3817-05-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(Chloromethyl)-4(3H)-quinazolinone is used as a therapeutic agent for its potential anti-inflammatory and anti-cancer properties, targeting conditions such as asthma, arthritis, and specific types of cancer. Its mechanism of action involves antagonism of the human A3 adenosine receptor, which plays a crucial role in inflammation and immune response regulation.
Used in Research Applications:
In the field of scientific research, 2-(Chloromethyl)-4(3H)-quinazolinone is utilized as a tool compound to study the role of the A3 adenosine receptor in various physiological and pathological processes. This helps in understanding the receptor's influence on inflammation, immune responses, and other related biological functions.
Used in Drug Development:
CMQ is also employed in the development of new drugs, as its interaction with the A3 adenosine receptor can provide insights into the creation of novel therapeutics that may have applications in treating inflammatory and immune-related disorders, as well as certain cancers.

InChI:InChI=1/C9H7ClN2O/c10-5-8-11-7-4-2-1-3-6(7)9(13)12-8/h1-4H,5H2,(H,11,12,13)

Upstream product

• 21721-78-8 2-ω-chloroacetylaminobenzamide 
• 118-92-3 anthranilic acid 
• 107-14-2 chloroacetonitrile 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 28144-70-9 anthranilic acid amide 
• 134-20-3 2-carbomethoxyaniline 
• 32807-28-6 Methyl 4-chloroacetoacetate 
• 79-04-9 chloroacetyl chloride 
• 1885-29-6 anthranilic acid nitrile 
• 87-25-2 2-ethoxycarbonylaniline 
• 79-11-8 chloroacetic acid 
• 71993-21-0 [(2-cyanophenyl)aminocarbonylmethyl]chloride 
• 1769-24-0 2-methyl-4-quinazolone 
• 58915-18-7 methyl N-(chloroacetyl)anthranilate 

Downstream Products

• 134577-54-1 2-[(4-Chloro-phenylamino)-methyl]-3H-quinazolin-4-one 
• 3817-06-9 2-Phenylaminomethyl-3H-quinazolin-4-one 
• 134577-53-0 2-[(4-Ethoxy-phenylamino)-methyl]-3H-quinazolin-4-one 
• 134577-51-8 2-[(4-Ethyl-phenylamino)-methyl]-3H-quinazolin-4-one 
• 34637-41-7 4-chloro-2-(chloromethyl)quinazoline 
• 125983-52-0 4-Oxo-3,4-dihydro-quinazoline-2-carbothioic acid (4-diethylamino-phenyl)-amide 
• 125983-51-9 N-{4-[(4-Oxo-3,4-dihydro-quinazoline-2-carbothioyl)-amino]-phenyl}-acetamide 
• 134577-61-0 2-Phenyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 
• 134577-62-1 2-p-Tolyl-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 
• 134577-63-2 2-(4-Ethyl-phenyl)-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 
• 134577-66-5 2-(4-Chloro-phenyl)-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 
• 134577-64-3 2-(4-Methoxy-phenyl)-1,2-dihydro-2,4a,9-triaza-anthracene-3,10-dione 

Relevant academic research and scientific papers

In Vivo and Mechanistic Studies on Antitumor Lead 7-Methoxy-4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one and Its Modification as a Novel Class of Tubulin-Binding Tumor-Vascular Disrupting Agents

7-Methoxy-4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one (2), a promising anticancer lead previously identified by us, inhibited tumor growth by 62% in mice at 1.0 mg/kg without obvious signs of toxicity. Moreover, compound 2 exhibited extremely high antiproliferative activity in the NIH-NCI 60 human tumor cell line panel, with low to sub-nanomolar GI50 values (10-10 M level). It also showed a suitable balance between aqueous solubility and lipophilicity, as well as moderate metabolic stability in vivo. Mechanistic studies using Mayer's hematoxylin and eosin and immunohistochemistry protocols on xenograft tumor tissues showed that 2 inhibited tumor cell proliferation, induced apoptosis, and disrupted tumor vasculature. Moreover, evaluation of new synthetic analogues (6a-6t) of 2 indicated that appropriate 2-substitution on the quinazoline ring could enhance antitumor activity and improve druglike properties. Compound 2 and its analogues with a 4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one scaffold thus represent a novel class of tubulin-binding tumor-vascular disrupting agents (tumor-VDAs) that target established blood vessels in tumors.

