13906-09-7

Basic information

• Product Name: 2-MERCAPTO-4(3H)-QUINAZOLINONE
• Synonyms: 2-MERCAPTO-4(3H)-QUINAZOLINONE;2-MERCAPTOQUINAZOLIN-4(3H)-ONE;2-MERCAPTOQUINAZOLIN-4-ONE;2-THIO-4(3H)-QUINAZOLINONE;2,3-dihydro-2-thioxoquinazolin-4(1H)-one;1,2,3,4-Tetrahydro-2-thioxoquinazoline-4-one;2,3-Dihydro-2-thioxo-4(1H)-quinazolinone;2-Mercapto-4-quinazolinol
• CAS NO: 13906-09-7
• Molecular Formula: C₈H₆N₂OS
• Molecular Weight: 178.21
• EINECS: 237-676-3
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinazolines
• Mol File: 13906-09-7.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 330.5°Cat760mmHg
• Flash Point: 153.7°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 0.000165mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: 2-8°C
• PKA: 9.49±0.20(Predicted)
• CAS DataBase Reference: 2-MERCAPTO-4(3H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MERCAPTO-4(3H)-QUINAZOLINONE(13906-09-7)
• EPA Substance Registry System: 2-MERCAPTO-4(3H)-QUINAZOLINONE(13906-09-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 13906-09-7(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2-Mercapto-4(3H)-quinazolinone is used as a modifier for the carbon paste electrode for the voltammetric determination of mercury. Its unique chemical properties allow for the selective and sensitive detection of mercury ions, making it a valuable tool in environmental and industrial monitoring.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Mercapto-4(3H)-quinazolinone is used in the synthesis of 4-quinazolinone derivatives, which are known to be inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase (PARP). These derivatives have potential applications in the development of anticancer drugs, as they can help in the treatment of various types of cancer by targeting the DNA repair mechanisms in cancer cells.
Used in Material Science:
The FTIR and FT-Raman spectra of 2-mercapto-4(3H) quinazolinone have been studied, which provides insights into its molecular structure and vibrational modes. This information can be useful for understanding its interactions with other molecules and its potential use in the development of new materials.
Used in Chemical Synthesis:
Alkylation of 2-mercapto-4(3H)-quinazolinone has been reported, which demonstrates its reactivity and potential for further chemical modifications. This property can be exploited in the synthesis of new compounds with diverse applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C8H6N2OS/c11-7-5-3-1-2-4-6(5)9-8(12)10-7/h1-4H,(H2,9,10,11,12)

Upstream product

• 118-92-3 anthranilic acid 
• 77287-34-4 formamide 
• 5993-69-1 quinazolin-2,4(1H, 3H)-dithione 
• 491-36-1 4-Hydroxyquinazoline 
• 81511-63-9 2-(N-phenyl carboxamidomethyl thio)-5-phenyl-1,3,4-oxadiazole 
• 13277-24-2 N-benzoyl-N'-(2-carboxyphenyl)thiourea 
• 16182-04-0 Ethoxycarbonyl isothiocyanate 
• 23051-17-4 2-thioureido-benzoic acid ethyl ester 
• 115271-80-2 2-(Thioureido)benzoic acid methyl ester 
• 50440-89-6 4-amino-1H-quinazoline-2-thione 
• 23051-21-0 ethylanthranilatethiocyanate 
• 75-15-0 carbon disulfide 
• 28144-70-9 anthranilic acid amide 
• 463-71-8 thiophosgene 

Downstream Products

• 6437-06-5 2-(methylsulfanyl)-3-methyl-quinazolin-4(3H)-one 
• 23905-59-1 3-Phenyl-5-oxo-5H-thiazolo<2,3-b>chinazolin 
• 90852-43-0 C₁₇H₁₆N₂OS 
• 6344-77-0 2-(benzylsulfanyl)quinazolin-4(3H)-one 
• 16822-65-4 2-(4-methylpiperazin-1-yl)quinazolin-4(3H)-one 
• 139047-57-7 3-bromomethyl-5-methylthio-2,3-dihydroimidazo[1,2-c ]quinazoline 
• 6956-60-1 2-butyl thioquinazolin-4(3H)-one 
• 130719-44-7 2-[1-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonyl)-propylsulfanyl]-3H-quinazolin-4-one 
• 119023-30-2 2-<3-<3-(1-piperidinylmethyl)phenoxy>propylthio>-4(3H)-quinazolinone hydrochloride 
• 54855-81-1 2-methylthioquinazolin-4(3H)-one 
• 491-36-1 4-Hydroxyquinazoline 
• 86-96-4 1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 1134436-20-6 2-[(3,4-dihydroxy-5-methoxyphenyl)thio]quinazolin-4(3H)-one 
• 1134436-18-2 2-[(4,5-dihydroxy-2-methylphenyl)thio]quinazolin-4(3H)-one 

Relevant articles and documents

Synthesis of heterocycles via enamines-XIII1 1 H. Singh, S. Kumar, J. Chem. Soc., Perkin Trans 1, 1987, in press. Steric control on the mode of reactions of β-isothiocyanatoketones with amino-acids

Glycine and anthranilic acid with 4-isothiocyanato-butan-2-one (1) gives 3-(3-oxobutyl)-4-oxoimidazolidine-2-thione (11) and 3-(3-oxobutyl)-2-thioxoquinazolin-4-one (15) whereas with 4-isothiocyanato-4-methylpentan-2-one (2), having a gem-dimethyl group at the carbon bearing isothiocyanate group, tetrahydro-7,7,8a-trimethyl-5-thioxo-6H-oxazolo[3,2-c] pyrimidine-2(3H)-one (14) and 2,3,4,4a-tetrahydro-3,3,4a-trimethyl-1-thioxo-1H,6H-pyrimido[1,6a][3,1]-benzoxazin-6-one (17) are formed.

