16499-65-3

Basic information

• Product Name: 4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE
• Synonyms: 4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE;AKOS A0602-0830;Quinazoline, 4-chloro-7-(trifluoroMethyl)-
• CAS NO: 16499-65-3
• Molecular Formula: C₉H₄ClF₃N₂
• Molecular Weight: 232.59
• Mol File: 16499-65-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 62-64 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 285.8 °C at 760 mmHg
• Flash Point: 126.7 °C
• Appearance: /
• Density: 1.496 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.28±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE(16499-65-3)
• EPA Substance Registry System: 4-CHLORO-7-(TRIFLUOROMETHYL)QUINAZOLINE(16499-65-3)

Safety Data

• Hazardous Substances Data: 16499-65-3(Hazardous Substances Data)

Usage

General Description

4-Chloro-7-(trifluoromethyl)quinazoline is a chemically synthesized compound recognized for its characteristic skeletal structure of quinazoline, often used as a pharmaceutical intermediate. This derivative of quinazoline is an organohalogen compound which features a trifluoromethyl group (-CF3), resulting in unique physicochemical properties such as increased chemical stability, bioavailability, and metabolic resistance. Its biological activity is often utilized in medicinal chemistry, specifically in the development of kinase inhibitors, pharmaceuticals that block certain enzymes in the treatment of cancer and inflammatory diseases. Nevertheless, the complete toxicity and safety assessment of 4-Chloro-7-(trifluoromethyl)quinazoline is not widely documented, and it is mostly handled and manipulated under controlled laboratory conditions.

InChI:InChI=1/C9H4ClF3N2/c10-8-6-2-1-5(9(11,12)13)3-7(6)14-4-15-8/h1-4H

Upstream product

• 16499-58-4 7-(trifluoromethyl)quinazolin-4(3H)-one 
• 402-13-1 2-amino-4-trifluoromethylbenzoic acid 
• 16499-58-4 4-hydroxy-7-trifluoromethylquinazoline 

Downstream Products

• 130806-75-6 3-(4''-benzylpiperazin-1''-ylmethyl)-4'-chloro-5-(7'''-trifluoromethylquinazolin-4'''-ylamino)biphenyl-2-ol 
• 130806-74-5 3-(4''-benzylpiperidin-1''-ylmethyl)-4'-chloro-5-(7'''-trifluoromethylquinazolin-4'''-ylamino)biphenyl-2-ol 
• 130806-73-4 4'-chloro-3-(4''-methylpiperidin-1''-ylmethyl)-5-(7'''-trifluoromethylquinazolin-4'''-ylamino)biphenyl-2-ol 
• 130806-72-3 4'-chloro-3-(piperidin-1''-ylmethyl)-5-(7'''-trifluoromethylquinazolin-4'''-ylamino)biphenyl-2-ol 
• 130806-71-2 4'-chloro-3-(pyrrolidin-1''-ylmethyl)-5-(7''-trifluoromethylquinazolin-4''-ylamino)biphenyl-2-ol 
• 130806-69-8 4'-chloro-3-diethylaminomethyl-5-(7''-trifluoromethylquinqzolin-4''-ylamino)biphenyl-2-ol 
• 130806-70-1 3-(t-butylaminomethyl)-4'-chloro-5-(7''-trifluoromethylquinazolin-4''-ylamino)biphenyl-2-ol 
• 129190-40-5 2,6-bis(4'-benzylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-32-5 2,6-bis(dipentylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 
• 129190-38-1 2,6-bis(3',5'-dimethylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-37-0 2,6-bis(4'-methylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-36-9 2,6-bis(3'-methylpiperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-35-8 2,6-bis(piperidin-1'-ylmethyl)-4-(7''-trifluoromethylquinazolin-4''-ylamino)phenol 
• 129190-30-3 2,6-bis(dipropylaminomethyl)-4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol 

Relevant articles and documents

Drug-like property optimization: Discovery of orally bioavailable quinazoline-based multi-targeted kinase inhibitors

In an effort to develop new cancer therapeutics, we have reported clinical candidate BPR1K871 (1) as a potent anticancer compound in MOLM-13 and MV4-11 leukemia models, as well as in colorectal and pancreatic animal models. As BPR1K871 lacks oral bioavailability, we continued searching for orally bioavailable analogs through drug-like property optimization. We optimized both the physicochemical properties (PCP) as well as in vitro rat liver microsomal stability of 1, with concomitant monitoring of aurora kinase enzyme inhibition as well as cellular anti-proliferative activity in HCT-116 cell line. Structural modification at the 6- and 7-position of quinazoline core of 1 led to the identification of 34 as an orally bioavailable (F% = 54) multi-kinase inhibitor, which exhibits potent anti-proliferative activity against various cancer cell lines. Quinazoline 34 is selected as a promising oral lead candidate for further preclinical evaluation.

Potential Antimalarials. IX Di-Mannich Bases of 4-(7'-Trifluoromethylquinazolin-4'-ylamino)phenol and 4-(7'-Trifluoromethylquinolin-4'-ylamino)phenol

Syntheses are reported for a series of di-Mannich bases of 4-(7'-trifluoromethylquinazolin-4'-ylamino)phenol derived from 4-chloro-7-trifluoromethylquinazoline with the di-Mannich bases of 4-aminophenol.Some analogous quinolines were prepared similarly.When tested for antimalarial activity against Plasmodium falciparum in vitro, the quinazolines were rather less active than the corresponding quinolines.