Design and synthesis of new benzopyrimidinone derivatives: α-amylase inhibitory activity, molecular docking and DFT studies

New benzopyrimidinone derivatives have been synthesized by reaction of 2-aminobenzamide with different acyl chlorides in good yield and their structures were confirmed by 1H NMR, 13C NMR and mass spectrometry. The newly synthesized c

Quinazolin-4(3H)-one based agents bearing thiadiazole-urea: Synthesis and evaluation of anti-proliferative and antiangiogenic activity

A series of quinazolin-4(3H)-one based agents containing thiadiazole-urea were designed, synthesized, and biologically evaluated. The proliferation rate of PC3 cells was moderately reduced by compound 9f (IC50 = 17.7 μM)which was comparable with sorafenib (IC50 = 17.3 μM). There was also a significant reduction in the number of HUVEC cells, when they were exposed to compound 9y (IC50 = 6.1 μM). To test the potential of compounds in inducing apoptosis, Annexin V-FITC/propidium iodide double staining assay was used. After the treatment of HUVEC cells with 9f, they underwent apoptotic effects. A substantial effort was dedicated to gathering comprehensive data across CAM assay. These data showed that 9f moderately inhibits the growth of corresponding blood vessels. Finally, the outcomes of Western blotting proposed a mechanism of action, by which the phosphorylation of VEGFR-2 is inhibited by compounds 9f and 9y.

Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones

A series of novel spiro-substituted 2,3-dihydroquinazolin-4(1H)-ones was synthesized and structurally confirmed by spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. Graphical abstract: [Figure not available: see fulltext.].

Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions

The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.

Tankyrase inhibitor

The invention belongs to the technical field of medicines and particularly relates to a tankyrase inhibitor represented by a general formula (I) shown in the description and pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof, wherein R1, R2, R3, m, n, Z, L, Q, A, X1, X2 and Y are as defined in the description. The invention further relates to a preparation method for the compounds, pharmaceutical preparations and pharmaceutical compositions containing the compounds and application of the compound and the pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof in preparation of drugs for treating and/or preventing tankyrase mediated cancers and related diseases.

A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines

We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.

HETEROCYCLIC COMPOUNDS AS ANTIBIOTIC POTENTIATORS

The invention relates to heterocyclic compounds and their use as antibiotics and/or as antibiotic potentiators. The compounds may act as colistin potentiators and SOS inhibitors.

Synthesis of Benzoxazolylthiomethyl and Benzthiazolylthiomethyl Quinazolin-4(3 h)-ones

o-Aminophenol (1a, X = O) or o-aminothiophenol (1b, X = S) was reacted with carbon disulfide in ethanol containing KOH under reflux to obtain 2-mercaptobenzoxazole (2a, X = O) and 2-mercaptobenzthiazole (2b, X = S), respectively. Condensation of 2a and 2b each with chloroacetic acid gave 2-(benzoxazol-2-ylthio)acetic acid (3a, X = O) and 2-(benzthiazol-2-ylthio)acetic acid (3b, X = S) respectively which with anthranilamide gave 2-((benzoxal-2-ylthio)methyl) quinazolin-4(3H)-one (5a, X = O) and 2-((benzthiazol-2-ylthio)methyl)quinazolin-4(3H)-one (5b, X = S) respectively. The products 5a,b could be prepared in three other routes involving the general sequences 6→2→5, 6→7→5 and 8→9→5.

Synthesis of benzoxazolthiolyl and benzthiazolthiolyl fused 3- alkylquinazolin-4(3H)-ones

Condensation of anthranilamide (1) with chloroacetyl chloride for 1 hr at RT gave 2- (2-chloroacetamido) benzamide (2). The latter, on refluxation in acetic acid for 2 hr gave 2-(chloromethyl) quinazolin-4(3H)-one (3). Condensation of 3, independently, with each one of benz [d] oxazole-2-thiol (4a) and benz [d] thiazole-2-thiol (4b), for 3-4 hr, gave 2-((benz [d] oxazol-2-ylthio) methyl) quinazolin-4(3H)-one (5a) and 2-((benz [d] thiazol-2-ylthio) methyl) quinazolin-4(3H)-one (5b) respectively. Each one of the 5a and 5b, independently and selectively, when treated with alkylating agents (i.e. DMS, DES, PhCH2Cl), gave 2-((benz [d] oxazol-2-ylthio) methyl)-3-alkylquinazolin-4(3H)-ones (6a-c) and 2-((benz [d] thiazol-2-ylthio) methyl)-3-alkylquinazolin-4(3H)-ones (6d-f) respectively. The latter 6a-f could also be prepared, alternatively, by condensing chloromethyl-3-alkylquinazolin-4(3H)-one (7a-c) with 4a-b respectively, in good yields.