SYNTHESIS AND ALKYLATION OF 2-MERCAPTO-4-QUINAZOLONE AND THE FUNGICIDAL ACTIVITIES OF THE COMPOUNDS OBTAINED

A convenient method of obtaining 2-mercapto-4-quinazolone has been developed and the alkylation of its ambidentate anions has been studied.It has been found that they exhibit a dual reactivity in alkylation reactions.It has been shown that alkylated 2-mercapto-4-quinazolones possess a moderate fungicidal activity.

Synthesis, Cytotoxic Activity Evaluation of Novel 1,2,3-Triazole Linked Quinazoline Derivatives

A series of novel 1,2,3-triazole-quinazoline derivatives were synthesized in five steps starting from anthranilamide by conventional methods. All the title compounds 10a—10r were evaluated for cytotoxic activity against four human cancer cell lines (MGC-803, EC-109, MCF-7 and HGC-27) using MTT assay in vitro. Some of the synthesized compounds exhibited moderate to potent activity against tested cancer cell lines. Among them, compounds 10 h and 10q exhibited excellent growth inhibition against HGC-27 and compound 10 m also possessed excellent activity against MCF-7, with IC50 values less than 1 μmol/L. Especially, compound 10 h was more cytotoxic than 5-fluorouracil against all tested four human cancer cell lines.

2-Mercapto-Quinazolinones as Inhibitors of Type II NADH Dehydrogenase and Mycobacterium tuberculosis: Structure-Activity Relationships, Mechanism of Action and Absorption, Distribution, Metabolism, and Excretion Characterization

Mycobacterium tuberculosis (MTb) possesses two nonproton pumping type II NADH dehydrogenase (NDH-2) enzymes which are predicted to be jointly essential for respiratory metabolism. Furthermore, the structure of a closely related bacterial NDH-2 has been reported recently, allowing for the structure-based design of small-molecule inhibitors. Herein, we disclose MTb whole-cell structure-activity relationships (SARs) for a series of 2-mercapto-quinazolinones which target the ndh encoded NDH-2 with nanomolar potencies. The compounds were inactivated by glutathione-dependent adduct formation as well as quinazolinone oxidation in microsomes. Pharmacokinetic studies demonstrated modest bioavailability and compound exposures. Resistance to the compounds in MTb was conferred by promoter mutations in the alternative nonessential NDH-2 encoded by ndhA in MTb. Bioenergetic analyses revealed a decrease in oxygen consumption rates in response to inhibitor in cells in which membrane potential was uncoupled from ATP production, while inverted membrane vesicles showed mercapto-quinazolinone-dependent inhibition of ATP production when NADH was the electron donor to the respiratory chain. Enzyme kinetic studies further demonstrated noncompetitive inhibition, suggesting binding of this scaffold to an allosteric site. In summary, while the initial MTb SAR showed limited improvement in potency, these results, combined with structural information on the bacterial protein, will aid in the future discovery of new and improved NDH-2 inhibitors.

2,4-Disubstituted quinazolines targeting breast cancer cells via EGFR-PI3K

A series of novel 2,4-disubstituted quinazolines were synthesized and evaluated for their anti-tumor activity against five human cancer cells (MDA-MB-231, MCF-7, PC-3, HGC-27 and MGC-803) using MTT assay. Among them, compound 9n showed the most potent cytotoxicity against breast cancer cells. Compound 9n also significantly inhibited the colony formation and migration of MDA-MB-231 and MCF-7 cells. Meanwhile, compound 9n induced cell cycle arrest at G1 phase and cell apoptosis, as well as increased accumulation of intracellular ROS. Furthermore, compound 9n exerted anti-tumor effects in vitro via decreasing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 9n markedly decreased p-EGFR and p-PI3K expression, which revealed that compound 9n targeted breast cancer cells via interfering with EGFR-PI3K signaling pathway. Molecular docking suggested that compound 9n could indeed bind into the active pocket of EGFR. All the findings suggest that compound 9n might be a valuable lead compound for anti-tumor agents targeting breast cancer cells.

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.

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.

Preparation method and application of quinazolinone derivatives containing disulfide structure

The present invention relates to a class of disulfide-containing structure of quinazoline ketone derivative preparation method and application thereof. The compound having a structure as shown in formula (I): The present invention takes quinazolinone as the parent structure, the dishioalkyl (heterocyclic) structure is introduced into this system, a series of quinazolineone derivatives containing disulfide structure are synthesized, the series of compounds has a good inhibitory effect on plant pathogenic pathogenic bacteria, such as rice leaf blight, citrus canker fungus, kiwi canker bacteria and solanum subtilis and solanum subtilis.

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.

1,2,3-Triazole structure unit-containing 2,4-disubstituted quinazoline compounds, and preparation method and use thereof

The invention belongs to the technical field of pharmaceutical chemistry synthesis, and discloses 1,2,3-triazole structure unit-containing 2,4-disubstituted quinazoline compounds, and a preparation method and a use thereof. A series of 1,2,3-triazole structure unit-containing 2,4-disubstituted quinazoline compounds are prepared from anthranilamide through cyclization, substitution, chlorination and aminolysis reactions. The compounds have a structure represented by general formula I. Preliminary in vitro antitumor activity evaluation finds that the series of the compounds have obvious inhibiting and killing effects on various tumor cells. The compounds can be processed to develop new medicines, and can be applied to clinic prevention and cancer treatment as an active component.