62878-96-0

Basic information

• Product Name: 5-BROMOBENZO[B]FURAN-2-CARBONYL CHLORIDE
• Synonyms: 5-BROMOBENZO[B]FURAN-2-CARBONYL CHLORIDE;5-BROMO-1-BENZOFURAN-2-CARBONYL CHLORIDE;5-Bromobenzo[b]furane-2-carbonylchloride
• CAS NO: 62878-96-0
• Molecular Formula: C9H4BrClO2
• Molecular Weight: 259.48
• Mol File: 62878-96-0.mol

Chemical Properties

• Melting Point: 106 °C
• Boiling Point: 319.2°C at 760 mmHg
• Flash Point: 146.8°C
• Appearance: /
• Density: 1.742g/cm³
• Vapor Pressure: 0.000345mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 5-BROMOBENZO[B]FURAN-2-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOBENZO[B]FURAN-2-CARBONYL CHLORIDE(62878-96-0)
• EPA Substance Registry System: 5-BROMOBENZO[B]FURAN-2-CARBONYL CHLORIDE(62878-96-0)

Safety Data

• Hazardous Substances Data: 62878-96-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H4BrClO2/c10-6-1-2-7-5(3-6)4-8(13-7)9(11)12/h1-4H

Upstream product

• 10242-11-2 5-bromobenzo[b]furan-2-carboxylic acid 
• 84102-69-2 5-bromo-benzofuran-2-carboxylic acid ethyl ester 
• 1761-61-1 5-bromosalicyclaldehyde 
• 26028-36-4 5-bromo-2-benzofurancarboxylic acid methyl ester 

Downstream Products

• 62878-86-8 5-bromo-benzofuran-2-carboxylic acid 3-methyl-5-styryl-isoxazol-4-ylamide 
• 35351-21-4 5-bromo-2-carboxamidobenzo[b]furan 
• 1233086-56-0 C₂₁H₂₁F₂O₆P 

Relevant articles and documents

Enantiopure Benzofuran-2-carboxamides of 1-Aryltetrahydro-β-carbolines Are Potent Antimalarials In Vitro

The tetrahydro-β-carboline scaffold has proven fertile ground for the discovery of antimalarial agents (e.g., MMV008138 (1) and cipargamin (2)). Similarity searching of a publicly disclosed collection of antimalarial hits for molecules resembling 1 drew our attention to N2-acyl tetrahydro-β-carboline GNF-Pf-5009 ((±)-3b). Compound purchase, “analog by catalog”, and independent synthesis of hits indicated the benzofuran-2-yl amide portion was required for in vitro efficacy against P. falciparum. Preparation of pure enantiomers demonstrated the pharmacological superiority of (R)-3b. Synthesis and evaluation of D- and F-ring substitution variants and benzofuran isosteres indicated a clear structure-activity relationship. Ultimately (R)-3b was tested in Plasmodium berghei-infected mice; unfavorable physicochemical properties may be responsible for the lack of oral efficacy.

Novel oxindole/benzofuran hybrids as potential dual CDK2/GSK-3β inhibitors targeting breast cancer: design, synthesis, biological evaluation, and in silico studies

The serine/threonine protein kinases CDK2 and GSK-3β are key oncotargets in breast cancer cell lines, therefore, in the present study three series of oxindole-benzofuran hybrids were designed and synthesised as dual CDK2/GSK-3β inhibitors targeting breast cancer (5a–g, 7a–h, and 13a–b). The N1 -unsubstituted oxindole derivatives, series 5, showed moderate to potent activity on both MCF-7 and T-47D breast cancer cell lines. Compounds 5d–f showed the most potent cytotoxic activity with IC50 of 3.41, 3.45 and 2.27 μM, respectively, on MCF-7 and of 3.82, 4.53 and 7.80 μM, respectively, on T-47D cell lines, in comparison to the used reference standard (staurosporine) IC50 of 4.81 and 4.34 μM, respectively. On the other hand, the N1 -substituted oxindole derivatives, series 7 and 13, showed moderate to weak cytotoxic activity on both breast cancer cell lines. CDK2 and GSK-3β enzyme inhibition assay of series 5 revealed that compounds 5d and 5f are showing potent dual CDK2/GSK-3β inhibitory activity with IC50 of 37.77 and 52.75 nM, respectively, on CDK2 and 32.09 and 40.13 nM, respectively, on GSK-3β. The most potent compounds 5d–f caused cell cycle arrest in the G2/M phase in MCF-7 cells inducing cell apoptosis because of the CDK2/GSK-3β inhibition. Molecular docking studies showed that the newly synthesised N1 -unsubstituted oxindole hybrids have comparable binding patterns in both CDK2 and GSK-3β. The oxindole ring is accommodated in the hinge region interacting through hydrogen bonding with the backbone CO and NH of the key amino acids Glu81 and Leu83, respectively, in CDK2 and Asp133 and Val135, respectively, in GSK-3β. Whereas, in series 7 and 13, the N1 -substitutions on the oxindole nucleus hinder the compounds from achieving these key interactions with hinge region amino acids what rationalises their moderate to low anti-proliferative activity.

