59490-94-7

Basic information

• Product Name: 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE
• Synonyms: 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE;Quinazoline, 4-chloro-2-(4-chlorophenyl)-
• CAS NO: 59490-94-7
• Molecular Formula: C₁₄H₈Cl₂N₂
• Molecular Weight: 275.13
• Mol File: 59490-94-7.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE(59490-94-7)
• EPA Substance Registry System: 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE(59490-94-7)

Safety Data

• Hazardous Substances Data: 59490-94-7(Hazardous Substances Data)

Usage

General Description

4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE, also known as 4-chloro-2-(4-chlorophenyl)quinazoline, is a chemical compound with the molecular formula C15H9Cl2N3. It is a quinazoline derivative that contains two chlorine atoms and a phenyl group. 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE is used in the synthesis of pharmaceuticals and agrochemicals, and it has potential antitumor activity. It may also have applications in the field of organic chemistry as a building block for the development of new chemical compounds. The characteristics and properties of 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE make it an important intermediate for the development of various products in the chemical and pharmaceutical industries.

Upstream product

• 7455-77-8 2-(4-chlorophenyl)-4(3H)-quinazolinone 
• 18600-52-7 2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 
• 118-92-3 anthranilic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 104-88-1 4-chlorobenzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 52962-92-2 2-(4-Chlorobenzamido)benzamide 

Downstream Products

• 144924-51-6 4-(4-Chloro-phenyl)-1,2,3,3a,5-pentaaza-cyclopenta[a]naphthalene 
• 144924-43-6 10-Chloro-6-(4-chloro-phenyl)-quinazolino[4,3-b]quinazolin-8-one 
• 73565-12-5 6-(4-chloro-phenyl)-quinazolino[4,3-b]quinazolin-8-one 
• 1257346-17-0 C₂₄H₂₁ClN₄ 
• 1257346-08-9 C₂₅H₂₂ClN₃ 
• 316125-24-3 2-(4-chlorophenyl)-4-(4-methylpiperidin-1-yl)quinazoline 
• 316125-27-6 2-(4-chlorophenyl)-4-(4-methylpiperazin-1-yl)quinazoline 

Relevant articles and documents

Synthesis, in vitro cytotoxic, anti-Mycobacterium tuberculosis and molecular docking studies of 4-pyridylamino- and 4-(ethynylpyridine)quinazolines

A series of 4-(pyridylamino)- and 4-(ethynylpyridine)quinazolines were successfully prepared via Sonogashira cross-coupling and dechloroamination reactions on the C(4)-Cl position of the requisite 2-(p-phenyl)-4-chloroquinazolines. The prepared compounds were characterized by means of 1H- and 13C-NMR, FT-IR and mass spectrometry techniques. The structure of 2-(4-chlorophenyl)-4-(2-(pyridin-4-yl) ethynyl) quinazoline from the 4-(ethynylpyridine) series was confirmed by single crystal X-ray analysis which indicates monoclinic crystal system and P21/c space group. Compounds from the 4-chloro-, 4-(pyridylamino)- and 4-(ethynylpyridine)-quinazoline series were evaluated for anti-Mycobacterium tuberculosis (Mtb) properties in vitro employing rifampicin as a reference drug. The results from the Alamar Blue assay (Mtb H37Rv strain) revealed promising MIC90 ranging from 125 μM. The cytotoxicity of the synthesised compounds was tested against the Raw 264.7 microphage cell line at a maximum concentration of 50 μM. The possible mode of interaction against the Mtb was theoretically explained through molecular 3ZXR protein and the more prominent hydrogen bond is observed between the nitrogen of the pyridine ring moiety of the 5 and 6 series with OH group of SER280. Also, a metal coordination between the methoxy benzene moiety of compound 6e and Mg2+ is also observed, explaining the SAR of these compounds to MtGS.

Domino synthesis of pyrimido and imidazoquinazolinones

A simple method for the synthesis of N-alkyl-2-arylquinazolin-4-amines, methyl 4-((2-arylquinazolin-4-yl)amino) butanoates, 6-aryl-2,3-dihydro-4H-pyrimido[1,2-c]quinazolin-4-ones, and 5-arylimidazo[1,2-c]quinazolin-3(2H)-ones has been described. It involves a simple reaction of N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides with alkylamine, γ-aminobutyric acid, β-alanine, l-alanine, and glycine methyl esters hydrochloride in acetonitrile to afford the desired compounds after a series of instantaneous reactions that include Dimroth rearrangement. The reaction involves reflux for 12 hours, simple addition of reagents to an in situ generated benzimidoyl chloride, and simple workup, to form 21 examples of pure compounds in high yields. The active intermediate N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides were formed by the reaction of N-(2-cyanophenyl)-substitutedbenzamides with thionyl chloride in a one-pot strategy. The alternative method described for this preparation deals with an exhausting multistep reactions starting from anthranilic acid.

Design, Synthesis, and Pharmacological Characterization of N-(4-(2 (6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)yl)ethyl)phenyl)quinazolin-4-amine Derivatives: Novel Inhibitors Reversing P-Glycoprotein-Mediated Multidrug Resistance

P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a principal obstacle for successful cancer chemotherapy. A novel P-gp inhibitor with a quinazoline scaffold, 12k, was considered to be the most promising for in-depth study. 12k possessed high potency (EC50 = 57.9 ± 3.5 nM), low cytotoxicity, and long duration of activity in reversing doxorubicin (DOX) resistance in K562/A02 cells. 12k also boosted the potency of other MDR-related cytotoxic agents with different structures, increased accumulation of DOX, blocked P-gp-mediated Rh123 efflux, and suppressed P-gp ATPase activity in K562/A02 MDR cells. However, 12k did not have any effects on CYP3A4 activity or P-gp expression. In particular, 12k had a good half-life and oral bioavailability and displayed no influence on DOX metabolism to obviate the side effects closely related to increased plasma concentrations of cytotoxic agents in vivo.