1178895-46-9

Upstream product

• 118-48-9 isatoic anhydride 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 3930-83-4 o-iodobenzamide 
• 28144-70-9 anthranilic acid amide 

Relevant academic research and scientific papers

Antioxidant and ros inhibitory activities of heterocyclic 2-aryl-4(3h)-quinazolinone derivatives

Background: Antioxidants are small molecules that prevent or delay the process of oxidations caused by highly reactive free radicals. These molecules are known for their ability to protect various cellular architecture and other biomolecules from oxidative stress and free radicals. Thus, antioxidants play a key role in the prevention of oxidative damages caused by highly reactive free radicals. Methods: In the present study, a series of previously synthesized heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 were screened for antioxidant activity by employing in vitro DPPH and superoxide anion radical scavenging activities. ROS inhibitory activities were also evaluated by serum-opsonized zymosan activated whole blood phagocytes and isolated neutrophils. Cytotoxicity studies were carried out by employing an MTT assay against the 3T3 cell line. Results: Most of the 2-aryl-4(3H)-quinazolinone derivatives showed potent antioxidant activities in superoxide anion radical scavenging assay with IC50 value ranging between 0.57 μM-48.93 μM, as compared to positive control quercetin dihydrate (IC50 = 94.1 ± 1.1 μM ). Compounds 5, 6, and 14 showed excellent activity in DPPH assay. Compounds 5-8, 12-15, 17, and 20 showed promising activities in the ROS inhibition assay. All compounds were found to be non-cytotoxic against the 3T3 cell line. Structure antioxidant activity has been established. Conclusion: It can be concluded that most of the heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 are identified as promising antioxidant agents that are capable of fighting against free radicals and oxidative stress. Thus, they can serve as a lead towards treating oxidative stress and related pathologies.

Simple preparation method of 4 (3H)-quinazolinone derivative

The invention provides a simple preparation method of a 4 (3H)-quinazolinone derivative, the 4 (3H)-quinazolinone derivative can be synthesized in one step in a mixed solvent from anthranilamide and an aldehyde as raw materials under the catalysis effects of an ion catalyst, due to the use of the mixed solvent, the 4 (3H)-quinazolinone derivative can be postprocessed only by washing with ethanol and drying, postprocessing steps are simplified, the purity of the product is improved, and meanwhile time is saved.

Yttrium nitrate catalyzed synthesis, photophysical study, and TD-DFT calculation of 2,3-dihydroquinazolin-4(1H)-ones

We have developed an efficient method of the synthesis of 2,3-dihydroquinazolin-4(1H)-one (DHQ) using yttrium nitrate catalyst at room temperature. The synthetic method is simple, convenient, and easy product isolation. Best results obtained in CH3CN, DMF, or water. The synthesized DHQ derivatives are found to be good fluorophores, and their characteristic photoluminescence properties are measured. Absorption and emission spectra of DHQ derivatives were recorded in CH3CN. Calculated emission and absorption bands are in excellent agreement with experimentally observed values.

Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones

An efficient and practical copper-catalyzed consecutive synthesis of quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones from easily available 2-halobenzamides (or 2-halonicotinamides), aldehydes, and sodium azide has been developed, which gave the corresponding target products in 50-95% yields for 29 examples. This remarkable consecutive process involved sequential copper-catalyzed SNAr, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy for bioactive molecules containing quinazolinone class skeletons.

In vitro antileishmanial activities of 2-aryl-4(3H)-quinazolinones

A series of synthetic 2-aryl-4(3H)-quinazolinones (1-25) was evaluated for in vitro antileishmanial activities against promastigotes of Leishmania major. Compound 1, with nitro group installed at C-4′, was found to be the most active analog having the IC50 value of 35.8 ± 0.1 μM against the standard, pentamidine (IC50 = 5.09 ± 0.09 μM). Fourteen other derivatives i.e. 2, 5-8, 10-12, 14, 16, 19, 22, 24, ad 25, showed a moderate to weak antilieshmanial activity with IC50 values between 62.8-90.45 μM. The results indicate the potential of these compounds as leads for further studies towards the development of antileishmanial drugs.

2-Arylquinazolin-4(3H)-ones: A novel class of thymidine phosphorylase inhibitors

Thymidine phosphorylase (TP) over expression plays an important role in several pathological conditions, such as rheumatoid arthritis, chronic inflammatory diseases, psoriasis, and tumor angiogenesis. In this regard, a series of twenty-five 2-arylquinazolin-4(3H)-one derivatives 1-25 were evaluated for thymidine phosphorylase inhibitory activity. Six compounds 5, 6, 20, 2, 23, and 3 were found to be active against thymidine phosphorylase enzyme with IC50 values in the range of 42.9-294.6 μM. 7-Deazaxanthine (IC50 = 41.0 ± 1.63 μM) was used as a standard inhibitor. Compound 5 showed a significant activity (IC50 = 42.9 ± 1.0 μM), comparable to the standard. The enzyme kinetic studies on the most active compounds 5, 6, and 20 were performed for the determination of their modes of inhibition, and dissociation constants Ki. All active compounds were found to be largely non-cytotoxic against the mouse fibroblast 3T3 cell line. This study identifies a novel class of thymidine phosphorylase inhibitors which may be further investigated as leads to develop therapeutic agents.

QUINAZOLINES AS B-GLUCURONIDASE NOVEL INHIBITORS

Quinazoline derivatives 1-25, (2-[3,4-bis(methyloxy)phenyl]quinazolin-4-(3H)-one) and 2-[2-(ethyloxy)phenyl]quinazoline-4-(3H)-one) are reported as β-glucuronidase inhibitors useful in the treatment of β-glucuronidase hyperactivity disorders.

Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones

2-Arylquinazolin-4(3H)-ones 1-25 were synthesized by reacting anthranilamide with various benzaldehydes using CuCl2·2H 2O as a catalyst in ethanol under reflux. Synthetic 2-arylquinazolin-4(3H)-ones 1-25 were evaluated for their β-glucuronidase inhibitory potential. A trend of inhibition IC50 against the enzyme in the range of 0.6-198.2 μM, was observed and compared with the standard d-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM). Compounds 13, 19, 4, 12, 14, 22, 23, 25, 15, 8, 17, 11, 21, 1, 3, 18, 9, 2, and 24 with the IC50 values within the range of 0.6-44.0 μM, indicated that the compounds have superior activity than the standard. The compounds showed no cytotoxic effects against PC-3 cells. A structure-activity relationship is established.

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.