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

• 701-73-5 methyl N-phenyldithiocarbamate 
• 134-20-3 2-carbomethoxyaniline 
• 62-53-3 aniline 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 118-48-9 isatoic anhydride 
• 103-72-0 phenyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 118-92-3 anthranilic acid 
• 16024-82-1 methyl 2-isothiocyanatobenzoate 
• 33800-08-7 1,3-Didehydro-2,1,3-benzothiadiazin-4-on 
• 103-85-5 monophenylthiourea 
• 7341-63-1 1-allyl-3-phenyl-thiourea 
• 2209-59-8 1,6-diphenyl-dithiodiurea 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 

Downstream Products

• 130719-49-2 2-[2-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-methyl-2-oxo-ethylsulfanyl]-3-phenyl-3H-quinazolin-4-one 
• 87439-50-7 2-(Carbethoxypropylthio)-4(3H)-quinazolone 
• 86148-91-6 o-Tolyloxy-thioacetic acid S-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl) ester 
• 86148-92-7 p-Tolyloxy-thioacetic acid S-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl) ester 
• 86148-90-5 (2-Chloro-phenoxy)-thioacetic acid S-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl) ester 
• 80416-42-8 1-(3-Methoxy-phenyl)-3-[2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetyl]-urea 
• 87439-75-6 N-(4-Hydroxy-phenyl)-2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide 
• 80416-41-7 1-(2-Methoxy-phenyl)-3-[2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetyl]-urea 
• 129579-63-1 3-(4-Oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanylcarbonyl)-propionic acid (3S,8S,9S,10R,13R,14S,17R)-17-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 130719-50-5 2-[1-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carbonyl)-propylsulfanyl]-3-phenyl-3H-quinazolin-4-one 
• 117038-96-7 2-[1-Diethylaminomethyl-2-(2-oxo-pyrrolidin-1-yl)-ethylsulfanyl]-3-phenyl-3H-quinazolin-4-one; hydrochloride 
• 117038-99-0 2-[2-(2-Oxo-pyrrolidin-1-yl)-1-piperidin-1-ylmethyl-ethylsulfanyl]-3-phenyl-3H-quinazolin-4-one; hydrochloride 
• 117039-05-1 2-[1-Azepan-1-ylmethyl-2-(2-oxo-pyrrolidin-1-yl)-ethylsulfanyl]-3-phenyl-3H-quinazolin-4-one; hydrochloride 
• 117063-97-5 2-[1-Morpholin-4-ylmethyl-2-(2-oxo-pyrrolidin-1-yl)-ethylsulfanyl]-3-phenyl-3H-quinazolin-4-one; hydrochloride 

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.

Synthesis, in vitro, and in silico studies of newly functionalized quinazolinone analogs for the identification of potent α-glucosidase inhibitors

Functionalized quinazolinone derivatives 1–30 were synthesized by two-step reaction. First, anthranilic acid was treated with substituted phenyl isothiocyanate to synthesize 3-aryl-2-thioxo-2,3-dihydroquinazolinone derivatives 1–8 which in turn reacted with different bromoacetophenone derivatives to obtain fully functionalized quinazolinone derivatives 9–30. Both reactions were catalyzed by triethylamine. All the products were characterized by EI-, HREI-MS, 1H-, and 13CNMR spectroscopic techniques. All compounds were subjected to their in vitro α-glucosidase inhibitory activity. Results showed that except compound 1–3, 5, 7, and 22, all compounds were found potent and showed many folds increased α-glucosidase enzyme inhibition as compared to standard acarbose (IC50 = 750.0 ± 10.0?μM). Compound 13 (IC50 = 85.0 ± 0.5?μM) was recognized as the most potent analog of the whole series, with ninefold enhanced inhibitory potential than the standard acarbose. Compounds 1–9, 11, 12, 22, and 26 were structurally known compounds, while remaining all are new. Kinetic study on compound 13 showed that the compound is following a competitive-type inhibition mechanism. Furthermore, in silico studies have also been performed to better rationalize the interactions between synthetic compound and active site of the enzyme. Graphic abstract: [Figure not available: see fulltext.]