33017-86-6

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloro-2-mercaptoquinazolin-4(3H)-one is utilized as a key intermediate in the synthesis of various drugs and active pharmaceutical ingredients. Its unique structural features contribute to the development of novel drug candidates.
Used in Anticancer Research:
In the field of oncology, 7-chloro-2-mercaptoquinazolin-4(3H)-one is studied for its potential as an anticancer agent, targeting a range of malignancies. Its ability to modulate multiple signaling pathways and inhibit enzyme activity makes it a promising candidate for further research and development.
Used in Antiviral Applications:
7-Chloro-2-mercaptoquinazolin-4(3H)-one is also being investigated for its antiviral properties, offering a potential avenue for the treatment of viral infections and diseases.
Used in Antioxidant Formulations:
Given its antioxidant capabilities, 7-chloro-2-mercaptoquinazolin-4(3H)-one is considered for use in antioxidant formulations, which could have implications for the prevention and treatment of oxidative stress-related conditions.
Used in Enzyme Inhibition Studies:
7-chloro-2-mercaptoquinazolin-4(3H)-one's capacity to inhibit enzyme activity positions it as a candidate for use in studies aimed at understanding and potentially manipulating enzymatic processes in various diseases and conditions.

Upstream product

• 17356-08-0 thiourea 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 1147550-11-5 ammonium thiocyanate 
• 5900-58-3 2-amino-4-chloro-benzoic acid methyl ester 
• 342623-34-1 methyl 4-chloro-2-isothiocyanatobenzoate 

Downstream Products

• 19407-66-0 7-chloro-2-(4-methoxyphenyl)quinazolin-4(3H)-one 

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.

Conversion of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones by copper-mediated Pd-catalysed cross-coupling reactions

With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr·Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

An efficient ionic liquid mediated synthesis of substituted 5H[1,3]-thiazolo[2,3-b]quinazoline-3,5-(2H)-dione and 5H-thiazolo[2,3-b] quinazolin-5-one

A new, environmentally benign two-step synthesis of 5H[1,3]-thiazolo[2,3-b] quinazoline-3,5-(2H)-dione and 5H-thiazolo[2,3-b]quinazolin-5-one derivatives has been accomplished stepwise. The substituted 2-aminobenzoic acid upon condensation with thiourea in 1-butyl-3-methylimidazolium bromide at moderate temperature under nitrogen atmosphere yielded 2-thioxo-1H-4-quinazolinones. The resulting intermediate 2-thioxo-1H-4-quinazolinones, when reacted with 2-chloroethanoic acid/2-chloropropanal underwent cyclization to yield the desired product in excellent yields.