17329-27-0

Usage

Uses

Used in Oncology:
2-(4-aminophenyl)quinazolin-4(1H)-one is used as a targeted therapy agent for the treatment of advanced or metastatic breast cancer. It is employed to inhibit the activity of EGFR and HER2, key drivers of cancer cell growth and proliferation, thereby slowing down or stopping the progression of the disease.
Used in Cancer Research:
In the field of cancer research, 2-(4-aminophenyl)quinazolin-4(1H)-one is used as a research tool to investigate the mechanisms of action of kinase inhibitors and their potential applications in the treatment of various solid tumors. This includes exploring its efficacy in combination with other therapeutic agents and understanding its impact on cancer cell signaling pathways.
Used in Drug Development:
2-(4-aminophenyl)quinazolin-4(1H)-one serves as a lead compound in the development of new anticancer drugs. Its structure and mechanism of action provide a foundation for the design of novel compounds that may exhibit improved potency, selectivity, or reduced side effects, ultimately contributing to the advancement of cancer therapeutics.

Upstream product

• 556-18-3 4-aminobenzaldehyde 
• 118-48-9 isatoic anhydride 
• 555-16-8 4-nitrobenzaldehdye 
• 28144-70-9 anthranilic acid amide 
• 277319-62-7 4-amino-N'-hydroxybenzimidamide 
• 873-74-5 4-Aminobenzonitrile 
• 1197-55-3 4-aminophenylacetic acid 

Downstream Products

• 701290-17-7 N-(4-(4-oxo-3,4-dihydroquinazoline-2-yl)phenyl)acetamide 

Relevant academic research and scientific papers

Quinazoline-4(3H)-one derivatives as novel and potent inhibitors of soluble epoxide hydrolase: Design, synthesis and biological evaluation

Inhibition of soluble epoxide hydrolase (sEH) is considered as a promising target to reduce blood pressure, improve insulin sensitivity, and decrease inflammation. In this study, a series of some novel quinazoline-4(3H)-one derivatives (3a-t) with varying steric and electronic properties was designed, synthesized and evaluated as sEH Inhibitors. Most of the synthesized compounds had similar inhibitory activity to the commercial reference inhibitor, 12-(3-adamantan-1-ylureido)dodecanoic acid, and amongst them, 4-chloro-N-(4-(4-oxo-3,4-dihydroquinazoline-2-yl)phenyl)benzamide (3g) was identified as the most active sEH inhibitor (IC50 = 0.5 nM), about 2-fold more potent compared to the reference inhibitor. The results of molecular modeling followed by biological studies indicate that a quinazolinone ring serves as a suitable scaffold to develop novel small molecule candidates to inhibit sEH and the nature of substituent on the amide moiety has a moderate effect on the activity.

An Efficient Synthesis of 2-Substituted Quinazolin-4(3H)-ones by Using Recyclable Wang Resin Supported Sulfonic Acid Catalyst

An efficient synthesis of 2-substituted Quinazolin-4(3H)-ones has been developed from isatoic anhydride with various amidoximes by using a recyclable polymer-supported sulphonic acid catalyst. Excellent functional group compatibility and high yields are the important features of this protocol.

Design, synthesis, and evaluation of HIV-1 entry inhibitors based on broadly neutralizing antibody 447-52D and gp120 V3loop interactions

The third variable loop region (V3 loop) on gp120 plays an important role in cellular entry of HIV-1. Its interaction with the cellular CD4 and coreceptors is an important hallmark in facilitating the bridging by gp41 and subsequent fusion of membranes for transfer of viral genetic material. Further, the virus phenotype determines the cell tropism via respective co– receptor binding. Thus, coreceptor binding motif of envelope is considered to be a potent anti-viral drug target for viral entry inhibition. However, its high variability in sequence is the major hurdle for developing inhibitors targeting the region. In this study, we have used an in silico Virtual Screening and “Fragment-based” method to design small molecules based on the gp120 V3 loop interactions with a potent broadly neutralizing human monoclonal antibody, 447-52D. From the in silico analysis a potent scaffold, 1,3,5-triazine was identified for further development. Derivatives of 1,3,5-triazine with specific functional groups were designed and synthesized keeping the interaction with co-receptor intact. Finally, preliminary evaluation of molecules for HIV-1 inhibition on two different virus strains (clade C, clade B) yielded IC50 5.0 μM. The approach used to design molecules based on broadly neutralizing antibody, was useful for development of target specific potent antiviral agents to prevent HIV entry. The study reported promising inhibitors that could be further developed and studied.

A in ammonia water condition of microwave halo benzoic acid synthesis method of the quinazoline compounds

The invention discloses a in ammonia water condition of microwave halo benzoic acid synthetic quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in ammonia water under the microwave heating condition, neighbouring halogen benzoic acid generated by the reaction with the isocyanate of the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.

A in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method

The invention discloses a in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in water under microwave heating conditions, neighbouring halogen benzamide with an isocyanate reaction to produce the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.

Structure-activity relationships of 2-arylquinazolin-4-ones as highly selective and potent inhibitors of the tankyrases

Tankyrases (TNKSs), members of the PARP (Poly(ADP-ribose)polymerases) superfamily of enzymes, have gained interest as therapeutic drug targets, especially as they are involved in the regulation of Wnt signalling. A series of 2-arylquinazolin-4-ones with varying substituents at the 8-position was synthesised. An 8-methyl group (compared to 8-H, 8-OMe, 8-OH), together with a 4′-hydrophobic or electron-withdrawing group, provided the most potency and selectivity towards TNKSs. Co-crystal structures of selected compounds with TNKS-2 revealed that the protein around the 8-position is more hydrophobic in TNKS-2 compared to PARP-1/2, rationalising the selectivity. The NAD+-binding site contains a hydrophobic cavity which accommodates the 2-aryl group; in TNKS-2, this has a tunnel to the exterior but the cavity is closed in PARP-1. 8-Methyl-2-(4-trifluoromethylphenyl)quinazolin-4-one was identified as a potent and selective inhibitor of TNKSs and Wnt signalling. This compound and analogues could serve as molecular probes to study proliferative signalling and for development of inhibitors of TNKSs as drugs.

Iron-catalyzed aerobic oxidative functionalization of sp3 C-H bonds: A versatile strategy for the construction of N-heterocycles

Iron-catalyzed aerobic oxidative functionalization of sp3 C-H bonds has been developed for the construction of N-heterocycles from easily available carboxylic acid derivatives and o-substituted anilines. This transformation represents a widely applicable protocol to N-heterocycles using biofriendly iron as a catalyst in combination with molecular oxygen or air as the sole oxidant. This journal is

An Efficient Synthesis of 2-Substituted Quinazolin-4(3 H)-ones Catalyzed by Iron(III) Chloride

A simple and highly efficient synthesis of 2-substituted quinazolin-4(3H)-ones by the iron(III) chloride catalyzed reaction of isatoic anhydride with various amidoxime derivatives was developed. Several aryl and alkyl amidoximes were screened to demonstra

TANKYRASE INHIBITORS

The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.

Computer-aided design, synthesis and validation of 2-phenylquinazolinone fragments as CDK9 inhibitors with anti-HIV-1 tat-mediated transcription activity

The activity of the cyclin-dependent kinase 9 (CDK9) is critical for HIV-1 Tat-mediated transcription and represents a promising target for antiviral therapy. Here we present computational studies that, along with preliminary synthetic efforts, allowed us