1028-40-6

Basic information

• Product Name: 3-(4-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE
• Synonyms: 3-(4-chlorophenyl)-2-sulfanylidene-1H-quinazolin-4-one;3-(4-chlorophenyl)-2-thioxo-1H-quinazolin-4-one;3-(4-Chlorophenyl)-2-thioxo-2,3-dihydro-4(1H)-quinazolinone;3-(4-chlorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one;4(1H)-Quinazolinone,3-(4-chlorophenyl)-2,3-dihydro-2-thioxo-
• CAS NO: 1028-40-6
• Molecular Formula: C₁₄H₉ClN₂OS
• Molecular Weight: 288.76
• Mol File: 1028-40-6.mol

Chemical Properties

• Boiling Point: 457.3°Cat760mmHg
• Flash Point: 230.4°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Refractive Index: 1.753
• CAS DataBase Reference: 3-(4-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE(1028-40-6)
• EPA Substance Registry System: 3-(4-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE(1028-40-6)

Safety Data

• Hazardous Substances Data: 1028-40-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
3-(4-Chloro-phenyl)-2-mercapto-3H-quinazolin-4-one is used as a precursor in the synthesis of therapeutic drugs for various medical applications. Its unique structure and chemical reactivity make it a promising candidate for the development of new pharmaceuticals.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3-(4-chloro-phenyl)-2-mercapto-3H-quinazolin-4-one is utilized as a key intermediate in the design and synthesis of novel compounds with potential therapeutic properties. Its chemical versatility allows for the exploration of various chemical modifications to enhance its pharmacological activity.
Used in Drug Discovery:
3-(4-chloro-phenyl)-2-mercapto-3H-quinazolin-4-one serves as a valuable tool in drug discovery processes. Its unique structural features and potential reactivity make it an attractive scaffold for the development of new drugs with improved efficacy and selectivity against specific targets.
Used in Biochemical Studies:
3-(4-CHLORO-PHENYL)-2-MERCAPTO-3H-QUINAZOLIN-4-ONE is also employed in biochemical studies to investigate its interactions with various biological macromolecules, such as proteins and nucleic acids. Understanding these interactions can provide insights into its potential therapeutic mechanisms and help guide the optimization of its chemical structure for specific applications.

InChI:InChI=1/C14H9ClN2OS/c15-9-5-7-10(8-6-9)17-13(18)11-3-1-2-4-12(11)16-14(17)19/h1-8H,(H,16,19)

Upstream product

• 118-48-9 isatoic anhydride 
• 106-47-8 4-chloro-aniline 
• 17356-08-0 thiourea 
• 705-69-1 N-(4-chlorophenyl)-S-methyldithiocarbamate 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 
• 3696-23-9 N-(4-chlorophenyl)thiourea 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 2314-48-9 (S,S)-dimethyl trithiocarbonate 
• 75-15-0 carbon disulfide 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 43009-19-4 p-chlorophenyldithiocarbamic acid triethylamine salt 
• 2400-95-5 3-(4-chlorophenyl)-1H,3H-quinazolin-2,4-dione 
• 610-94-6 2-bromobenzoic acid methyl ester 

Downstream Products

• 108534-17-4 2-(2-Amino-ethylsulfanyl)-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 108534-26-5 2-(3-Amino-propylsulfanyl)-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 108534-08-3 3-(4-Chloro-phenyl)-2-(2-diisopropylamino-ethylsulfanyl)-3H-quinazolin-4-one 
• 95241-44-4 3-amino-2-[(4-chlorophenyl)amino]-4(3H)-quinazolinone 
• 23224-99-9 3,3'-bis-(4-chloro-phenyl)-3H,3'H-2,2'-disulfanediyl-bis-quinazolin-4-one 
• 24122-31-4 3-(4-chlorophenyl)quinazolin-4(3H)-one 
• 2401-09-4 3-(4-chloro-phenyl)-2,3-dihydro-1H-quinazolin-4-one 
• 1031-97-6 2-methylsulfanyl-3-(4-chlorophenyl)-3H-quinazolin-4-one 
• 68357-61-9 1-methyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 67811-54-5 4-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 85772-57-2 1-ethyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 85772-64-1 1-chloromethyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 85772-62-9 1-propyl-4-(4-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 66679-74-1 2-hydrazino-3-(4-chlorophenyl)quinazoline-4(3H)-one 

