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 
• 1222-20-4 N-(2-Carboxy-phenyl)-N'-phenyl-thioharnstoff 
• 75-15-0 carbon disulfide 
• 33800-08-7 1,3-Didehydro-2,1,3-benzothiadiazin-4-on 
• 62-53-3 aniline 
• 16024-82-1 methyl 2-isothiocyanatobenzoate 
• 4955-82-2 1-cyanothioformanilide 
• 17356-08-0 thiourea 

Downstream Products

• 83671-73-2 2-benzylthio-3-phenyl-4-oxo-3,4-dihydroquinazoline 
• 23285-07-6 bis(4-oxo-3-phenylquinazolin-2-yl) disulphide 
• 72033-78-4 3a-ethoxy-2,4-diphenyl-3a,4-dihydro-thiazolo[3,2-a]quinazoline-1,5-dione 
• 72033-77-3 1,5-dioxo-2,4-diphenyl-1,2-dihydro-5H-thiazolo[3,2-a]quinazolinium betaine 
• 144898-78-2 4-Oxo-3-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-4-p-tolyl-butyric acid 
• 28831-35-8 (3-phenyl-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetic acid ethyl ester 
• 144898-82-8 3-phenyl-2-thioureido-4(1H,3H)-quinazolone 
• 19062-39-6 3-amino-2-hydrazinoquinazolin-4(3H)-one 
• 95241-43-3 3-amino-2-(phenylamino)-4(3H)-quinazolinone 
• 731-52-2 2-hydrazino-3-phenyl-3H-quinazolin-4-one 
• 81262-71-7 2‐{[2‐oxo‐2‐(4‐phenylpiperazin‐1‐yl)ethyl]thio}‐3‐phenylquinazolin‐4(3H)‐one 
• 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 
• 130719-48-1 2-[2-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-oxo-ethylsulfanyl]-3-phenyl-3H-quinazolin-4-one 
• 84705-24-8 3a-Methoxy-4-phenyl-3a,4-dihydro-thiazolo[3,2-a]quinazoline-1,5-dione 

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, 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.