7033-50-3

Usage

Biological activities

anti-inflammatory, anti-cancer, insecticidal, anti-fungal
Potential agricultural applications
Potential in the development of new drugs for various diseases

Upstream product

• 108-24-7 acetic anhydride 
• 635-21-2 5-chloroanthranilic acid 
• 5202-87-9 2-acetamido-5-chlorobenzoic acid 
• 201230-82-2 carbon monoxide 
• 63069-48-7 p-chloro-o-iodoaniline 

Downstream Products

• 102023-71-2 4-(6-chloro-2-methyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonic acid-[2]pyridylamide 
• 107919-09-5 4-(6-chloro-2-methyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonic acid thiazol-2-ylamide 
• 62175-53-5 5-(2-acetylamino-5-chloro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 34999-45-6 N-(4-chloro-2-(4-chlorobenzoyl)phenyl)acetamide 
• 34999-44-5 5-Chlor-2--4'-methoxy-benzophenon 
• 34999-43-4 N-(4-chloro-2-(4-methylbenzoyl)phenyl)acetamide 
• 34999-46-7 N-(2-(4-fluorobenzoyl)-4-chlorophenyl)acetamide 
• 2894-64-6 2-Acetamino-4-chloro-2'-methoxybenzophenone 
• 73268-16-3 5-chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzoic acid 
• 62492-51-7 2-Acetylamino-5-chlor-3'-methoxy-benzophenon 
• 963-33-7 6-chloro-2-methyl-3-o-tolyl-3H-quinazolin-4-one 
• 152909-08-5 2-amino-5-chloro-2',4',-6'-trimethoxybenzophenone 
• 152911-43-8 (2-amino-5-chlorophenyl)(2,3-dimethoxyphenyl)methanone 
• 406684-57-9 (2-amino-5-chloro-phenyl)-(2-methoxy-3-methyl-phenyl)-methanone 

Relevant academic research and scientific papers

Synthesis of 5-chloro-2-methyl-3-(5-methylthiazol-2-yl)-4(3H)-quinazolinone and related compounds with potential biological activity

Eight new 2-methyl-4(3H)-quinazolinones (8a-8d, 9c, 9d, 10c, 10d) with one or two chlorine atoms in the benzene ring and a 5-methyl-1,3-thiazol-2-yl, 4-methyl-1,3-thiazol-2-yl, and 5-ethyl-1,3,4-thiadiazol-2-yl substituent in position 3 of the heterocyclic ring were synthesized and characterized. The two step procedure (Scheme 1) utilizes chlorosubstituted anthranilic acids (3a-3d) and acetic anhydride as the starting materials, with the respective chlorosubstituted 2-methyl-4H-3,1-benzoxazin-4-ones (4a-4d) as the intermediates. The quinazoline derivatives were characterized by their melting points, elemental analyses and the mass, ultraviolet, infrared, and 1H and 13C nmr spectra. The new compounds are expected to be biologically active.

Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction

Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.

Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.

Synthesis and evaluation of anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities of some 3H-quinazolin-4-one derivatives

Some new 3H-quinazolin-4-one derivatives were synthesised and screened for anticancer, antiphospholipases, antiproteases, and antimetabolic syndrome activities. Compound 15d was more potent in reducing the cell viabilities of HT-29 and SW620 cells lines to 38%, 36.7%, compared to 5-FU which demonstrated cell viabilities of 65.9 and 42.7% respectively. The IC50 values of 15d were ～20?μg/ml. Assessment of apoptotic activity revealed that 15d decreased the cell viability by down regulating Bcl2 and BclxL. Moreover, compounds, 8j, 8d/15a/15e, 5b, and 8f displayed lowered IC50 values than oleanolic acid against proinflammatory isoforms of hGV, hG-X, NmPLA2, and AmPLA2. In addition, 8d, 8h, 8j, 15a, 15b, 15e, and 15f showed better anti-α-amylase than quercetin, whereas 8g, 8h, and 8i showed higher anti-α-glucosidase activity than allopurinol. Thus, these compounds can be considered as potential antidiabetic agents. Finally, none of the compounds showed higher antiproteases or xanthine oxidase activities than the used reference drugs.

