701290-17-7

Upstream product

• 118-48-9 isatoic anhydride 
• 122-85-0 para-acetamidobenzaldehyde 
• 16375-88-5 N-(4-hydroxymethylphenyl)acetamide 
• 28144-70-9 anthranilic acid amide 
• 17329-27-0 2-(4-aminophenyl)quinazoline-4(3H)-one 
• 555-16-8 4-nitrobenzaldehdye 
• 4765-59-7 2-(4-nitrophenyl)-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Amino acid-based ionic liquid immobilized on α-Fe2O 3-MCM-41: An efficient magnetic nanocatalyst and recyclable reaction media for the synthesis of quinazolin-4(3H)-one derivatives

For the first time, we report the synthesis and the application of magnetic nanocatalyst (α-Fe2O3)-MCM-41-l-prolinium nitrate which was characterized by XRD, TEM, IR, X-ray energy diffraction (XED) spectra and nitrogen physisorption measurements. l-prolinium nitrate (fully green amino acid-based ionic liquid) inside the mesochannels of (α-Fe 2O3)-MCM-41 lead to prepare a new solid catalyst which was used as an efficient heterogeneous catalyst for the one-pot oxidative cyclization straight synthesis of quinazolin-4(3H)-one derivatives from isatoic anhydride, aldehyde or alkyl halide and primary amines under mild reaction conditions without using any oxidant with good to excellent yields. Moreover, it was proven that in these reactions, the use of such a hybrid material as a catalyst plays the role of rendering the reactions while neither the (α-Fe2O3)-MCM-41 nor the l-prolinium nitrate were not able to promote this reaction in the desired pathway toward the above mentioned product. The characteristic features of this catalyst are attributed to both acidic and oxidative behavior of the catalyst.

A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones

In the present work, we report the design and fabrication of a copper-containing ionic liquid supported magnetic nanocatalyst via a convenient and straightforward synthetic approach for the formation of 2-phenylquinazolin-4(3H)-ones using o-aminobenzamide and benzaldehydes as the reaction partners. The successful formation and properties of the as-prepared catalyst have been thoroughly investigated using diverse physico-chemical techniques including FT-IR, XRD, FE-SEM, TEM, ICP, VSM, BET and TGA. Using this nanocatalytic system, a variety of 2-phenylquinazolin-4(3H)-ones are synthesized in excellent yields with operational ease and short reaction times in an environmentally preferable solvent under open air and without using any external oxidizing agent. Besides, the catalyst possessed facile magnetic recoverability and remarkable reusability for six consecutive runs without any appreciable decrease in the catalytic efficiency.

Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy

Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).

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.

Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes

An interesting procedure for the zinc-catalyzed oxidative transformation of ready available 2-aminobenzamide, 2-aminobenzenesulfonamide with benzyl alcohols has been developed. Various quinazolinones and benzothiadiazine 1,1-dioxides were prepared in moderate to good yields under identical conditions. The reactions of both aromatic aldehydes and aliphatic aldehydes with 2-aminobenzamide under catalyst free conditions were described as well. In water media, the products were formed in good yields.