20028-68-6

Usage

Uses

Used in Pharmaceutical Industry:
2,4,6-Trichloroquinazoline is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure contributes to the development of new drugs, enhancing the therapeutic potential of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 2,4,6-trichlorquinazoline is utilized as an intermediate in the production of agrochemicals. It aids in the creation of effective pesticides and other agricultural chemicals that protect crops and enhance yield.
Used in Materials Science:
2,4,6-Trichloroquinazoline is used as a building block in materials science. Its properties allow it to be incorporated into the development of new materials with specific characteristics for various applications.
Used in Research and Development:
2,4,6-TRICHLOROQUINAZOLINE is used in research and development for new chemical processes and products. Its versatility and reactivity make it a valuable component in exploring and creating innovative chemical entities and processes.

InChI:InChI=1/C8H3Cl3N2/c9-4-1-2-6-5(3-4)7(10)13-8(11)12-6/h1-3H

Upstream product

• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 503-38-8 trichloromethyl chloroformate 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 134-20-3 2-carbomethoxyaniline 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 57-13-6 urea 
• 635-21-2 5-chloroanthranilic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1095657-56-9 6-chloroquinazoline-2,4(1H,3H)-dione monopotassium salt 
• 1640-60-4 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione 
• 1640-60-4 2,4-dihydroxy-6-chloroquinazoline 
• 784183-51-3 N-(4-chloro-2-iodophenyl)-2,2,2-trifluoroacetamide 
• 63069-48-7 p-chloro-o-iodoaniline 
• 618889-14-8 N-(4-Chloro-2-cyanophenyl)-2,2,2-trifluoroacetamide 

Downstream Products

• 1640-60-4 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione 
• 76004-42-7 N-(2,6-Dichloro-quinazolin-4-yl)-N',N'-diethyl-cyclohexane-1,4-diamine; hydrochloride 
• 150450-96-7 N-benzyl-2,6-dichloroquinazolin-4-amine 
• 20197-87-9 2,6-dichloro-3H-quinazolin-4-one 
• 76004-86-9 NCI 151998 
• 76004-87-0 6-Chloro-N²-(3,5-dichloro-phenyl)-N⁴-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-quinazoline-2,4-diamine; hydrochloride 
• 76004-90-5 NCI 152189 
• 76004-88-1 6-Chloro-N²-(3,4-dichloro-phenyl)-N⁴-(1-ethyl-piperidin-3-yl)-quinazoline-2,4-diamine; hydrochloride 
• 76004-94-9 6-Chloro-N²-(3,4-dichloro-phenyl)-N⁴-(4-diethylamino-cyclohexyl)-quinazoline-2,4-diamine; hydrochloride 
• 76005-03-3 7-Chloro-N⁴-(2-diethylamino-ethyl)-N²-(3-diethylaminomethyl-4-ethoxy-phenyl)-quinazoline-2,4-diamine; hydrochloride 
• 76005-02-2 6-Chloro-N⁴-(2-diethylamino-ethyl)-N²-(3-diethylaminomethyl-4-ethoxy-phenyl)-quinazoline-2,4-diamine; hydrochloride 
• 76005-04-4 6-Chloro-N⁴-(2-diethylamino-ethyl)-N²-(4-ethoxy-3-pyrrolidin-1-ylmethyl-phenyl)-quinazoline-2,4-diamine; hydrochloride 
• 76005-05-5 7-Chloro-N⁴-(2-diethylamino-ethyl)-N²-(4-ethoxy-3-pyrrolidin-1-ylmethyl-phenyl)-quinazoline-2,4-diamine; hydrochloride 
• 147971-96-8 4'-[[(2,6-dichloro-4-quinazolinyl)amino]methyl][1,1'-biphenyl]-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

One-pot cascade ring enlargement of isatin-3-oximes to 2,4-dichloroquinazolines mediated by bis(trichloromethyl)carbonate and triarylphosphine oxide

An efficient and convenient one-pot cascade synthesis of 2,4-dichloroquinazolines directly from isatin-3-oximes with the addition of bis(trichloromethyl)carbonate and triarylphosphine oxide was developed, leading to substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a range of functional groups. Thus, the method represents a convenient and practical strategy for the synthesis of substituted 2,4-dichloroquinazolines.

Design, synthesis, and anticancer activities of sodium quinazolin-4-diselenide compounds

Substituted 4-chloroquinazoline reacted with sodium diselenide to give novel sodium quinazoline-4-diselenide compounds. The reaction provides an efficient and facile approach to the synthesis of sodium quinazoline-4-diselenide compounds. Structures of title compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. MTT assay was adopted to show anticancer activities of the compounds. Compounds 5a and 5h showed good activities against cancer-cell lines MDA-MB-435, MDA-MB-231, A549, SiHa, and HeLa. In addition, 5a exhibited quite good anticancer effects on relative above cell lines with 10μM concentration compared with oxaliplatin and gefitinib of the commercial anticancer drugs.

Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles

Molecular hybridization is a powerful strategy in drug discovery. A series of novel diarylbenzopyrimidine (DABP) analogues were developed by the hybridization of FDA-approved drugs etravirine (ETR) and efavirenz (EFV) as potential HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs). Substituent modifications resulted in the identification of new DABPs with the combination of the strengths of the two drugs, especially compound 12d, which showed promising activity toward the EFV-resistant K103N mutant. 12d also had a favorable pharmacokinetic (PK) profile with liver microsome clearances of 14.4 μL/min/mg (human) and 33.2 μL/min/mg (rat) and an oral bioavailability of 15.5% in rat. However, its activity against the E138K mutant was still unsatisfactory; E138K is the most prevalent NNRTI resistance-associated mutant in ETR treatment. Further optimizations resulted in a highly potent compound (12z) with no substituents on the phenyl ring and a 2-methyl-6-nitro substitution pattern on the 4-cyanovinyl-2,6-disubstitued phenyl motif. The antiviral activity of this compound was much higher than those of ETR and EFV against the WT, E138K, and K103N variants (EC50 = 3.4, 4.3, and 3.6 nM, respectively), and the cytotoxicity was decreased while the selectivity index (SI) was increased. In particular, this compound exhibited acceptable intrinsic liver microsome stability (human, 34.5 μL/min/mg; rat, 33.2 μL/min/mg) and maintained the good PK profile of its parent compound EFV and showed an oral bioavailability of 16.5% in rat. Molecular docking and structure-activity relationship (SAR) analysis provided further insights into the binding of the DABPs with HIV-1 reverse transcriptase and provided a deeper understanding of the key structural features responsible for their interactions.

PIPERAZINE DERIVATIVES AS MAGL INHIBITORS

The invention provides new heterocyclic compounds having general Formula (I), or a pharmaceutically acceptable salt thereof, wherein R1, R2, X, Y1 and Y2 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

Discovery of 2-(4-Substituted-piperidin/piperazine-1-yl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-quinazoline-2,4-diamines as PAK4 inhibitors with potent A549 cell proliferation, migration, and invasion inhibition activity

A series of novel 2,4-diaminoquinazoline derivatives were designed, synthesized, and evaluated as p21-activated kinase 4 (PAK4) inhibitors. All compounds showed significant inhibitory activity against PAK4 (half-maximal inhibitory concentration IC50 1 ?M). Among them, compounds 8d and 9c demonstrated the most potent inhibitory activity against PAK4 (IC50 = 0.060 ?M and 0.068 ?M, respectively). Furthermore, we observed that compounds 8d and 9c displayed potent antiproliferative activity against the A549 cell line and inhibited cell cycle distribution, migration, and invasion of this cell line. In addition, molecular docking analysis was performed to predict the possible binding mode of compound 8d. This series of compounds has the potential for further development as PAK4 inhibitors for anticancer activity.

Pyrimidine derivatives, preparation method therefor and application of pyrimidine derivatives

The invention belongs to the field of drug synthesis and relates to novel pyrimidine derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, preparation methods of thenovel pyrimidine derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof and use of the novel pyrimidine derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of therapeutic agents, particularly PAK inhibitors. The derivatives disclosed by the invention are represented by a general formula (I) or (II), wherein each substituent is as defined in claims.

Structure-Based Design of 6-Chloro-4-aminoquinazoline-2-carboxamide Derivatives as Potent and Selective p21-Activated Kinase 4 (PAK4) Inhibitors

Herein, we report the discovery and characterization of a novel class of PAK4 inhibitors with a quinazoline scaffold. Based on the shape and chemical composition of the ATP-binding pocket of PAKs, we chose a 2,4-diaminoquinazoline series of inhibitors as a starting point. Guided by X-ray crystallography and a structure-based drug design (SBDD) approach, a series of novel 4-aminoquinazoline-2-carboxamide PAK4 inhibitors were designed and synthesized. The inhibitors' selectivity, therapeutic potency, and pharmaceutical properties were optimized. One of the best compounds, 31 (CZh226), showed remarkable PAK4 selectivity (346-fold vs PAK1) and favorable kinase selectivity profile. Moreover, this compound potently inhibited the migration and invasion of A549 tumor cells by regulating the PAK4-directed downstream signaling pathways in vitro. Taken together, these data support the further development of 31 as a lead compound for PAK4-targeted anticancer drug discovery and as a valuable research probe for the further biological investigation of group II PAKs.

Application of quinazoline and pyrido[3,2-: D] pyrimidine templates to design multi-targeting agents in Alzheimer's disease

A quinazoline and pyrido[3,2-d]pyrimidine based compound library was designed, synthesized and evaluated as multi-targeting agents aimed at Alzheimer's disease (AD). The SAR studies identified compound 8h (8-chloro-N2-isopropyl-N4-ph

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles

The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.

SUBSTITUTED QUINAZOLINE COMPOUNDS AND PREPARATION AND USES THEREOF

The present invention relates quinazolinone compounds of Formula (I), as well as their preparation and uses, and further relates pharmaceutical compositions comprising these compounds and their uses； wherein the compounds or pharmaceutical compositions disclosed herein can be used for antagonizing the orexin receptor. The present invention also relates to uses of the compounds or pharmaceutical compositions in treating or preventing neurological and psychiatric disorders and diseases of the central nervous system in mammals, especially in humans.