (Rh=rhodamine; see picture) for glyceraldehyde 3-phosphate dehydrogenases. This probe can be used to investigate activity changes of this enzyme class during plant-pathogen interactions. Copyright
Amidoalkylindoles as Potent and Selective Cannabinoid Type 2 Receptor Agonists with in Vivo Efficacy in a Mouse Model of Multiple Sclerosis
Shi, Ying,Duan, Yan-Hui,Ji, Yue-Yang,Wang, Zhi-Long,Wu, Yan-Ran,Gunosewoyo, Hendra,Xie, Xiao-Yu,Chen, Jian-Zhong,Yang, Fan,Li, Jing,Tang, Jie,Xie, Xin,Yu, Li-Fang
, p. 7067 - 7083 (2017)
Selective CB2 agonists represent an attractive therapeutic strategy for the treatment of a variety of diseases without psychiatric side effects mediated by the CB1 receptor. We carried out a rational optimization of a black market designer drug SDB-001 that led to the identification of potent and selective CB2 agonists. A 7-methoxy or 7-methylthio substitution at the 3-amidoalkylindoles resulted in potent CB2 antagonists (27 or 28, IC50 = 16-28 nM). Replacement of the amidoalkyls from 3-position to the 2-position of the indole ring dramatically increased the agonist selectivity on the CB2 over CB1 receptor. Particularly, compound 57 displayed a potent agonist activity on the CB2 receptor (EC50 = 114-142 nM) without observable agonist or antagonist activity on the CB1 receptor. Furthermore, 57 significantly alleviated the clinical symptoms and protected the murine central nervous system from immune damage in an experimental autoimmune encephalomyelitis (EAE) mouse model of multiple sclerosis.
Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3
Hoshino, Yoshihiko,Iwabuchi, Yoshiharu,Kuriyama, Yuse,Sasano, Yusuke,Uesugi, Shun-ichiro,Yamaichi, Aoto
, p. 1961 - 1965 (2021/01/04)
Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.
(4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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Paragraph 0878; 0879, (2019/05/15)
The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).