Benzofuranyl-2-imidazoles as imidazoline I2 receptor ligands for Alzheimer's disease

Recent findings unveil the pharmacological modulation of imidazoline I2 receptors (I2-IR) as a novel strategy to face unmet medical neurodegenerative diseases. In this work, we report the chemical characterization, three-dimensional quantitative structure-activity relationship (3D-QSAR) and ADMET in silico of a family of benzofuranyl-2-imidazoles that exhibit affinity against human brain I2-IR and most of them have been predicted to be brain permeable. Acute treatment in mice with 2-(2-benzofuranyl)-2-imidazole, known as LSL60101 (garsevil), showed non-warning properties in the ADMET studies and an optimal pharmacokinetic profile. Moreover, LSL60101 induced hypothermia in mice while decreased pro-apoptotic FADD protein in the hippocampus. In vivo studies in the familial Alzheimer's disease 5xFAD murine model with the representative compound, revealed significant decreases in the protein expression levels of antioxidant enzymes superoxide dismutase and glutathione peroxidase in hippocampus. Overall, LSL60101 plays a neuroprotective role by reducing apoptosis and modulating oxidative stress.

Enantioselective Synthesis of Five-Membered-Ring Atropisomers with a Chiral Rh(III) Complex

Axially chiral atropisomeric compounds are widely applied in asymmetric catalysis and medicinal chemistry, and efficient methods for their synthesis are in high demand. This applies in particular to atropisomers derived from five-membered aromatic rings because their lower barrier for rotation among the biaryl axis limits their asymmetric synthesis. We report here an enantioselective C-H functionalization method using our chiral RhJasCp complex for the synthesis of the biaryl atropisomer types that can be accessed from three different five-membered-ring heterocycles.

STAT3 PROTEIN DEGRADERS

The present disclosure provides compounds represented by Formulae I and IV: wherein R1a, R1b, R2a, R2b, A, E, QD, and QE are as defined in the specification, and the salts and solvates thereof. Compounds of Formula I are degraders of STAT3. Compounds of Formula IV are inhibitors of STAT3. STAT3 degraders and inhibitors are useful for the treatment of cancer and other diseases.

Vinylogous Elimination/C-H Functionalization/Allylation Cascade Reaction of Allenoate Adducts: Synthesis of Ring-Fused Dihydropyridinones

A palladium-catalyzed cascade reaction of β′-allenoate adducts with aryl/heteroaryl carboxamides through a vinylogous elimination/C-H functionalization/intramolecular allylation reaction sequence has been developed with high Z stereoselectivity. Various ring-fused dihydropyridinones bearing an α,β-unsaturated ester substituent are obtained. It is the first example of application of the allenoate adducts to C-H functionalization annulations as practical precursors of hard-to-get functionalized electron-deficient 1,3-butadienes. Using air as the terminal oxidant also shows a great advantage in environmental friendliness.

SMALL MOLECULE DEGRADERS OF STAT3

The present disclosure provides compounds represented by Formula I or Formula VIII: wherein R1a, R1b, M, A, E, QA, and QB are as defined in the specification, and the salts and solvates thereof. Compounds of Formula I are degraders of STAT3 or dedraders of STAT3 and STAT1. Compounds of Formula VIII are inhibitors of STAT3. STAT3 degraders and inhibitors are useful for the treatment of cancer and other diseases.

Efficient synthesis of a benzo[b]furan building block

Unexpected difficulty in the conversion of a bromobenzofuran to the corresponding formylbenzofuran led us to develop a new synthesis for 5-formylbenzo[b]furan-2-carbonitrile (1). Copyright