6-Amino-2-fluoropyridine-3-boronic acid pinacol ester
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6-Amino-2-fluoropyridine-3-boronic acid pinacol ester

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Category
Others
Catalog number
BAT-008832
CAS number
944401-67-6
Molecular Formula
C11H16BFN2O2
Molecular Weight
238.07
6-Amino-2-fluoropyridine-3-boronic acid pinacol ester
IUPAC Name
6-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
Synonyms
2-Amino-6-fluoro pyridine-5-boronic acid pinacol ester; 6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
InChI
InChI=1S/C11H16BFN2O2/c1-10(2)11(3,4)17-12(16-10)7-5-6-8(14)15-9(7)13/h5-6H,1-4H3,(H2,14,15)
InChI Key
URUHDSKWFVRYIP-UHFFFAOYSA-N
Canonical SMILES
B1(OC(C(O1)(C)C)(C)C)C2=C(N=C(C=C2)N)F
1. Syntheses of Benzo[ b]furan-6-carbonitrile and 6-Cyanobenzo[ b]furan-2-boronic Acid Pinacol Ester
John D Williams, Xiaoyuan Ding, Son Nguyen, Kimberly K Vines, Norton P Peet Synth Commun. 2013;43(14):10.1080/00397911.2012.684086. doi: 10.1080/00397911.2012.684086.
6-Cyanobenzo[b]furan-2-boronic acid pinacol ester (10) is a potentially useful 2-point scaffold for the construction of specific compounds or compound libraries with benzofuran cores. Using a per-iodination/de-iodination strategy coupled with a Sonogashira alkynylation and Cu-catalyzed heteroannulation, we have developed a procedure that allows the preparation of benzo[b]furan-6-carbonitrile (9) and 6-cyanobenzo[b]furan-2-boronic acid pinacol ester (10) in gram quantities.
2. Targeted Treatment of Ischemic Stroke by Bioactive Nanoparticle-Derived Reactive Oxygen Species Responsive and Inflammation-Resolving Nanotherapies
Jichao Yuan, et al. ACS Nano. 2021 Oct 26;15(10):16076-16094. doi: 10.1021/acsnano.1c04753. Epub 2021 Oct 4.
Stroke is a primary cause of death and disability worldwide, while effective and safe drugs remain to be developed for its clinical treatment. Herein, we report bioactive nanoparticle-derived multifunctional nanotherapies for ischemic stroke, which are engineered from a pharmacologically active oligosaccharide material (termed as TPCD) prepared by covalently conjugating a radical-scavenging compound (Tempol) and a hydrogen-peroxide-eliminating moiety of phenylboronic acid pinacol ester (PBAP) on β-cyclodextrin. Of note, combined functional moieties of Tempol and PBAP on β-cyclodextrin contribute to antioxidative and anti-inflammatory activities of TPCD. Cellularly, TPCD nanoparticles (i.e., TPCD NPs) reduced oxygen-glucose deprivation-induced overproduction of oxidative mediators, increased antioxidant enzyme expression, and suppressed microglial-mediated inflammation, thereby inhibiting neuronal apoptosis. After intravenous (i.v.) delivery, TPCD NPs could efficiently accumulate at the cerebral ischemic injury site of mice with middle cerebral artery occlusion (MCAO), showing considerable distribution in cells relevant to the pathogenesis of stroke. Therapeutically, TPCD NPs significantly decreased infarct volume and accelerated recovery of neurological function in MCAO mice. Mechanistically, efficacy of TPCD NPs is achieved by its antioxidative, anti-inflammatory, and antiapoptotic effects. Furthermore, TPCD NPs can function as a reactive oxygen species labile nanovehicle to efficiently load and triggerably release an inflammation-resolving peptide Ac2-26, giving rise to an inflammation-resolving nanotherapy (i.e., ATPCD NP). Compared to TPCD NP, ATPCD NP demonstrated notably enhanced in vivo efficacies, largely resulting from its additional inflammation-resolving activity. Consequently, TPCD NP-derived nanomedicines can be further developed as promising targeted therapies for stroke and other inflammation-associated cerebrovascular diseases.
3. Genistein-Derived ROS-Responsive Nanoparticles Relieve Colitis by Regulating Mucosal Homeostasis
Wentao Fan, Shuo Zhang, Yuting Wu, Tao Lu, Jiwen Liu, Xiuyun Cao, Shuhui Liu, Liping Yan, Xizhi Shi, Guangliang Liu, Chaobo Huang, Suquan Song ACS Appl Mater Interfaces. 2021 Sep 1;13(34):40249-40266. doi: 10.1021/acsami.1c09215. Epub 2021 Aug 23.
Disruption of intestinal homeostasis is an important event in the development of inflammatory bowel disease (IBD), and genistein (GEN) is a candidate medicine to prevent IBD. However, the clinical application of GEN is restricted owing to its low oral bioavailability. Herein, a reactive oxygen species (ROS)-responsive nanomaterial (defined as GEN-NP2) containing superoxidase dismutase-mimetic temporally conjugated β-cyclodextrin and 4-(hydroxymethyl)phenylboronic acid pinacol ester-modified GEN was prepared. GEN-NP2 effectively delivered GEN to the inflammation site and protected GEN from rapid metabolism and elimination in the gastrointestinal tract. In response to high ROS levels, GEN was site-specifically released and accumulated at inflammatory sites. Mechanistically, GEN-NP2 effectively increased the expression of estrogen receptor β (ERβ), simultaneously reduced the expression of proinflammatory mediators (apoptosis-associated speck-like protein containing a CARD (ASC) and Caspase1-p20), attenuated the infiltration of inflammatory cells, promoted autophagy of intestinal epithelial cells, inhibited the secretion of interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α), modulated the gut microbiota, and ultimately alleviated colitis. In addition, the oral administration of these nanoparticles showed excellent safety, thereby providing confidence in the further development of precise treatments for IBD.
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