49681-96-1

Usage

Uses

Used in Pharmaceutical Research and Development:
6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE is used as a key intermediate in the synthesis of biologically active compounds for pharmaceutical applications. Its unique structure allows for the development of new drug candidates with potential therapeutic effects against various diseases.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE serves as a valuable building block for the creation of novel drug candidates. Its bromine atom and thioxo group can be further modified or used as starting points for the synthesis of more complex molecules with specific biological activities.
Used in Drug Design and Optimization:
6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE is utilized in drug design and optimization processes to improve the pharmacological properties of new compounds. Its unique structural features can be exploited to enhance the potency, selectivity, and pharmacokinetic properties of drug candidates, leading to more effective treatments for various diseases.
Used in Drug Discovery:
6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE plays a role in drug discovery, where it is screened for potential biological activities and evaluated for its ability to modulate specific biological targets. 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE can serve as a starting point for the identification of new therapeutic agents with novel mechanisms of action.
Used in Biochemical Research:
In biochemical research, 6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE can be employed as a tool compound to study the interactions between small molecules and biological macromolecules, such as enzymes, receptors, or nucleic acids. This information can be crucial for understanding the molecular mechanisms of diseases and for the development of targeted therapies.
Used in Chemical Synthesis:
6-BROMO-2-THIOXO-2,3-DIHYDROQUINAZOLIN-4(1H)-ONE is also used in chemical synthesis for the preparation of various quinazolinone-based derivatives with diverse chemical and biological properties. Its versatility as a synthetic building block contributes to the discovery of new chemical entities with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Preparation method of 2-thioxo-2,3-dihydroquinazoline-4(1H)-one compound

The invention discloses a preparation method of a 2-thioxo-2,3-dihydroquinazoline-4(1H)-one compound. The preparation method of the compound of formula I includes the following steps: a compound of formula II and a compound of formula III are subjected to a condensation reaction in an organic solvent under the action of an organic base to obtain the compound of the formula I, wherein the reactiontemperature is 70-155 DEG C, X1, X2, X3 and X4 are independently hydrogen or halogen, and R is hydrogen or one of alkyl groups of C1-C4. The preparation method provided by the invention is mild in conditions, environment-friendly, low in cost, high in yield, simple and efficient, and is suitable for industrial production. The formula of the reaction is shown in the description.

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.

GABAA RECEPTOR MODULATORS

the resent invention relates to novel compounds of the general formula (I) having anxiolytic, anticonvulsant, sedative-hypnotic and myorelaxant conditions as well as anxiogenic, somnolytic and convulsant conditions in mammals, including humans, as GABAA receptor modulator.

4,6-DL- AND 2,4,6-TRISUBSTITUTED QUINAZOLINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS USEFUL FOR TREATING VIRAL INFECTIONS

This invention provides the treatment of viral infections with a 4,6- disubstituted or 2,4,6-trisubstituted quinazoline derivative represented by the structural formula [(I)] wherein: R2 is selected from the group consisting of hydrogen, NR'R"

4,6-DL- AND 2,4,6-TRISUBSTITUTED QUINAZOLINE DERIVATIVES USEFUL FOR TREATING VIRAL INFECTIONS

This invention provides quinazoline derivatives represented by the structural formula: (I); wherein: R2 is hydrogen, NR'R", C1-7 alkyl, arylC1-7 alkyl or C3-10 cycloalkyl; R4 is amino, C1-7

Oxidative cyclocondensation of cyclic thio(seleno)ureas. 4. Electronic effects of the substituents and the medium

We have studied the electronic effect of substituents, steric factors, the medium, and the nature of the oxidizing agent on oxidative cyclocondensation of 2-thioxo-4-quinazolone and its substituted derivatives. We have found that electron-donor substituents promote the reaction while electronacceptor substituents inhibit the reaction. 2006 Springer Science+Business Media, Inc.

4,4-DISUBSTITUTED PIPERIDINE DERIVATIVES HAVING CCR3 ANTAGONISM

The invention provides low molecular compounds having activity which inhibits binding of CCR3 ligands to CCR3 on target cells, i.e. CCR3 antagonists. The invention also provides 4,4-(disubstituted)piperidine derivatives represented by formula (I) below, pharmaceutically acceptable acid adducts thereof, or pharmaceutically acceptable C1-C6 alkyl adducts thereof, as well as pharmaceutical compositions comprising them as effective ingredients, which are useful for treatment or prevention of diseases associated with CCR3, such as asthma and allergic rhinitis.

Synthesis of 2-aminoquinazoline-4(3H)-one derivatives as potential potassium channel openers

Starting from 2-thioxoquinazolin-4-one, the synthesis of 2-amino-4(3H)- one derivatives, structurally related to potassium channels openers pinacidil and diazoxide, is described.