18741-24-7

Basic information

• Product Name: 3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE
• Synonyms: TIMTEC-BB SBB000936;1,3-dihydro-3-phenyl-2-thio-quinazolin-4-on;3-PHENYL-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE;3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE;AKOS BBS-00007268;2,3-dihydro-3-phenyl-2-thioxoquinazolin-4(1H)-one;3-Phenyl-1,2,3,4-tetrahydro-2-thioxoquinazolin-4-one;3-Phenyl-2-thioxo-1,2,3,4-tetrahydroquinazolin
• CAS NO: 18741-24-7
• Molecular Formula: C₁₄H₁₀N₂OS
• Molecular Weight: 254.31
• EINECS: 242-550-6
• Product Categories: quinazolinone
• Mol File: 18741-24-7.mol
• Article Data: 76

Chemical Properties

• Melting Point: 313-314°C
• Boiling Point: 414.8 °C at 760 mmHg
• Flash Point: 204.6 °C
• Appearance: /
• Density: 1.4 g/cm³
• PKA: 10.96±0.20(Predicted)
• CAS DataBase Reference: 3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE(18741-24-7)
• EPA Substance Registry System: 3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE(18741-24-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 18741-24-7(Hazardous Substances Data)

Usage

General Description

3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE is a chemical compound with a molecular formula C15H11N3OS. It is a quinazolinone derivative with a thioxo group attached to the 2-position and a phenyl group at the 3-position. 3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE has potential pharmaceutical applications due to its structural similarities to other biologically active molecules. It may exhibit pharmacological effects such as antimicrobial, antiviral, or antitumor activities, and further research is needed to fully understand its potential uses. Additionally, its unique structure makes it of interest to medicinal chemists for the development of novel drugs.

InChI:InChI=1/C14H10N2OS/c17-13-11-8-4-5-9-12(11)15-14(18)16(13)10-6-2-1-3-7-10/h1-9H,(H,15,18)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 118-92-3 anthranilic acid 
• 134-20-3 2-carbomethoxyaniline 
• 2209-59-8 1,6-diphenyl-dithiodiurea 
• 7341-63-1 1-allyl-3-phenyl-thiourea 
• 103-85-5 monophenylthiourea 
• 118-48-9 isatoic anhydride 
• 17356-08-0 thiourea 
• 62-53-3 aniline 
• 56624-42-1 methyl 3-((phenylcarbamothioyl)thio)propanoate 
• 28144-70-9 anthranilic acid amide 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 43009-16-1 phenyldithiocarbamic acid triethylamine salt 
• 75-15-0 carbon disulfide 

Downstream Products

• 84705-24-8 3a-Methoxy-4-phenyl-3a,4-dihydro-thiazolo[3,2-a]quinazoline-1,5-dione 
• 84705-23-7 3a-Ethoxy-4-phenyl-3a,4-dihydro-thiazolo[3,2-a]quinazoline-1,5-dione 
• 87439-73-4 2‐[(4‐oxo‐3‐phenyl‐3,4‐dihydroquinazolin‐2‐yl)thio]‐Nphenylacetamide 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 2401-00-5 3-phenyl-2,3-dihydro-4(1H)-quinazolinone 
• 117038-34-3 3-phenyl-2-(2-pyridylmethylthio)-4-oxo-3,4-dihydroquinazoline 
• 18619-72-2 2-(2-diethylamino-ethylsulfanyl)-3-phenyl-3H-quinazolin-4-one 
• 56670-94-1 2-(1H-benzoimidazol-2-ylmethylsulfanyl)-3-phenyl-3H-quinazolin-4-one 
• 105471-50-9 copper(II)(PQT)2(pyridine)2 
• 25303-41-7 Cu(C₆H₄CON(C₆H₅)CSN)2 

Relevant articles and documents

Design and synthesis of novel 3-(phenyl)-2-(3-substituted propylthio) quinazolin-4-(3H)-ones as a new class of H1-antihistaminic agents

A series of novel 3-(phenyl)-2-(3-substituted propylthio) quinazolin-4-(3H)-ones were synthesized by the reaction of 2-(3-bromopropylthio)-3-(phenyl) quinazolin-4-(3H)-one with various amines. The starting material, 2-(3-bromopropylthio)-3-(phenyl) quinazolin-4-(3H)-one was synthesized from aniline. When tested for their in vivo H1-antihistaminic activity on conscious guinea pigs, all the test compounds protected the animals from histamine-induced bronchospasm significantly. Compound 2-(3-(4-methylpiperazin-1-yl) propylthiothio)-3- (phenyl) quinazolin-4(3H)-one (Ph5) emerged as the most active compound (73.23% protection) of the series when compared with the reference standard chlorpheniraminemaleate (70.09% protection). Compound Ph5 shows negligible sedation (5.01 %) compared with chlorpheniramine maleate (29.58%). Therefore, compound Ph5 can serve as the leading molecule for further development into a new class of H1-antihistaminic agents.

Synthesis and pharmacological evaluation of some 3-phenyl-2-substituted-3H-quinazolin-4-one as analgesic, anti-inflammatory agents

A variety of novel 3-phenyl-2-substituted-3H-quinazolin-4-ones were synthesized by reacting the amino group of 2-hydrazino-3-phenyl-3H-quinazolin-4-one with different aldehydes and ketones. The starting material 2-hydrazino-3-phenyl-3H-quinazolin-4-one was synthesized from aniline. The title compounds were investigated for analgesic, anti-inflammatory and ulcerogenic index activities. While the test compounds exhibited significant activity, compounds, 2-(N′-2-butylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS1), 2-(N′-3-pentylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS2) and 2-(N′-2-pentylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS3), exhibited moderate analgesic activity. The compound 2-(N′-2-pentylidene-hydrazino)-3-phenyl-3H-quinazolin-4-one (AS3) showed more potent anti-inflammatory activity when compared to the reference standard diclofenac sodium. Interestingly, the test compounds showed only mild ulcerogenic side effect when compared to aspirin.

Nanomolar and selective determination of epinephrine in the presence of norepinephrine using carbon paste electrode modified with carbon nanotubes and novel 2-(4-oxo-3-phenyl-3,4-dihydroquinazolinyl)-n′-phenyl- hydrazinecarbothioamide

A novel modified carbon nanotube paste electrode of 2-(4-oxo-3-phenyl-3,4- dihydro-quinazolinyl)-N′-phenyl-hydrazinecarbothioamide (2PHC) was fabricated, and the electrooxidation of epinephrine (EP), norepinephrine (NE), and their mixture has been studied using electrochemical methods. The modified electrode displayed strong catalytic function for the oxidation of EP and NE and resolved the overlap voltammetric response of EP and NE into two well-defined voltammetric peaks of about 240 mV with square wave voltammetry (SWV). A linear response in the range of (5 × 10-8)-(5.5 × 10 -4) M with a detection limit (S/N = 3) of 9.4 nM for EP was obtained.

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.