1035-51-4

Basic information

• Product Name: 3-(4-ETHOXYPHENYL)-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE
• Synonyms: 3-(4-ETHOXYPHENYL)-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE;3-(4-Ethoxyphenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one;3-(4-Ethoxyphenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
• CAS NO: 1035-51-4
• Molecular Formula: C₁₆H₁₄N₂O₂S
• Molecular Weight: 298.35956
• Mol File: 1035-51-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: >250
• Boiling Point: 475.2 °C at 760 mmHg
• Flash Point: 241.2 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 3.4E-09mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(4-ETHOXYPHENYL)-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-ETHOXYPHENYL)-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(1035-51-4)
• EPA Substance Registry System: 3-(4-ETHOXYPHENYL)-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE(1035-51-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 1035-51-4(Hazardous Substances Data)

Usage

General Description

3-(4-Ethoxyphenyl)-2-thioxo-2,3-dihydro-4(1H)-quinazolinone, also known as ETTQ, is a chemical compound with potential pharmaceutical applications. It belongs to the quinazolinone class of compounds and is characterized by the presence of a thioxo group and an ethoxyphenyl group. ETTQ has been studied for its potential as an anti-cancer agent, with research suggesting that it may have cytotoxic and anti-proliferative effects on cancer cells. Additionally, ETTQ has been investigated for its potential use as an anti-inflammatory and anti-bacterial agent. Its unique chemical structure and potential therapeutic properties make it a promising candidate for further research and development in the field of pharmaceutical chemistry.

InChI:InChI=1/C16H14N2O2S/c1-2-20-12-9-7-11(8-10-12)18-15(19)13-5-3-4-6-14(13)17-16(18)21/h3-10H,2H2,1H3,(H,17,21)

Upstream product

• 118-92-3 anthranilic acid 
• 3460-49-9 1-ethoxy-4-isothiocyanatobenzene 
• 75-15-0 carbon disulfide 
• 118-48-9 isatoic anhydride 
• 156-43-4 4-Ethoxyaniline 
• 4955-70-8 (4-ethoxyphenyl)carbamothioyl cyanide 

Downstream Products

• 108534-19-6 2-(2-Amino-ethylsulfanyl)-3-(4-ethoxy-phenyl)-3H-quinazolin-4-one 
• 108534-06-1 2-(3-Amino-propylsulfanyl)-3-(4-ethoxy-phenyl)-3H-quinazolin-4-one 
• 108534-41-4 2-(2-Diisopropylamino-ethylsulfanyl)-3-(4-ethoxy-phenyl)-3H-quinazolin-4-one 
• 105362-99-0 3-Amino-2-(4-ethoxy-phenylamino)-3H-quinazolin-4-one 
• 331972-16-8 2?((2?(4?chlorophenyl)?2?oxoethyl)thio)?3?(4?ethoxyphenyl)quinazolin?4(3H)?one 
• 105471-53-2 copper(II)(EPQT)2(pyridine)2 

Relevant articles and documents

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.

Identification of potent cholecystokinin-B receptor antagonists: Synthesis, molecular modeling and anti-cancer activity against pancreatic cancer cells

Advanced malignant stages of pancreatic cancer have poor prognosis and very few treatment strategies are available. Pancreatic cancer is known to possess unique growth-related receptors that when activated, stimulate tumour proliferation. Gastrin and its related peptide cholecystokinin (CCK) are also significantly involved in the growth of this cancer type as well as other malignancies through activation of the cholecystokinin-B receptor (CCK-BR). New treatment strategies with CCK-BR antagonists are being suggested that suppress the growth promoting effects of gastrin. In this paper, we report the development of two series of quinazolinone derivatives incorporating hydrazinecarbothioamide (compounds 3a-g) and the hydrazino group (compounds 4a-e) as linkers for developing CCK-BR antagonists. The affinities of the compounds were determined using docking into the CCK-BR homology modeled structure. The compounds were tested for in vitro CCK-BR binding and gastric acid secretion in an isolated lumen-perfused mouse stomach assay. The compounds exhibited CCK-BR binding activity (IC50) in the range of 0.2-975 nM and showed good gastric acid secretion inhibitory activity. Molecular modeling of the compounds was done and pharmacophore mapping results showed good prediction of in vitro activity which correlated well with the experimental antagonistic activity. The compounds were further tested for their cytotoxicity on CCK-BR expressing pancreatic cancer cells. The results of the study provided two potent CCK-BR antagonists which also possess good to moderate growth inhibitory activities against pancreatic cancer cells.

Some reactions with p-ethoxyphenylcyano-thioforamide: Synthesis of pyrrole, pyrrolo[2,3-c]pyrrole, imidazo[4,5-b]quinoxalines and hydantoin derivatives

P-Ethoxyphenylcyanothioformamide (1) was reacted with αβ-unsaturated ketone (2) and N-p-chlorophenylmaleimide (4) to furnish pyrrole and pyrrolo[2,3-c]pyrrol-4,6-diones (3) and (5) respectively. Also, interaction of 1 with anthranilic acid and o-phenylenediamine produced 3-(4′-ethoxyphenyl)-2-thioxoquinazolin-4-one (6) and 2-thioxobenzimidazoles (7). When, 1 was reacted with iso(thio)cyanates caused cyclization to afford 5-imino-4-thioxoimidazolidinones (9). Compound 9 was subjected to some reagents such as hydrazine hydrate, thiosemicarbazide, o-phenylenediamines, hydrogen sulfide and HCl to give 5-hydrazono, 4-thiosemicarbazono, and thiohydantoin derivatives (10-17), respectively.