Relevant articles and documents

Practical approach to 2-thioxo-2,3-dihydroquinazolin-4(1H)-one via dithiocarbamate–anthranilic acid reaction

A practical and straightforward protocol has been developed for the preparation of 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives from dithiocarbamate chemistry. The method involves the reaction of anthranilic acid derivatives (2-aminobenzoic acid, 2-aminobenzamide and isatoic anhydride) with various dithiocarbamate derivatives using ethanol as solvent. The main advantages of this protocol include practical simplicity, good to high yields, and ease of product isolation, purification and cheapness of the solvent.

An efficient one-pot procedure for preparation of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinone derivatives under microwave irradiation

An efficient one-pot synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinone derivatives are given by the condensation of isatoic anhydride, primary amine and urea or thiourea in the absence of organic or inorganic reagents under microwave irr

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives

A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.

CuBr-catalysed one-pot multicomponent synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives

A novel methodology is presented for the synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives based on an efficient tandem multicomponent reaction using copper bromide as catalyst. This methodology is based on the multicomponent one-pot reaction of methyl 2-bromobenzoate, phenylisothiocyanate derivatives and sodium azide in the presence of copper bromide and l-proline under basic conditions. To show the generality of the method, various phenylisothiocyanates bearing electron-donating or electron-withdrawing functionalities were used and the desired products were obtained in high isolated yields.

Design, synthesis, biological evaluation, and molecular docking study of thioxo-2,3-dihydroquinazolinone derivative as tyrosinase inhibitors

Tyrosinase is known to be a key enzyme in melanogenesis and hyperpigmentation. In this study, a series of thioxo-dihydroquinazolinone compounds were designed and synthesized as tyrosinase inhibitors. Among the investigated compounds, 4m demonstrated the best inhibitory activity with an IC50 value of 15.48 μM compared to kojic acid as a positive control with IC50 value of 9.30 μM. In kinetic evaluation against tyrosinase, 4m depicted a mixed inhibition pattern. Additionally, antioxidant evaluations exhibited moderate to weak potency in 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The detailed interactions and binding mode toward tyrosinase of the most potent derivative were explicated by molecular docking study. Moreover, the computer-aided drug-likeness and pharmacokinetic studies were also carried out.

Design and synthesis of novel quinazolinone-based fibrates as PPARα agonists with antihyperlipidemic activity

Aiming to discover new antihyperlipidemic agents, a new set of quinazolinone-fibrate hybrids 9a–r bearing the essential features for peroxisome proliferator-activated receptor-α (PPARα) agonistic activity was synthesized and the structures were confirmed by different spectral data. All the target compounds were screened for their PPARα agonistic activity. Compounds 9o and 9q exhibited potent activity, with EC50 values better than that of fenofibrate by 8.7- and 27-fold, respectively. Molecular docking investigations were performed for all the newly synthesized compounds in the active site of the PPARα receptor to study their interactions and energies in the receptor. Moreover, the antihyperlipidemic and antioxidant activities of compounds 9o and 9q were determined using Triton WR-1339-induced hyperlipidemic rats. Compound 9q exhibited effective hypolipidemic activity in a dose-dependent manner, where it significantly reduced the serum levels of total cholesterol, triglycerides, low-density lipoprotein cholesterol, and very-low-density lipoprotein cholesterol and increased the level of high-density lipoprotein cholesterol. Furthermore, it possesses a powerful antioxidant profile where it significantly elevated the levels of reduced glutathione as well as the total antioxidant capacity and significantly decreased the malondialdehyde level. The histopathological studies revealed that compound 9q improved the aortic architecture and hepatic steatosis. These findings support that compound 9q could be a promising lead compound for the development of new antihyperlipidemic agents.

