6484-23-7

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 28144-70-9 anthranilic acid amide 
• 100-43-6 4-vinylpyridine 
• 15854-87-2 4-iodopyridine 
• 201230-82-2 carbon monoxide 
• 1120-87-2 4-bromopyridin 

Downstream Products

• 6484-27-1 4-chloro-2-(pyridin-4-yl)quinazoline 
• 1448311-33-8 C₂₀H₁₅N₃O₃S 
• 157863-22-4 3-((2-(pyridin-4-yl)quinazolin-4-yl)amino)benzoic acid 

Relevant academic research and scientific papers

Method for synthesizing quinazolinone compound through visible light induction

The method is mild in reaction condition, simple and convenient in post-treatment operation, free of additional additives, high I in reaction efficiency, wide II in substrate adaptability, high in product purity, green and environment-friendly, and the method has III the advantages of mild reaction conditions, no need of additional additives, high reaction efficiency, wide substrate adaptability.

A Metal- and Ligand-Free Synthesis of Quinazolin-4(3H)-ones via a Bu4NI/TBHP-Mediated Oxidative Cleavage of the Olefinic C=C Bond

Abstract: A metal and ligand-free protocol has been developed for the synthesis of quinazolin-4(3H)-ones in moderate to good yields from o-aminobenzamide and alkenes via a Bu4NI/TBHP-mediated oxidative cleavage of the C=C bond in alkenes.

Discovery of Quinazolin-4(3 H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation

NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C-C triple/double bond and the release of formaldehyde. The reaction relies on the C-N bond formation along with the C-C bond cleavage under metal-free conditions. The nitro-substituted quinazolin-4(3H)-one 2k inhibited NLRP3 inflammasome (IC50 5 μM) via the suppression of IL-1β release from ATP-stimulated J774A.1 cells.

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones

The first heterogeneous carbonylative annulation of 2-aminobenzamides with aryl iodides was achieved in N,N-dimethylformamide (DMF) at 120 °C under 10 bar of carbon monoxide by using an MCM-41-immobilized bidentate phosphine palladium(II) complex [MCM-41-2P-Pd(OAc)2] as catalyst and 1,8-diazabicycloundec-7-ene (DBU) as base, yielding a wide variety of quinazolinone derivatives in good to excellent yields. The new heterogeneous palladium catalyst can easily be prepared by a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution, and recycled up to eight times without significant loss of activity.

The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

Performing any synthesis using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the orthoposition, successful chemical reactions could be performed due to intramolecular control. At maximum contact of the reacting substances, i.e., under solvent-free mechanochemical conditions, 2-aminobenzamides, aryl-, alkylaldehydes and the iodine(V) reagent o-iodoxybenzoic acid (IBX) led to substituted quinazolin-4(3H)-one derivatives in fair yields.

Synthesis and structure–activity relationship study of novel quinazolinone-based inhibitors of MurA

MurA is an intracellular bacterial enzyme that is essential for peptidoglycan biosynthesis, and is therefore an important target for antibacterial drug discovery. We report the synthesis, in silico studies and extensive structure–activity relationships of a series of quinazolinone-based inhibitors of MurA from Escherichia coli. 3-Benzyloxyphenylquinazolinones showed promising inhibitory potencies against MurA, in the low micromolar range, with an IC50 of 8?μM for the most potent derivative (58). Furthermore, furan-substituted quinazolinones (38, 46) showed promising antibacterial activities, with MICs from 1?μg/mL to 8?μg/mL, concomitant with their MurA inhibitory potencies. These data represent an important step towards the development of novel antimicrobial agents to combat increasing bacterial resistance.

4-Anilino-2-pyridylquinazolines and -pyrimidines as Highly Potent and Nontoxic Inhibitors of Breast Cancer Resistance Protein (ABCG2)

Multidrug resistance (MDR) mediated by ATP-binding cassette (ABC) transport proteins remains a major problem in the chemotherapeutic treatment of cancer and might be overcome by inhibition of the transporter. Because of the lack of understanding, the complex mechanisms involved in the transport process, in particular for breast cancer resistance protein (BCRP/ABCG2), there is a persistent need for studies of inhibitors of ABCG2. In this study, we investigated a systematic series of 4-substituted-2-pyridylquinazolines in terms of their inhibitory potency as well as selectivity toward ABCG2. For comparison, the quinazoline scaffold was reduced to the significantly smaller 4-methylpyrimidine basic structure. Furthermore, the cytotoxicity and the ability to reverse MDR was tested with the chemotherapeutic agents SN-38 and mitoxantrone (MX). Interaction of the compounds with ABCG2 was investigated by a colorimetric ATPase assay. Enzyme kinetic studies were carried out with Hoechst 33342 as fluorescent dye and substrate of ABCG2 to elucidate the compounds binding modes.

Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: Synthesis of natural products and drugs

A mild and greener protocol was developed to synthesize substituted quinazolinones and dihydroquinazolinones via deep eutectic solvent (DES) mediated cyclization with a series of aliphatic, aromatic, and heteroaromatic aldehydes in good to excellent yields. This greener strategy was further utilised to synthesize various quinazolinone natural products and drugs.

Palladium-catalyzed carbonylative synthesis of quinazolinones from 2-aminobenzamide and aryl bromides

C from CO! A straightforward procedure for the carbonylative synthesis of quinazolinones from readily available 2-aminobenzamide and aryl bromides has been developed. In the presence of a palladium catalyst, various quinazolinones were produced in moderate to excellent yields. Remarkably, no chromatography was needed for purification (see scheme). Copyright