7280-81-1Relevant articles and documents
Discovery of Orally Bioavailable Purine-Based Inhibitors of the Low-Molecular-Weight Protein Tyrosine Phosphatase
Stanford, Stephanie M.,Diaz, Michael A.,Ardecky, Robert J.,Zou, Jiwen,Roosild, Tarmo,Holmes, Zachary J.,Nguyen, Tiffany P.,Hedrick, Michael P.,Rodiles, Socorro,Guan, April,Grotegut, Stefan,Santelli, Eugenio,Chung, Thomas D. Y.,Jackson, Michael R.,Bottini, Nunzio,Pinkerton, Anthony B.
supporting information, p. 5645 - 5653 (2021/05/31)
Obesity-associated insulin resistance plays a central role in the pathogenesis of type 2 diabetes. A promising approach to decrease insulin resistance in obesity is to inhibit the protein tyrosine phosphatases that negatively regulate insulin receptor signaling. The low-molecular-weight protein tyrosine phosphatase (LMPTP) acts as a critical promoter of insulin resistance in obesity by inhibiting phosphorylation of the liver insulin receptor activation motif. Here, we report development of a novel purine-based chemical series of LMPTP inhibitors. These compounds inhibit LMPTP with an uncompetitive mechanism and are highly selective for LMPTP over other protein tyrosine phosphatases. We also report the generation of a highly orally bioavailable purine-based analogue that reverses obesity-induced diabetes in mice.
Synthetic strategies to 9-substituted 8-oxoadenines
Siah, Huey-San Melanie,Gundersen, Lise-Lotte
supporting information, p. 1469 - 1476 (2013/05/09)
Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
EASY ALKYLATION OF PURINE BASES BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT SOLVENT. STRUCTURAL ANALYSIS BY 2D HETERONUCLEAR 1H 13C CORRELATED NMR SPECTROSCOPY
Platzer, Nicole,Galons, Herve,Bensaid, Younes,Miocque, Marcel,Bram, Georges
, p. 2101 - 2108 (2007/10/02)
Solid-liquid PTC without added organic solvent promotes alkylation of purine derivatives leading in particular to an efficient synthesis of the antiviral DHPA.The location of the substituent on the ring was determined by analysis of coupling interactions