Synthesis, biological evaluation and molecular docking studies of novel quinazolinones as antitubercular and antimicrobial agents

In the present study, a series of novel quinazolinone hybrids, viz. triazepino-quinazolinones 4, thiazolo-triazolo-quinazolinones 7 and triazolo-quinazolinones 8 have been synthesized from the key intermediate 3-(substituted phenyl)-2-hydrazinoquinazolin-4(3H)-ones 3. All the newly synthesized compounds were characterized by means of spectral (IR, 1H NMR, 13C NMR) and elemental analysis. The target compounds were biologically screened for their in vitro antimicrobial and antitubercular activities against pathogenic strain. The results of bioassay demonstrated that some of the compounds exhibited pronounced antimicrobial activity comparable to that of standard drugs tested under similar conditions. Compounds 4c, 4e, 7e and 8b showed relatively very good inhibitory activity against pathogenic bacteria with minimum inhibitory concentration (MIC) of 2.6 μg/mL, 5.2 μg/mL, while the rest of the compounds showed moderate activity. Compounds 4c and 8b were found to be nearly equipotent with ciprofloxacin against P. aeruginosa with MIC 5.2 μg/mL, while compound 8b was more potent against pathogenic bacteria S. aureus. It is very remarkable that four compounds, 4c, 4e, 7e and 8b showed pronounced antifungal activity against selected pathogenic fungi, A. niger, C. albicans with MIC 2.6 μg/mL and 5.2 μg/mL. The antitubercular activity of synthesized compounds reveal that compound 8b showed better activity than the other compounds with a MIC of 5.2 μg/mL against M. tuberculosis (H37Rv). Molecular docking studies of the compounds were performed to rationalize the inhibitory properties of these compounds and results showed that these compounds have good binding energy and better binding affinity within the active pocket, thus these compounds may be considered as potent inhibitors towards selective targets.

The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity

Melanin pigment and melanogenesis are a two-edged sword. Melanin has a radioprotection role while melanogenesis has undesirable effects. Targeting the melanogenesis pathway, a series of kojyl thioether conjugated to different quinazolinone derivatives were designed, synthesized, and evaluated for their inhibitory activity against mushroom tyrosinase. All the synthesized compounds were screened for their anti-tyrosinase activity and all derivatives displayed better potency than kojic acid as the positive control. In this regard, 5j and 5h as the most active compounds showed an IC50 value of 0.46 and 0.50 μM, respectively. In kinetic evaluation against tyrosinase, 5j depicted an uncompetitive inhibition pattern. Designed compounds also exhibited mild antioxidant capacity. Moreover, 5j and 5h achieved good potency against the B16F10 cell line to reduce the melanin content, whilst showing limited toxicity against malignant cells. The proposed binding mode of new inhibitors evaluated through molecular docking was consistent with the results of structure–activity relationship analysis.

Anti-HIV and Antibacterial Activities of Novel 2-(3-Substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones

Abstract: In the present study, we have synthesized a series of novel 2-(3-substituted-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-diones by the reaction of 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones with phthalic anhydride. The starting material 3-(substituted)-2-hydrazino-quinazolin-4(3H)-ones were synthesized from various primary amines. All the synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different gram positive and gram negative strains by agar dilution method. Among the test compounds, 2-(3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-2,3-dihydrophthalazine-1,4-dione (QCT7) shown most potent antibacterial activity against E. coli, and S. aureus with the MIC of 3 μg/mL. The compound QCT7 exhibited the antitubercular activity with the MIC of 25 μg/mL and anti-HIV activity with the EC50 of 43.68 μM against HIV1 and HIV2 and offers potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.