Quinazolin-4(3H)-one-Based Hydroxamic Acids: Design, Synthesis and Evaluation of Histone Deacetylase Inhibitory Effects and Cytotoxicity

The present article describes the synthesis and biological activity of various series of novel hydroxamic acids incorporating quinazolin-4(3H)-ones as novel small molecules targeting histone deacetylases. Biological evaluation showed that these hydroxamic acids were potently cytotoxic against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI?H23, lung). Most compounds displayed superior cytotoxicity than SAHA (suberoylanilide hydroxamic acid, Vorinostat) in term of cytotoxicity. Especially, N-hydroxy-7-(7-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5b) and N-hydroxy-7-(6-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5c) (IC50 values, 0.10–0.16 μm) were found to be approximately 30-fold more cytotoxic than SAHA (IC50 values of 3.29–3.67 μm). N-Hydroxy-7-(4-oxoquinazolin-3(4H)-yl)heptanamide (5a; IC50 values of 0.21–0.38 μm) was approximately 10- to 15-fold more potent than SAHA in cytotoxicity assay. These compounds also showed comparable HDAC inhibition potency with IC50 values in sub-micromolar ranges. Molecular docking experiments indicated that most compounds, as represented by 5b and 5c, strictly bound to HDAC2 at the active binding site with binding affinities much higher than that of SAHA.

Discovery and development of extreme selective inhibitors of the ITD and D835Y mutant FLT3 kinases

Aberrant activation of FMS-like tyrosine receptor kinase 3 (FLT3) is implicated in the pathogenesis of acute myeloid leukemia (AML) in 20–30% of patients. In this study we identified a highly selective (phenylethenyl)quinazoline compound family as novel potent inhibitors of the FLT3-ITD and FLT3-D835Y kinases. Their prominent effects were confirmed by biochemical and cellular proliferation assays followed by mice xenograft studies. Our modelling experiments and the chemical structures of the compounds predict the possibility of covalent inhibition. The most effective compounds triggered apoptosis in FLT3-ITD AML cells but had either weak or no effect in FLT3-independent leukemic and non-leukemic cell lines. Our results strongly suggest that our compounds may become therapeutics in relapsing and refractory AML disease harboring various ITD and tyrosine kinase domain mutations, by their ability to overcome drug resistance.

Novel Hydroxamic Acid Incorporating Quinazolin-4(3H)-ones as Histone Deacetylase Inhibitors and Anticancer Composition Comprising the Same

The compound according HDAC(histone deacetylase) to the present -4(3H)- won invention can, be used as an active. ingredient of, a potent anticancer agent, HDAC since the compound according, to the present invention can be used. as, an active ingredient of a potent anticancer agent, since the compound. according to the present invention can be used as an active ingredient of a potent anticancer agent. (by machine translation)

Identification of N-{[6-chloro-4-(2,6-dimethoxyphenyl)quinazolin-2-yl]carbonyl}-l-leucine (NTRC-808), a novel nonpeptide chemotype selective for the neurotensin receptor type 2

Compounds acting via the GPCR neurotensin receptor type 2 (NTS2) display analgesic effects in relevant animal models. Using a pharmacophore model based on known NT receptor nonpeptide compounds, we screened commercial databases to identify compounds that

STYRYL QUINAZOLINE DERIVATIVES AS PHARMACEUTICALLY ACTIVE AGENTS

The present invention relates to styryl quinazoline derivatives of the general formula (I) and pharmaceutically acceptable solvates, hydrates, salts, regioisomeric and polymorphic forms thereof as well as pharmaceutical compositions containing at least on

Development of 2-(4-oxoquinazolin-3(4 H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis

InhA, the enoyl acyl carrier protein reductase of Mycobacterium tuberculosis (MTB) is an attractive target for developing novel anti-tubercular agents. Twenty eight 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives were synthesized and evaluated for their in vitro MTB InhA inhibition. Compounds were further evaluated for their in vitro activity against drug sensitive and resistant MTB strains and cytotoxicity against RAW 264.7 cell line. Compounds were docked at the active site of InhA to understand their binding mode and differential scanning fluorimetry was performed to ascertain their protein interaction and stability.