309922-87-0

Basic information

• Product Name: 3-Amino-5-bromobenzofuran-2-carboxamide
• Synonyms: 3-Amino-5-bromobenzofuran-2-carboxamide
• CAS NO: 309922-87-0
• Molecular Formula: C₉H₇BrN₂O₂
• Molecular Weight: 255.06808
• Mol File: 309922-87-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Amino-5-bromobenzofuran-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-5-bromobenzofuran-2-carboxamide(309922-87-0)
• EPA Substance Registry System: 3-Amino-5-bromobenzofuran-2-carboxamide(309922-87-0)

Safety Data

• Hazardous Substances Data: 309922-87-0(Hazardous Substances Data)

Upstream product

• 40530-18-5 5-bromo-2-hydroxybenzonitrile 
• 318259-87-9 2-(4-bromo-2-cyanophenoxy)acetamide 

Downstream Products

• 1169560-14-8 C₁₆H₁₀BrClN₂O₂ 
• 1169550-05-3 8-bromo-2-(2-hydroxyphenyl)[1]benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 1169551-55-6 8-bromo-2-[2-chloro-4-(methylsulfonyl)phenyl][1]benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 1169549-69-2 8-bromo-2-(2-chloro-4-nitrophenyl)[1]benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 1169559-16-3 5-bromo-3-(2-chloroacetamido)benzofuran-2-carboxamide 
• 1380495-98-6 3-amino-5-phenylbenzofuran-2-carboxamide 
• 1169549-63-6 8-bromo-2-(2-chlorophenyl)[1]benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 1169549-73-8 8-bromo-2-{2-chloro-4-[(piperidin-4-ylmethyl)amino]phenyl}[1]benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 1169552-62-8 N-[4-(8-bromo-4-oxo-3,4-dihydro[1]benzofuro[3,2-d]pyrimidin-2-yl)-3-chlorophenyl]-3-piperidin-1-ylpropanamide 
• 1169556-15-3 C₂₄H₂₂BrClN₄O₃ 
• 1380496-05-8 C₁₇H₈BrClN₂O₄ 
• 1169549-71-6 2-(4-amino-2-chlorophenyl)-8-bromo[1]benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 1350197-58-8 C₁₈H₁₀BrClN₂O₄ 

Relevant articles and documents

Preclinical development of fa5, a novel amp-activated protein kinase (Ampk) activator as an innovative drug for the management of bowel inflammation

Acadesine (ACA), a pharmacological activator of AMP-activated protein kinase (AMPK), showed a promising beneficial effect in a mouse model of colitis, indicating this drug as an alternative tool to manage IBDs. However, ACA displays some pharmacodynamic limitations precluding its therapeutical applications. Our study was aimed at evaluating the in vitro and in vivo effects of FA-5 (a novel direct AMPK activator synthesized in our laboratories) in an experimental model of colitis in rats. A set of experiments evaluated the ability of FA5 to activate AMPK and to compare the efficacy of FA5 with ACA in an experimental model of colitis. The effects of FA-5, ACA, or dexamethasone were tested in rats with 2,4-dinitrobenzenesulfonic acid (DNBS)-induced colitis to assess systemic and tissue inflammatory parameters. In in vitro experiments, FA5 induced phospho-rylation, and thus the activation, of AMPK, contextually to the activation of SIRT-1. In vivo, FA5 counteracted the increase in spleen weight, improved the colon length, ameliorated macroscopic damage score, and reduced TNF and MDA tissue levels in DNBS-treated rats. Of note, FA-5 displayed an increased anti-inflammatory efficacy as compared with ACA. The novel AMPK activator FA-5 displays an improved anti-inflammatory efficacy representing a promising pharmacological tool against bowel inflammation.

BENZOFURAN DERIVATIVES FOR USE AS AMPK ACTIVATORS

The present invention refers to benzofuran derivatives, capable of efficaciously activating the enzymatic complex AMPK, useful for the prophylaxis and therapeutic treatment of diseases and disorders in particular metabolic disorders such as diabetes and obesity, immune-mediated inflammatory pathologies and tumours.

Discovery of XL413, a potent and selective CDC7 inhibitor

CDC7 is a serine/threonine kinase that has been shown to be required for the initiation and maintenance of DNA replication. Up-regulation of CDC7 is detected in multiple tumor cell lines, with inhibition of CDC7 resulting in cell cycle arrest. In this paper, we disclose the discovery of a potent and selective CDC7 inhibitor, XL413 (14), which was advanced into Phase 1 clinical trials. Starting from advanced lead 3, described in a preceding communication, we optimized the CDC7 potency and selectivity to demonstrate in vitro CDC7 dependent cell cycle arrest and in vivo tumor growth inhibition in a Colo-205 xenograft model.

The design, synthesis, and biological evaluation of PIM kinase inhibitors

A series of substituted benzofuropyrimidinones with pan-PIM activities and excellent selectivity against a panel of diverse kinases is described. Initial exploration identified aryl benzofuropyrimidinones that were potent, but had cell permeability limitation. Using X-ray crystal structures of the bound PIM-1 complexes with 3, 5m, and 6d, we were able to guide the SAR and identify the alkyl benzofuropyrimidinone (6l) with good PIM potencies, permeability, and oral exposure.

BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS

A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.