873208-55-0

Basic information

• Product Name: 2-(CHLOROMETHYL)-3-(4-FLUOROPHENYL)QUINAZOLIN-4(3H)-ONE
• Synonyms: 2-(CHLOROMETHYL)-3-(4-FLUOROPHENYL)QUINAZOLIN-4(3H)-ONE
• CAS NO: 873208-55-0
• Molecular Formula: C₁₅H₁₀ClFN₂O
• Molecular Weight: 288.7
• Mol File: 873208-55-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(CHLOROMETHYL)-3-(4-FLUOROPHENYL)QUINAZOLIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-3-(4-FLUOROPHENYL)QUINAZOLIN-4(3H)-ONE(873208-55-0)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-3-(4-FLUOROPHENYL)QUINAZOLIN-4(3H)-ONE(873208-55-0)

Safety Data

• Hazardous Substances Data: 873208-55-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(chloromethyl)-3-(4-fluorophenyl)quinazolin-4(3H)-one is used as a potential anti-cancer agent for its ability to target and inhibit the growth of cancer cells. Its specific chemical structure allows it to interact with biological targets, making it a promising candidate for the development of new cancer therapies.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-(chloromethyl)-3-(4-fluorophenyl)quinazolin-4(3H)-one serves as a valuable compound for studying the structure-activity relationships of quinazolinone derivatives. Its unique features, such as the chloromethyl and 4-fluorophenyl groups, provide insights into the design and optimization of novel pharmaceutical agents with improved efficacy and selectivity.
Used in Drug Discovery and Development:
2-(chloromethyl)-3-(4-fluorophenyl)quinazolin-4(3H)-one is utilized in drug discovery and development processes to identify new lead compounds with potential therapeutic applications. Its pharmacological properties and interactions with biological targets can guide the synthesis and modification of related compounds, leading to the development of more effective drugs for various diseases and disorders.

Upstream product

• 371-40-4 4-fluoroaniline 
• 14422-49-2 2-chloroacetamidobenzoic acid 
• 98592-35-9 2-(chloromethyl)-4H-benzo[d][1,3]oxazin-4-one 
• 118-92-3 anthranilic acid 

Downstream Products

• 708293-58-7 3-(4-fluorophenyl)-2-((4-(furan-2-carbonyl)piperazin-1-yl)methyl)quinazolin-4(3H)-one 

Relevant articles and documents

2-(Chloromethyl)-3-phenylquinazolin-4(3H)-ones as potent anticancer agents; cytotoxicity, molecular docking and in silico studies

Abstract: In order to show antiproliferation and cancerous cell growth inhibition of quinazoline derivatives, a series of 2-(chloromethyl)-3-phenylquinazolin-4(3H)-ones (H1–H11) were synthesized. In vitro cytotoxic activities were evaluated against three human cancer cell lines: A549, MCF-7 and SW1116 using colorimetric MTT assay. Comparing their effects together and with cisplatin as a positive control indicated that H3, H5 and H6 exhibited better antitumor activities on A549 cell line with IC50 values less than 10?μM versus 12?μM for cisplatin. In the case of MCF-7 and SW1116 cell lines, almost all compounds displayed better cytotoxic activities than cisplatin. Molecular docking studies were applied on epidermal growth factor receptor (EGFR) as the main target of quinazoline scaffolds in cancer therapy to predict the binding energies, binding modes and orientation of these ligands toward the active site of the receptor. In silico physicochemical parameters and ADMET profiling calculations also were done. All compounds showed lower binding energies than erlotinib, the inhibitor of EGFR. Taken together, our findings showed potential anticancer effect of quinazoline compounds bearing various phenyl ring substitutions. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis, molecular simulation, and biological activities of novel quinazolinone-pyrimidine hybrid derivatives as dipeptidyl peptidase-4 inhibitors and anticancer agents

Two novel series of quinazolinone-pyrimidine (series a: 9a-9i) and benzyl-pyrimidine hybrids (series b: 12a-12c) were designed, synthesized and characterized by spectroscopic methods. The dipeptidyl peptidase-4 inhibition potencies of these compounds were assessed through a MAK 203 kit. Compound 9e was found to be the most potent agent with an IC50 value of 34.3 ± 3.3 μM. A kinetic study revealed that it acted as a competitive inhibitor. Molecular modeling of these compounds was in agreement with the in vitro results. Due to the crucial role of dipeptidyl peptidase-4 in cancer therapy, the cytotoxic activities of the compounds were also evaluated against three cancerous cell lines (HT-29, SW1116 and A549). Almost all the compounds displayed better antiproliferative activity on colon cancer cell lines (HT-29 and SW1116) compared to a lung cancer cell line (A549). Compounds 9e and 12c exhibited significant activity toward the HT-29 cell line with an IC50 of 10.67 ± 0.3 μM and 27.9 ± 6.5 μM in comparison to sitagliptin and cisplatin as a positive control, respectively. Among the different cells, the compounds showed the best inhibitory effects on HT-29, which was compatible with the greater expression of the dipeptidyl peptidase-4 marker detected by flow cytometry in this cell line. Further studies on the hit compounds (9e and 12c) through cell cycle and apoptosis assays also showed that these compounds could induce cell death by apoptosis or arrest cells in the G2/M phase. Accordingly, the results imply that 9e is a potent inhibitor of dipeptidyl peptidase-4 with efficient anti-cancer activity and could play a role as a cytotoxic agent in colorectal cancer.

Novel 2,4- thiazolidinediones: Synthesis, in?vitro cytotoxic activity, and mechanistic investigation

Two thiazolidinedione scaffolds different in the position of the thiazolidinedione ring in the molecule were tested for in?vitro cytotoxic activity in a panel of human cancer cell lines namely, prostate cancer cells PC-3, breast carcinoma cells MDA-MB-231

Quinazolinone-based rhodanine-3-acetic acids as potent aldose reductase inhibitors: Synthesis, functional evaluation and molecular modeling study

A series of quinazolinone-based rhodanine-3-acetic acids was synthesized and tested for in vitro aldose reductase inhibitory activity. All the target compounds displayed nanomolar activity against the target enzyme. Compounds 3a, 3b, and 3e exhibited almo

Synthesis and evaluation of quinazolin-4-ones as hypoxia-inducible factor-1α inhibitors

Quinazolin-4-one 1 was identified as an inhibitor of the HIF-1α transcriptional factor from a high-throughput screen. HIF-1α up-regulation is common in many cancer cells. In this Letter, we describe an efficient one-pot sequential reaction for the synthes