59490-94-7

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE is used as an intermediate in the synthesis of pharmaceuticals for its potential antitumor activity. It contributes to the development of new drugs targeting cancer treatment by providing a structural foundation for the creation of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE serves as a key intermediate in the production of agrochemicals. Its incorporation into these products can enhance their effectiveness in pest control and crop protection, thereby supporting agricultural productivity.
Used in Organic Chemistry:
4-CHLORO-2-(4-CHLORO-PHENYL)-QUINAZOLINE is utilized as a building block in organic chemistry for the development of new chemical compounds. Its unique structure allows for the creation of a variety of novel molecules with potential applications in various industries, showcasing its versatility as a synthetic precursor.

Upstream product

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

Downstream Products

• 73565-12-5 6-(4-chloro-phenyl)-quinazolino[4,3-b]quinazolin-8-one 
• 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 
• 144924-46-9 10,12-Dichloro-6-(4-chloro-phenyl)-quinazolino[4,3-b]quinazolin-8-one 
• 316125-27-6 2-(4-chlorophenyl)-4-(4-methylpiperazin-1-yl)quinazoline 
• 316125-24-3 2-(4-chlorophenyl)-4-(4-methylpiperidin-1-yl)quinazoline 
• 1257346-08-9 C₂₅H₂₂ClN₃ 
• 1257346-17-0 C₂₄H₂₁ClN₄ 

Relevant academic research and scientific papers

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.

Synthesis and evaluation of new quinazoline-benzimidazole hybrids as potent anti-microbial agents against multidrug resistant Staphylococcus aureus and Mycobacterium tuberculosis

Owing to the rapid rise in antibiotic resistance, infectious diseases have become serious threat to public health. There is an urgent need to develop new antimicrobial agents with diverse chemical structures and novel mechanisms of action to overcome the resistance. In recent years, Quinazoline-benzimidazole hybrids have emerged as a new class of antimicrobial agents active against S. aureus and M. tuberculosis. In the current study, we designed and synthesized fifteen new Quinazoline-benzimidazole hybrids and evaluated them for their antimicrobial activity against S. aureus ATCC 29213 and M. tuberculosis H37Rv. These studies led to the identification of nine potent antibacterial agents 8a, 8b, 8c, 8d, 8f, 8g, 8h, 8i and 10c with MICs in the range of 4–64 μg/mL. Further, these selected compounds were found to possess potent antibacterial potential against a panel of drug-resistant clinical isolates which include methicillin and vancomycin-resistant S. aureus. The selected compounds were found to be less toxic to Vero cells (CC50 = 40-≥200 μg/mL) and demonstrated a favourable selectivity index. Based on the encouraging results obtained these new benzimidazol-2-yl quinazoline derivatives have emerged as promising antimicrobial agents for the treatment of MDR- S. aureus and Mycobacterial infections.

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.

Synthesis, Crystal Structure, and Agricultural Antimicrobial Evaluation of Novel Quinazoline Thioether Derivatives Incorporating the 1,2,4-Triazolo[4,3- a]pyridine Moiety

A total of 22 quinazoline thioether derivatives incorporating a 1,2,4-triazolo[4,3-a]pyridine moiety were designed, synthesized, and evaluated as antimicrobial agents in agriculture. Among these compounds, the chemical structure of compound 6l was further confirmed via single-crystal X-ray diffraction analysis. The bioassay results revealed that some of the compounds possessed noticeable in vitro antibacterial activities against the tested phytopathogenic bacteria. For example, compounds 6b and 6g had EC50 values as low as 10.0 and 24.7 μg/mL against Xanthomonas axonopodis pv. citri (Xac), respectively, which were significantly better than that of the commercial agrobactericide bismerthiazol (56.9 μg/mL). Particularly, compound 6b was also found to be capable of suppressing the pathogenic bacterium Xanthomonas oryzae pv. oryzae (Xoo) approximately 12-fold more potent than control bismerthiazol, in terms of their EC50 values (7.2 versus 89.8 μg/mL). Importantly, the most active compound 6b turned out to be one with the highest hydrophilicity and the lowest molecular weight within the series. In vivo bioassays further showed the application prospect of 6b as a promising plant bactericide for controlling Xoo. Additionally, in vitro antifungal activities of these compounds were also evaluated at the concentration of 50 μg/mL. Overall, the present study demonstrated the potential of 1,2,4-triazolo[4,3-a]pyridine-bearing quinazoline thioether derivatives as efficient agricultural antibacterial agents for crop protection.

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.

Synthesis and in vitro anti-proliferative activity of some novel isatins conjugated with quinazoline/phthalazine hydrazines against triple-negative breast cancer MDA-MB-231 cells as apoptosis-inducing agents

Treatment of patients with triple-negative breast cancer (TNBC) is challenging due to the absence of well- defined molecular targets and the heterogeneity of such disease. In our endeavor to develop potent isatin-based anti-proliferative agents, we utiliz

Development of certain new 2-substituted-quinazolin-4-ylaminobenzenesulfonamide as potential antitumor agents

Carbonic anhydrases (CA I, II, IX and XII) are known to be highly expressed in various human malignancies. CA IX is overexpressed in colorectal cancer specifically in hereditary nonpolyposis colorectal cancer. Inhibition of CA activity by small molecular CA inhibitor like sulphonamides, sulphonamide derivative (SU.D2) or HIF1a inhibitor Chetomin leads to inhibition of tumorigenesis. Eighteen new quinazolin-4-sulfonamide derivatives were prepared and characterized by means of IR, NMR and mass spectra. Certain selected derivatives were tested for their ability to inhibit four isoforms of the metalloemzyme CA, namely, CA I, CA II, CA IX and CA XII. Compound 3c was found to be highly effective in inhibiting the cancer cell proliferation. 3c decreased cell viability of human HT-29 cells in dose and time dependent manner and with IC50 of 5.45 mM. Moreover, it was tested on metastatic colon cancer cell SW-620 where it was found to be equally effective on human SW-620 cells. This novel compound inhibited the CA IX and CA XII protein expression in HT-29 cells without affecting CA I and CA II expression. These findings indicate that 3c inhibits cellular proliferation in two human colon cancer cells by specifically targeting the CA IX and CA XII expression.

Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives

Two series of some new 2,4,6-trisubstituted-quinazoline derivatives were prepared and screened for their analgesic, anti-inflammatory activity and acute toxicity. Four compounds were more potent analgesic agents than the reference drug Indomethacin and thirteen compounds showed significant anti-inflammatory activity. Seven compounds showed combined ability to inhibit both pain and inflammation. Compounds tested for acute toxicity showed no toxic symptoms or mortality rates 24 h post-administration implying their good safety margin.

Quinazoline derivatives as medicaments

The invention is directed to methods to inhibit TGF-β and/or p38-α kinase using compounds of the formula or the pharmaceutically acceptable salts thereof wherein R3is a noninterfering substituent; each Z is CR2or N, wherein no more t