866775-09-9

Basic information

• Product Name: 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER;methyl 3-amino-6-bromopyridine-2-carboxylate;Methyl 3-aMino-6-broMopicolinate;2-Pyridinecarboxylic acid, 3-aMino-6-broMo-, Methyl ester
• CAS NO: 866775-09-9
• Molecular Formula: C₇H₇BrN₂O₂
• Molecular Weight: 231.048
• Mol File: 866775-09-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 353.439°C at 760 mmHg
• Flash Point: 167.554°C
• Appearance: /
• Density: 1.662g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -0.07±0.10(Predicted)
• CAS DataBase Reference: 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER(866775-09-9)
• EPA Substance Registry System: 3-AMINO-6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER(866775-09-9)

Safety Data

• Hazardous Substances Data: 866775-09-9(Hazardous Substances Data)

Usage

Uses

Methyl 3-amino-6-bromopicolinate is a useful reactant for organic reactions and synthesis.

InChI:InChI=1/C7H7BrN2O2/c1-12-7(11)6-4(9)2-3-5(8)10-6/h2-3H,9H2,1H3

Upstream product

• 1462-86-8 3-amino-pyridine-2-carboxylic acid 
• 36052-27-4 methyl 3-aminopicolinate 

Downstream Products

• 1380571-68-5 (3-amino-6-bromopyridin-2-yl)methanol 
• 1052707-98-8 3-amino-6-(2,6-difluoro-phenyl)-pyridine-2-carboxylic acid [4-(6-amino-2-trifluoromethyl-pyrimidin-4-yl)-pyridin-3-yl]-amide 
• 1052708-06-1 3-amino-6-(2,6-difluoro-phenyl)-pyridine-2-carboxylic acid [4-(6-amino-2-methyl-pyrimidin-4-yl)-pyridin-3-yl]-amide 

Relevant articles and documents

Structure-Based Design of Highly Potent Toll-like Receptor 7/8 Dual Agonists for Cancer Immunotherapy

Activation of the toll-like receptors 7 and 8 has emerged as a promising strategy for cancer immunotherapy. Herein, we report the design and synthesis of a series of pyrido[3,2-d]pyrimidine-based toll-like receptor 7/8 dual agonists that exhibited potent and near-equivalent agonistic activities toward TLR7 and TLR8. In vitro, compounds 24e and 25a significantly induced the secretion of IFN-α, IFN-γ, TNF-α, IL-1β, IL-12p40, and IP-10 in human peripheral blood mononuclear cell assays. In vivo, compounds 24e, 24m, and 25a significantly suppressed tumor growth in CT26 tumor-bearing mice by remodeling the tumor microenvironment. Additionally, compounds 24e, 24m, and 25a markedly improved the antitumor activity of PD-1/PD-L1 blockade. In particular, compound 24e combined with the anti-PD-L1 antibody led to complete tumor regression. These results demonstrated that TLR7/8 agonists (24e, 24m, and 25a) held great potential as single agents or in combination with PD-1/PD-L1 blockade for cancer immunotherapy.

Dual-Stage Picolinic Acid-Derived Inhibitors of Toxoplasma gondii

Toxoplasma gondii causes a prevalent human infection for which only the acute stage has an FDA-approved therapy. To find inhibitors of both the acute stage parasites and the persistent cyst stage that causes a chronic infection, we repurposed a compound library containing known inhibitors of parasitic hexokinase, the first step in the glycolysis pathway, along with a larger collection of new structural derivatives. The focused screen of 22 compounds showed a 77% hit rate (>50% multistage inhibition) and revealed a series of aminobenzamide-linked picolinic acids with submicromolar potency against both T. gondii parasite forms. Picolinic acid 23, designed from an antiparasitic benzamidobenzoic acid class with challenging ADME properties, showed 60-fold-enhanced solubility, a moderate LogD7.4, and a 30% improvement in microsomal stability. Furthermore, isotopically labeled glucose tracing revealed that picolinic acid 23 does not function by hexokinase inhibition. Thus, we report a new probe scaffold to interrogate dual-stage inhibition of T. gondii.

FUSED QUADRACYCLIC COMPOUNDS, COMPOSITIONS AND USES THEREOF

Provided herein are substituted fused quadracyclic compounds useful as inhibitors of MK2. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention also provides medical uses of substituted fused quadracyclic compounds.