49681-96-1

Basic information

• Product Name: 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE
• Synonyms: 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE;6-bromo-2-mercaptoquinazolin-4-ol;6-bromo-2-mercaptoquinazolin-4(3H)-one
• CAS NO: 49681-96-1
• Molecular Formula: C8H5BrN2OS
• Molecular Weight: 257.1071
• Mol File: 49681-96-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 323-325 °C(Solv: water (7732-18-5))
• Appearance: /
• Density: 1.90±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 8.50±0.20(Predicted)
• CAS DataBase Reference: 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE(49681-96-1)
• EPA Substance Registry System: 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE(49681-96-1)

Safety Data

• Hazardous Substances Data: 49681-96-1(Hazardous Substances Data)

Usage

General Description

6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE is a chemical compound with the molecular formula C9H6BrN3OS. It is a derivative of quinazolinone, which is commonly used in medicinal chemistry for the synthesis of biologically active compounds. This specific compound has a bromine atom and a thioxo group attached to the quinazolinone ring, making it potentially useful in pharmaceutical research and development. The unique structure of 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE makes it a valuable building block for the creation of novel drug candidates and may have potential applications in the treatment of various diseases.

Upstream product

• 32084-59-6 6-bromoquinazolin-4(3H)-one 
• 1147550-11-5 ammonium thiocyanate 
• 52727-57-8 5-bromo-2-aminobenzoic acid methyl ester 
• 71860-11-2 7-bromo-5H-1,3,4-tiadiazolo<2,3-b>chinazolin-5-one 
• 4692-98-2 5-bromoisatoic anhydride 
• 17356-08-0 thiourea 
• 540-72-7 sodium thiocyanide 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 118-48-9 isatoic anhydride 
• 1189797-82-7 ethyl 6-bromo-4-oxo-2-thioxo-1,4-dihydroquinazoline-3(2H)-carboxylate 
• 1189797-80-5 5-bromo-2-({[(ethoxycarbonyl)amino]carbonothioyl}-amino)-benzoic acid 
• 1108665-60-6 2-amino-5-bromobenzoic acid chloride 
• 463-71-8 thiophosgene 
• 16313-66-9 5-bromoanthranilamide 

Downstream Products

• 174313-65-6 2-(methylsulfanyl)-6-bromo-quinazolin-4(3H)-one 
• 174313-65-6 6-bromo-2-(methylthio)-quinazolin-4-ol 

Relevant articles and documents

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

Triazoloquinazolinediones as novel high affinity ligands for the benzodiazepine site of GABAA receptors

Based on a pharmacophore model of the benzodiazepine-binding site of GABAA receptors, a series of 2-aryl-2,6-dihydro[1,2,4]triazolo[4,3-c] quinazoline-3,5-diones (structure type I) were designed, synthesized, and identified as high-affinity lig

A facile and convenient method to the one-pot synthesis of 2-mercapto-4(3H)-quinazolinones

A facile and convenient method to the one-pot synthesis of 2-mercapto-4(3H)-quinazolinones is described from the reaction of anthranilic acid derivatives with thiourea in PEG.