53449-14-2

Usage

Chemical Properties

Yellow or light yellow powder

InChI:InChI=1/C8H4ClN3O3/c9-5-2-6-4(1-7(5)12(14)15)8(13)11-3-10-6/h1-3H,(H,10,11,13)

Upstream product

• 31374-18-2 7-chloro-3,4-dihydroquinazolin-4-one 
• 100948-85-4 4-chloro-5-nitroanthranilic acid 
• 149-73-5 trimethyl orthoformate 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 31374-18-2 7-chloroquinazolin-4(1H)-one 
• 7664-93-9 sulfuric acid 
• 74-11-3 para-chlorobenzoic acid 
• 6280-88-2 4-chloro-2-nitro-benzoic acid 
• 5900-59-4 2-amino-4-chlorobenzamide 

Downstream Products

• 105664-93-5 6-nitro-7(methylamino)quinazolin-4(3H)-one 
• 53449-26-6 7-benzylamino-6-nitro-3H-quinazolin-4-one 
• 16292-86-7 2-hydroxy-4-amino-1-nitrobenzene 
• 5131-58-8 2,4-diaminonitrobenzene 
• 81946-23-8 2,4-diamino-5-nitro-benzoic acid 
• 53449-16-4 7-amino-6-nitroquinazolin-4(3H)-one 
• 1012057-47-4 7-methoxy-6-nitroquinazolin-4(3H)-one 
• 162012-71-7 4,7-dichloro-6-nitro-quinazoline 
• 81946-00-1 3-Butyl-7-chloro-6-nitro-3H-quinazolin-4-one 
• 81946-01-2 7-Chloro-3-heptyl-6-nitro-3H-quinazolin-4-one 
• 395066-45-2 7-[(1R,2S,3R,4S)-2,3-O-isopropylidene-2,3,4-trihydroxycyclopent-1-yl]amino-6-nitro-4-quinazolone 
• 168761-38-4 7-chloro-4-(benzylamino)-6-nitroquinazoline 
• 1026197-27-2 (7-chloro-6-nitro-quinazolin-4-yl)-(4-methyl-benzyl)-amine 
• 1028270-66-7 (7-chloro-6-nitro-quinazolin-4-yl)-(2-methoxy-benzyl)-amine 

Relevant academic research and scientific papers

Synthesis of alkylamino quinazolines and anti-tumor activity thereof

The present invention provides a compound represented by formula (I), or a pharmaceutically acceptable salt, or ester, or prodrug thereof. The invention further provides a compound represented by the formula (I) or a pharmaceutically acceptable salt or ester, or a synthetic method of the prodrug and an application of the compound in preparation of a medicament for treating tumors.

Synthesis and pharmacological evaluation of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as sigma-2 receptor ligands

Increasing evidences have implicated that sigma-2 receptor is a biomarker and significantly over-expressed in many proliferative cancer cells with no or low expression in normal cells. Sigma-2 receptor selective ligands have been successfully used as valuable tools to study its pharmacological functions, tumor imaging, and cancer therapeutics or adjuvants. 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinolinylalkyl benzamides are among a few categories of structures that have demonstrated high affinities and selectivities for sigma-2 receptor and been used extensively as study tools in various tumor imaging and therapy. As a continuous effort, we have synthesized a new series of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives and evaluated their affinities for both sigma-1 and sigma-2 receptors. Most of these newly developed analogs showed good to excellent binding affinities for sigma-2 receptor with no or low affinities for sigma-1 receptor. In particular, compounds 3b, 3e, 4b, and 4e demonstrated Ki values of 5–6 nM affinities and excellent selectivities for sigma-2 receptor. In addition, these analogs also demonstrated moderate anticancer activities against human liver Huh-7 tumor cells and human esophagus KYSE-140 cancer cells. But their cytotoxicities seem not to be correlated with their sigma-2 receptor affinities.

Tetrahydroisoquinoline derivatives preparation and application of (by machine translation)

The invention mainly relates to a series of containing tetrahydroisoquinoline structure the synthesis of the compounds and in the medical field of application. Specifically, the invention relates to a series of tetrahydroisoquinoline structure compound, it can inhibit the polymerization of A β, antagonizing A β O in combination and in nerve cells caused by the cytotoxic, therapeutic or improve AD has application prospect. (by machine translation)

Phenyl [...] compound and its preparation method, pharmaceutical composition, drug use (by machine translation)

The invention provides a phenylurea coupling quinazoline compound or a pharmaceutically acceptable salt thereof represented by formula (I), wherein R1 represents H, represents Br, Cl or F, represents -CH3, -CH2-CH3, -CH2(CH3)2 or -CF3, represents -O-CH3, -O-CH2-CH3 or -O-CH2(CH3)2, or represents -C[triple bond]CH or -C[triple bond]N; n1 is 1, 2, 3, 4 or 5; one of R2 and R3 is a group represented by formula (II); R4 represents H, represents Br, Cl or F, represents -CH3, -CH2-CH3, -CH2(CH3)2 or -CF3, represents -O-CH3, -O-CH2-CH3 or -O-CH2(CH3)2, represents -NH2, or represents -NO2; n2 is 1, 2, 3, 4 or 5; and the other one of R2 and R3 represents H, -O-CH3, -O-CH2-CH3, -O-CH2(CH3)2, or the following groups.

