31793-65-4

Upstream product

• 6141-13-5 2-chloroquinazoline 
• 62-53-3 aniline 
• 1173997-54-0 C₁₄H₁₅N₃S 
• 1010687-44-1 N-phenyl-1,4-dihydroquinazolin-2-amine 
• 607-68-1 2,4-dichloroquinazoline 
• 40138-16-7 2-formylbenzene boronic acid 
• 6685-76-3 phenylguanidinium hydrogencarbonate 

Relevant academic research and scientific papers

De novodesign and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions

Described here is thede novodesign and synthesis of a series of 6H-dipyrido[1,2-e:2′,1′-i]purin-6-ones (DPs) as a new class of visible-light photoredox catalysts (PCs). The synthesizedDP1-5showed theirλAbs(max)values in 433-477 nm, excited state redox potentials in 1.15-0.69 eV and ?1.41 to ?1.77 eV (vs.SCE), respectively. As a representative,DP4enables the productive guanylation of various amines, including 1°, 2°, and 3°-alkyl primary amines, secondary amines, aryl and heteroaryl amines, amino-nitrile, amino acids and peptides as well as propynylamines and α-amino esters giving diversities in biologically important guanidines and cyclic guanidines. The photocatalytic efficacy ofDP4in the guanylation overmatched commonly used Ir and Ru polypyridyl complexes, and some organic PCs. Other salient merits of this method include broad substrate scope and functional group tolerance, gram-scale synthesis, and versatile late-stage derivatizations that led to a derivative81exhibiting 60-fold better anticancer activity against Ramos cells with the IC50of 0.086 μM than that of clinical drug ibrutinib (5.1 μM).

2-Aminoquinazolines by Chan-Evans-Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids

A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan-Evans-Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines can be used as reactants to give the corresponding 2-aminoquinazolines in moderate yields from readily available (2-formylphenyl)boronic acids.

Discovery of 2-arylquinazoline derivatives as a new class of ASK1 inhibitors

The development of a new series of apoptosis signal-regulating kinase 1 (ASK1) inhibitors is described. Starting from purine, pyrimidine and quinazoline scaffolds identified by high throughput screening, we used tools of structure-based drug design to develop a series of potent kinase inhibitors, including 2-arylquinazoline derivatives 12 and 23, with submicromolar inhibitory activities against ASK1. Kinetic analysis demonstrated that the 2-arylquinazoline scaffold ASK1 inhibitors described herein are ATP competitive.

Ruthenium-Catalyzed para-Selective C?H Alkylation of Aniline Derivatives

The para-selective C?H alkylation of aniline derivatives furnished with a pyrimidine auxiliary is herein reported. This reaction is proposed to take place via an N?H-activated cyclometalate formed in situ. Experimental and DFT mechanistic studies elucidate a dual role of the ruthenium catalyst. Here the ruthenium catalyst can undergo cyclometalation by N?H metalation (as opposed to C?H metalation in meta-selective processes) and form a redox active ruthenium species, to enable site-selective radical addition at the para position.

Nucleophilic aromatic substitution of heterocycles using a high-temperature and high-pressure flow reactor

We report herein a high-temperature and high-pressure continuous-flow protocol to carry out nucleophilic aromatic substitution (SNAr) of heterocycles with nitrogen nucleophiles. Utilizing the Phoenix Flow Reactor in parallel with Design-of-Experiment software enabled rapid optimization of the SNAr protocol. This protocol facilitated efficient synthesis of a broad range of 2-aminoquinazolines, and was extended to 2-aminoquinoxalines and 2-aminobenzimidazoles.

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.

2-Chloroquinazoline. Synthesis and reactivity of a versatile heterocyclic building block

Starting from 2,4-dichloroquinazoline, various methods for the selective removal of the 4-chloro substituent were tested, including catalytic hydrogenation, metal-halogen exchange, metal hydride reduction and reduction with tributyltin hydride-the latter