99067-49-9

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
4(3H)-Quinazolinone,3-(chloromethyl)-(6CI) is used as a building block for the synthesis of novel compounds with potential therapeutic applications. Its chloromethyl group serves as a versatile handle for further chemical modifications, allowing for the development of new drugs with improved efficacy and safety profiles.
Used in Medicinal Chemistry:
4(3H)-Quinazolinone,3-(chloromethyl)-(6CI) is used as a promising candidate for further exploration in medicinal chemistry due to its quinazolinone core structure, which may possess interesting pharmacological properties. 4(3H)-Quinazolinone,3-(chloromethyl)-(6CI) can be studied and modified to develop new drugs with potential applications in various therapeutic areas.
Used in Chemical Synthesis:
4(3H)-Quinazolinone,3-(chloromethyl)-(6CI) is used as a valuable building block in the synthesis of novel compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique structural features and reactivity make it a useful intermediate in the development of new chemical entities.

Upstream product

• 118-92-3 anthranilic acid 
• 14663-52-6 3-(hydroxymethyl)quinazolin-4(3H)-one 
• 491-36-1 4-Hydroxyquinazoline 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

Synthesis and antibacterial evaluation of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety

A series of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety were synthesised and their antibacterial activities against tobacco and tomato bacterial wilts evaluated in vitro. Out of the synthesised compounds, 5g, 5j, 5n, 5m and 5p exhi

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.

4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives and preparation method thereof

The invention discloses 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives. The 4(3H)-quinazolinone-containing 1,4-pentadiene-3-ketoxime ether derivatives are characterized in that the general formula of the derivatives is described in the description, wherein R1 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R2 is phenyl, substituted phenyl or substituted aromatic heterocyclic group; R3 is one or more hydrogen atoms, methoxy group, nitro group, methyl group, trifluoromethyl group or halogen atoms contained in the 5, 6, 7 or 8 site of 4(3H)-quinazolinone. The compounds provided by the invention have higher treatment and protection functions for cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV), and shows better plant virus resisting activity, thus being used for preparing anti-plant-virus pesticides.

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.

[...] propoxycyclohexyl the pentadiene ketone compound, preparation method and application

The invention discloses a compound of resisting plant viruses: a pentadienone compound containing quinazolinone aryloxy and a preparation method and biological activity. The invention introduces a series of novel pentadienone derivatives containing quinazolinone aryloxy which are synthesized by six steps by taking substituted o-aminobenzoic acid, formamide, 35% formalin, 1, 4-dioxane, thionyl chloride, hydroxyl benzaldehyde, acetone, sodium hydroxide, hydrochloric acid, potassium carbonate, potassium iodide, substituted aromatic aldehyde, substituted heterocyclic aldehyde and the like as raw materials. The compound disclosed by the invention further has higher treating, protecting and passivating and inhibiting effects to cucumber mosaic virus (CMV), tobacco mosaic virus (TMV), southern rice black streaked dwarf virus (SRBSDV) and rice stripe virus (RSV), shows higher anti-plant virus activity, and can be used for preparing anti-plant virus pesticides.

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.

Synthesis and photophysical properties of N-styrylazinones

(Chemical Equation Presented) N-Styrylazinones and 1-styrylbenzotriazine were synthesized, and their photophysical properties were investigated. (Z)- and/or (E)-N-Styrylazinones (or azine) 4 were prepared from the corresponding heterocycles 1 and benzaldehyde (3) by four methods. The absorption maxima of (Z)- and/or (E)-4a - 4j were measured in four solvents. Their absorption maxima showed a moderate dependence upon solvents. The absorption maxima of (Z)-isomers were blue-shifted as compared the corresponding (E)-isomers. Emission maxima, fluorescence band half-widths, 0,0 transition energies, Stokes shifts, and quantum yields of (Z)- and/or (E)-4a, 4b, 4d, 4e and 4j were measured in organic solvents. The fluorescence spectra show moderate solvatochroism. The fluorescence properties of N-styrylheterocycles vary with every heterocycles.