Artemisin derivative and its preparation and use

Provided are artemisinin derivatives of formula (I) or pharmaceutically acceptable salts thereof, or enantiomers, diastereomers, and racemic bodies thereof, and a pharmaceutical composition of the compounds, the preparation process and uses thereof. Artemisinin derivatives of formula (I) have excellent effects in the treatment of tumours.

Synthesis, biological evaluation and QSAR study of a series of substituted quinazolines as antimicrobial agents

A novel series of 1-N-substituted-3-(4-(5-(pyridin-3-yl)-1,3,4-oxadiazol-2- ylthio)quinazolin-6-yl)urea/thiourea derivatives (6a-6r) and 1-N-substituted-3-(7-(4-methylpiperazin-1-yl)-4-(5-(pyridin-3-yl)-1,3, 4-oxadiazol-2-ylthio)quinazolin-6-yl)urea/thiourea derivatives (14a-14s) were synthesized and screened for antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli. Biological results indicated that the synthesized compounds showed a broad-spectrum activity against tested microorganisms at MIC values between 6.25 and 100 μg/mL. Compound 6r showed a broad spectrum of activity and was found to be active against all tested species. A quantitative structure-activity relationship study has been carried out on the synthesized compounds to get better insights into pharmacophoric features responsible for the antibacterial activity. Genetic function approximation technique was used to identify descriptors that influence biological activity. Hydrophobic (AlogP98), electronic (atomic polarizability), and topological (radius of gyration) descriptors were found to affect the activity significantly. Generated model was found to be statistically significant (r 2 = 0.86, predictive index = 0.96) and predictive as indicated by very low residuals in internal and external cross-validation.

Design, synthesis and biological evaluation of novel 4-anilinoquinazolines with C-6 urea-linked side chains as inhibitors of the epidermal growth factor receptor

A novel series of anilinoquinazoline compounds with C-6 urea-linked side chains was designed and synthesized as reversible inhibitors of epidermal growth factor receptor (EGFR) based on the structure-activity relationships (SARs) of anilinoquinazoline inhibitors. All compounds demonstrated good inhibition of EGFR wild type (EGFR wt) (IC50 = 0.024-1.715 μM) and inhibited proliferation of A431cell line (IC50 = 0.116-22.008 μM). The binding mode of compounds 8a, 8d, 8k and 8o was consistent with the biological results. Moreover, compounds 8k and 8l almost completely blocked the phosphorylation of EGFR in A431 cell line at 0.01 μM. Interestingly, all of the compounds also demonstrated moderate inhibition of EGFR/T790M/L858R (IC 50 = 0.049-5.578 μM). In addition, compounds 8f and 8h blocked the autophosphorylation of EGFR in NCI-H1975 cells at high concentration (10 μM), and compound 8f was confirmed to be an irreversible inhibitor through the dilution method. Importantly, the compounds with C-6 urea-linked side chains which did not contain Michael acceptors demonstrated moderate to strong irreversible EGFR inhibition.

Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides

Irreversible epidermal growth factor receptor (EGFR) inhibitors contain a reactive warhead which covalently interacts with a conserved cysteine residue in the kinase domain. The acrylamide fragment, a commonly employed warhead, effectively alkylates Cys797 of EGFR, but its reactivity can cause rapid metabolic deactivation or nonspecific reactions with off-targets. We describe here a new series of irreversible inhibitors containing a 3-aminopropanamide linked in position 6 to 4-anilinoquinazoline or 4-anilinoquinoline-3- carbonitrile driving portions. Some of these compounds proved to be as efficient as their acrylamide analogues in inhibiting EGFR-TK (TK = tyrosine kinase) autophosphorylation in A549 lung cancer cells. Moreover, several 3-aminopropanamides suppressed proliferation of gefitinib-resistant H1975 cells, harboring the T790M mutation in EGFR, at significantly lower concentrations than did gefitinib. A prototypical compound, N-(4-(3-bromoanilino)quinazolin-6- yl)-3-(dimethylamino)propanamide (5), did not show covalent binding to cell-free EGFR-TK in a fluorescence assay, while it underwent selective activation in the intracellular environment, releasing an acrylamide derivative which can react with thiol groups.

TARTRATE SALTS OF QUINAZOLINE BASED EGFR INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to tartrate salts of quinazoline containing zinc-binding moiety based derivatives that are inhibitors of epidermal growth factor receptor tyrosine kinase (EGFR-TK) and their use in the treatment of EGFR-TK related diseases and disorders such as cancer. The tartrate salts may further act as HDAC inhibitors.

FORMULATION OF QUINAZOLINE BASED EGFR INHIBITORS CONTAINING A ZINC BINDING MOIETY

The present invention relates to a composition comprising an inclusion complex of a cyclodextrin and quinazoline containing zinc-binding moiety based derivatives. The cyclodextrin is preferable a β-cyclodextrin or a derivative thereof. The quinazolines have enhanced and unexpected properties as inhibitors of epidermal growth factor receptor tyrosine kinase (EGFR-TK) and their use in the treatment of EGFR-TK related diseases and disorders such as cancer. The said derivatives may further act as HDAC inhibitors.