18741-24-7

Usage

Uses

Used in Pharmaceutical Industry:
3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE is used as a potential pharmaceutical agent for its possible antimicrobial, antiviral, or antitumor activities. Its structural similarities to biologically active molecules suggest that it may exhibit therapeutic effects against various diseases and conditions.
Used in Medicinal Chemistry Research:
3-PHENYL-2-THIOXO-1,2,3,4-TETRAHYDROQUINAZOLIN-4-ONE is used as a starting point for the development of novel drugs by medicinal chemists. Its unique structure and potential pharmacological effects make it an interesting compound for further research and exploration in the field of drug discovery and design.

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 
• 18741-28-1 2-(2',3'-dihydroxypropylthio)-3-phenyl-4(3H)-quinazolinone 
• 57266-65-6 3-phenyl-hexahydro-quinazoline-2,4-dione 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 2401-00-5 3-phenyl-2,3-dihydro-4(1H)-quinazolinone 

Relevant academic research and scientific papers

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 Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N -(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds

Ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4) with thiocarbonyl-bis-thioglycolic acid gave a new compound name N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide (5). Knoevenagel condensation of (5) with appropriate aldehydes gave fourteen (Z)-N-(5-arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide compounds (6a-o) with moderate yield. The chemical structure of the compounds was elucidated on the basis of IR, 1H-NMR, 13C-NMR, and HR-MS spectral data. The 5-arylidene-2-thioxothiazolidinone compounds exhibited mild-to-moderate cytotoxic activity against both K562 (chronic myelogenous leukemia) cells and MCF7 (breast cancer) cells.

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.

Synthesis, Spectroscopic Characterization, and Time-Dependent DFT Calculations of 1-Methyl-5-phenyl-5H-pyrido[1,2-a]quinazoline-3,6-dione and Its Starting Precursor in Different Solvents

In this study, 2-mercapto-3-phenyl-2,3-dihydro-1H-quinazolin-4-one (1), which exists as a thiol and thione tautomer, was treated with acetylacetone to give the target compound, namely, 1-methyl-5-phenyl-5H-pyrido[1,2-a]quinazoline-3,6-dione (2). The spectroscopic data, including UV/Vis, IR, 1H NMR, 13C NMR, and mass data, of this compound were recorded. The molecular structures of the starting material (1) and the product (2) were optimized by using density functional theory (DFT) by employing the B3LYP exchange correlation with the 6-311G (d, p) and 6-31G++ (d, p) basis sets. The electronic spectra were determined based on time-dependent DFT calculations in three different solvents (i.e., chloroform, ethanol, and acetonitrile) starting from the same solvated run of the optimized geometry with the same two basis sets. The solvent effects were considered based on the polarizable continuum model (PCM), and the energetic behavior of the compounds and the total static dipole moment (μ) in different solvents were examined in the two basis sets; the results showed that the total energy of the compounds decreased upon increasing the polarity of the solvent. Time-dependent DFT calculations were performed to analyze the electronic transitions for various excited states that reproduced the experimental band observed in the UV/Vis spectrum. A study on the electronic properties, such as the HOMO and LUMO energies, was performed by the time-independent DFT approach. Using the gauge-independent atomic orbital method (GIAO), the 1H NMR chemical shifts were calculated and correlated with the experimental ones. The computed results showed that the introduction of different dielectric media had a slight effect on the stability and reactivity of the title compound as well as on the Milliken atomic charges and the molecular geometry. Besides, the molecular electrostatic potential of target product 2 was evaluated in different solvents.

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.

Synthesis and biological evaluation of some 3H-quinazolin-4-one derivatives

Starting from 3-phenylquinazoline-2,4(1H,3H)-dithione, some new derivatives of 3H-quinazoline-4-ones were synthesized. The structures of all new compounds were inferred based on the mass spectral, infrared, and NMR spectral data as well as the elemental analytical data. Some compounds were chosen for testing their biological activities as antibacterial, antifungal, and anticancer agents. Graphic abstract: [Figure not available: see fulltext.]

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.]

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.

2-HETEROARYL AMINOQUINAZOLINONE DERIVATIVE

Provided is a 2-heteroaryl aminoquinazolinone derivative, which is a compound represented by formula (1): or a pharmaceutically acceptable salt thereof wherein X1 represents CR1 or N, X2 represents CR2 or N, X3 represents CR3 or N, X4 represents CR4 or N, Y represents optionally substituted C1-6 alkyl, an optionally substituted C3-10 alicyclic group, an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle, optionally substituted C6-10 aryl, or optionally substituted 5- to 10-membered heteroaryl, Z represents optionally substituted 6- to 10-membered heteroaryl, and R1, R2, R3, and R4 each independently represent a hydrogen atom, halogen, cyano, optionally substituted C1-6 alkyl, optionally substituted C1-6 alkoxy, or the like.