14663-52-6

Basic information

• Product Name: 3-(Hydroxymethyl)quinazolin-4(3H)-one
• Synonyms: 3-(Hydroxymethyl)quinazolin-4(3H)-one;3-(HydroxyMethyl)-4(3H)-quinazolinone
• CAS NO: 14663-52-6
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.17202
• EINECS: -0
• Mol File: 14663-52-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 364.9°Cat760mmHg
• Flash Point: 174.5°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 5.75E-06mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 3-(Hydroxymethyl)quinazolin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Hydroxymethyl)quinazolin-4(3H)-one(14663-52-6)
• EPA Substance Registry System: 3-(Hydroxymethyl)quinazolin-4(3H)-one(14663-52-6)

Safety Data

• Hazardous Substances Data: 14663-52-6(Hazardous Substances Data)

Usage

General Description

3-(Hydroxymethyl)quinazolin-4(3H)-one is a chemical compound with the formula C9H8N2O2. It is a quinazolinone derivative, which means it is a member of the quinazolinone family of compounds. The "3-(Hydroxymethyl)" in its name indicates the presence of a hydroxymethyl group, which is a functional group consisting of a hydroxyl group (-OH) bonded to a methyl group (-CH2-). 3-(Hydroxymethyl)quinazolin-4(3H)-one has potential biological and pharmaceutical significance due to its quinazolinone scaffold, which is known to exhibit various pharmacological activities. Its synthesis and potential applications in medicinal chemistry make it a topic of interest for researchers in the pharmaceutical and chemical industries.

InChI:InChI=1/C9H8N2O2/c12-6-11-5-10-8-4-2-1-3-7(8)9(11)13/h1-5,12H,6H2

Upstream product

• 491-36-1 4-Hydroxyquinazoline 
• 50-00-0 formaldehyd 
• 118-92-3 anthranilic acid 

Downstream Products

• 99067-49-9 3-(chloromethyl)-3H-quinazolin-4-one 

Relevant articles and documents

First Report on Anti-TSWV Activities of Quinazolinone Derivatives Containing a Dithioacetal Moiety

Tomato spotted wilt virus (TSWV) is a plant virus with strong infectivity and destructive power. Given the lack of effective control agents, TSWV causes significant economic damage to several vegetables and ornamental plants worldwide. In this study, we designed and synthesized a series of novel quinazolinone derivatives containing a dithioacetal moiety and evaluated their antiviral activity in vitro and in vivo against TSWV. Some candidate compounds showed good anti-TSWV activity. Compound 6n shows excellent anti-TSWV activity in vivo, and the EC50 value is 188 mg/L, which is notably better than that observed for ribavirin (642 mg/L), xiangcaoliusuobingmi (420 mg/L), and ningnanmycin (257 mg/L). In addition, compound 6n interacts with TSWV coat protein at sites ARG94 and ARG95 forming four π-alkyl interactions. Compound 6n (9.4 μM) shows a better binding affinity with TSWV coat protein than ribavirin (67.8 μM), xiangcaoliusuobingmi (33.8 μM), and ningnanmycin (24.3 μM). Therefore, compound 6n can serve as a lead compound for the discovery of new antiviral agents for the management of TSWV.

Synthesis, antiviral activity, 3D-QSAR, and interaction mechanisms study of novel malonate derivatives containing quinazolin-4(3H)-one moiety

A series of novel malonate derivatives containing quinazolin-4(3H)-one moiety were synthesized and evaluated for their antiviral activities against cucumber mosaic virus (CMV). Results indicated that the title compounds exhibited good antiviral activities. Notably, compounds g15, g16, g17, and g18 exhibited excellent curative activities in vivo against CMV, with 50% effective concentration (EC50) values of 208.36, 153.78, 181.47, and 164.72 μg/mL, respectively, which were better than that of Ningnanmycin (256.35 μg/mL) and Ribavirin (523.34 μg/mL). Moreover, statistically valid three-dimensional quantitative structure-activity relationship (3D-QSAR) models with good correlation and predictive power were obtained with comparative molecular field analysis (CoMFA) steric and electrostatic fields (r2 = 0.990, q2 = 0.577) and comparative molecular similarity indices analysis (CoMSIA) with combined steric, electrostatic, hydrophobic and hydrogen bond acceptor fields (r2 = 0.977, q2 = 0.516), respectively. Based on those models, compound g25 was designed, synthesized, and showed better curative activity (146.30 μg/mL) than that of compound g16. The interaction of between cucumber mosaic virus coat protein (CMV CP) and g25 with 1:1.83 ratio is typically spontaneous and exothermic with micromole binding affinity by isothermal titration calorimetry (ITC) and fluorescence spectroscopy investigation.

Synthesis and antiviral bioactivity of novel 3-((2-((1 E,4 E)-3-Oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3 H)-quinazolinone derivatives

A series of novel 3-((2-((1E,4E)-3-oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone derivatives were designed and synthesized. Antiviral bioassays indicated that a few of the compounds exhibited higher antiviral activities against tobacco mosaic virus (TMV) in vivo than the commercial agent ningnanmycin. In particular, compounds A5, A12, A25, and A27possessed appreciable curative bioactivities on TMV in vivo, with 50% effective concentration values ranging from 132.25 to 156.10 μg/mL. These values are superior to that of ningnanmycin (281.22 μg/mL) and suggest that novel 4(3H)-quinazolinone derivatives containing 1,4-pentadien-3-one moiety can effectively control TMV. Evaluation of the antiviral properties in field studies and the mechanisms underlying the enhanced antiviral activities of these derivatives are an interesting topic for future investigation.