331646-99-2

Basic information

• Product Name: 8-bromoquinazoline-2,4(1H,3H)-dione
• Synonyms: 8-bromoquinazoline-2,4(1H,3H)-dione;8-Bromo-2,4(1H,3H)-quinazolinedione;2,4(1H,3H)-Quinazolinedione, 8-bromo-;8-Bromo-1H-quinazoline-2,4-dione;8-BROMO-2,4-DIHYDROXY QUINOZALINE
• CAS NO: 331646-99-2
• Molecular Formula: C₈H₅BrN₂O₂
• Molecular Weight: 241.0415
• Mol File: 331646-99-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 537.6 °C at 760 mmHg
• Flash Point: 278.9 °C
• Appearance: /
• Density: 1.959 g/cm³
• Vapor Pressure: 3.58E-12mmHg at 25°C
• Refractive Index: 1.782
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.29±0.20(Predicted)
• CAS DataBase Reference: 8-bromoquinazoline-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 8-bromoquinazoline-2,4(1H,3H)-dione(331646-99-2)
• EPA Substance Registry System: 8-bromoquinazoline-2,4(1H,3H)-dione(331646-99-2)

Safety Data

• Hazardous Substances Data: 331646-99-2(Hazardous Substances Data)

Usage

General Description

8-Bromoquinazoline-2,4(1H,3H)-dione is a chemical compound with the molecular formula C8H5BrN2O2. It is a quinazoline derivative with a bromine atom attached to the 8-position and carbonyl groups at the 2 and 4 positions. 8-bromoquinazoline-2,4(1H,3H)-dione has been studied for its potential biological activities, including as an anticancer agent and for its inhibitory effects on certain enzymes. It has also been explored for its potential as a building block in the synthesis of other more complex organic compounds. Overall, 8-bromoquinazoline-2,4(1H,3H)-dione is a versatile chemical that has potential applications in both the pharmaceutical and chemical industries.

InChI:InChI=1/C8H5BrN2O2/c9-5-3-1-2-4-6(5)10-8(13)11-7(4)12/h1-3H,(H2,10,11,12,13)

Upstream product

• 20780-74-9 7-bromoisatin 
• 20776-51-6 2-amino-3-bromo benzoic acid 
• 917-61-3 sodium isocyanate 
• 608-30-0 2,6-dibromoaniline 
• 124-38-9 carbon dioxide 
• 114344-60-4 2-amino-3-bromo-benzonitrile 
• 57-13-6 urea 

Downstream Products

• 331647-05-3 8-bromo-2,4-dichloroquinazoline 
• 1262431-79-7 8-[(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]oxolan-2-yl]-2,4-dimethoxyquinazoline 

Relevant articles and documents

Discovery of (R)-8-(6-Methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4- b]pyrrol-2-yl)-3-(1-methylcyclopropyl)-2-((1-methylcyclopropyl)amino)quinazolin-4(3 H)-one, a Potent and Selective Pim-1/2 Kinase Inhibitor for Hematological Malignancies

Pim kinases are a family of constitutively active serine/threonine kinases that are partially redundant and regulate multiple pathways important for cell growth and survival. In human disease, high expression of the three Pim isoforms has been implicated in the progression of hematopoietic and solid tumor cancers, which suggests that Pim kinase inhibitors could provide patients with therapeutic benefit. Herein, we describe the structure-guided optimization of a series of quinazolinone-pyrrolodihydropyrrolone analogs leading to the identification of potent pan-Pim inhibitor 28 with improved potency, solubility, and drug-like properties. Compound 28 demonstrated on-target Pim activity in an in vivo pharmacodynamic assay with significant inhibition of BAD phosphorylation in KMS-12-BM multiple myeloma tumors for 16 h postdose. In a 2-week mouse xenograft model, daily dosing of compound 28 resulted in 33% tumor regression at 100 mg/kg.

Discovery of Quinazolines That Activate SOS1-Mediated Nucleotide Exchange on RAS

Proteins in the RAS family are important regulators of cellular signaling and, when mutated, can drive cancer pathogenesis. Despite considerable effort over the last 30 years, RAS proteins have proven to be recalcitrant therapeutic targets. One approach for modulating RAS signaling is to target proteins that interact with RAS, such as the guanine nucleotide exchange factor (GEF) son of sevenless homologue 1 (SOS1). Here, we report hit-to-lead studies on quinazoline-containing compounds that bind to SOS1 and activate nucleotide exchange on RAS. Using structure-based design, we refined the substituents attached to the quinazoline nucleus and built in additional interactions not present in the initial HTS hit. Optimized compounds activate nucleotide exchange at single-digit micromolar concentrations in vitro. In HeLa cells, these quinazolines increase the levels of RAS-GTP and cause signaling changes in the mitogen-activated protein kinase/extracellular regulated kinase (MAPK/ERK) pathway.

CONDENSED-RING PYRIMIDYLAMINO DERIVATIVE, PREPARATION METHOD THEREFOR, AND INTERMEDIATE, PHARMACEUTICAL COMPOSITION AND APPLICATIONS THEREOF

Disclosed are a condensed-ring pyrimidylamino derivative, a preparation method therefor, and an intermediate, a pharmaceutical composition and applications thereof. The method for preparing the condensed-ring pyrimidylamino derivative comprises: in a solvent, in the presence of a palladium-containing catalyst, allowing a compound represented by formula I-a and a compound represented by formula I-b' to have a coupling reaction, and then preparing a compound represented by formula I by means of a deprotection reaction. Also disclosed applications of the condensed-ring pyrimidylamino derivative in the preparation of drugs for preventing, relieving and/or treating tumors or diseases caused by an anaplastic lymphoma kinase. The condensed-ring pyrimidylamino derivative of the present invention has an obvious restraint effect on the anaplastic lymphoma kinase.