58421-79-7

Basic information

• Product Name: 4-CHLORO-6-METHYLQUINAZOLINE
• Synonyms: AKOS BBS-00000251;4-CHLORO-6-METHYLQUINAZOLINE;IFLAB-BB F1244-0099;CHEMBRDG-BB 7188065
• CAS NO: 58421-79-7
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 178.62
• Mol File: 58421-79-7.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-CHLORO-6-METHYLQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6-METHYLQUINAZOLINE(58421-79-7)
• EPA Substance Registry System: 4-CHLORO-6-METHYLQUINAZOLINE(58421-79-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 58421-79-7(Hazardous Substances Data)

Usage

General Description

4-CHLORO-6-METHYLQUINAZOLINE is a compound with the chemical formula C9H7ClN2. It is a quinazoline derivative with a chloro and methyl substituent at the 4 and 6 positions, respectively. 4-CHLORO-6-METHYLQUINAZOLINE is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential biological activities, including its use as an antifungal and antibacterial agent. Its chemical structure and properties make it suitable for various applications in the pharmaceutical and agrochemical industries.

Upstream product

• 19181-53-4 6-methyl-3H-quinazolin-4-one 
• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 77287-34-4 formamide 
• 19181-53-4 6-methyl-4-hydroxyquinazoline 
• 40545-33-3 2-amino-5-methylbenzamide 

Downstream Products

• 92554-57-9 6-methyl-N-phenylquinazolin-4-amine 
• 1259017-75-8 2-((4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-quinazolin-6-yl)methyl)isoindoline-1,3-dione 
• 1259017-77-0 2-((4-(3-chloro-4-fluorophenylamino)quinazolin-6-yl)methyl)isoindoline-1,3-dione 
• 1259017-78-1 2-((4-(3-bromophenylamino)quinazolin-6-yl)methyl)-isoindoline-1,3-dione 

Relevant articles and documents

Discovery of quinazolinyl-containing benzamides derivatives as novel HDAC1 inhibitors with in vitro and in vivo antitumor activities

A series of quinazolinyl-containing benzamide derivatives were designed, synthesized and evaluated for their in vitro histone deacetylase 1 (HDAC1) inhibitory activities. Compounds 11a surpassed the known class I selective HDAC inhibitor MS-275 in both HDAC1 enzymatic inhibitory activity and cellular anti-proliferative activity against a selected set of cancer cell types (Hut78, K562, Hep3B and HCT116 cells) with no observed effects on human normal cells. In particular, compound 11a inhibited HDAC1 over the other tested HDACs isoforms (HDAC2, HDAC6 and HDAC8) with acceptable safety profiles. Moreover, compound 11a displayed favorable oral pharmacokinetic properties and showed significant antitumor activity in the A549 tumor xenograft model in vivo.

Design, Synthesis and Bioevaluation of Two Series of 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines

Two series of 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-ones and N-(1-benzylpiperidin-4-yl)quinazolin-4-amines were designed initially as potential acetylcholine esterase inhibitors. Biological evaluation demonstrated that N-(1-benzylpiperidin-4-yl)quinazolin-4-amines significantly inhibited AChE activity. Especially, two compounds of them were found to be the most potent with relative AChE inhibition percentages of 87 percent in comparison to donepezil. The docking studies with AChE showed similar interactions between donepezil and four derivatives. N-(1-Benzylpiperidin-4-yl)quinazolin-4-amines also exhibited significant DPPH scavenging effects. The two series of compound also exerted moderate to good cytotoxicity against three human cancer cell lines, including SW620 (human colon cancer), PC-3 (prostate cancer), and NCI?H23 (lung cancer), with 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one being the most cytotoxic agent. 3-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one significantly induced early apoptosis and arrested the SW620 cells at G2/M phase. From this study, two compounds of N-(1-benzylpiperidin-4-yl)quinazolin-4-amines could serve as new leads for further design and AChE inhibitors, while 3-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]quinazolin-4(3H)-one could serve as a new lead for the design and development of more potent anticancer agents.

Design, synthesis and biological evaluation of novel histone deacetylase inhibitors incorporating 4-aminoquinazolinyl systems as capping groups

A series of hydroxamic acid-based HDACIs with 4-aminoquinazolinyl moieties as capping groups was profiled. Most compounds showed more potent HDACs inhibition activity than clinically used drug SAHA. Among them, compounds 5f and 5h selectively inhibited HDAC 1,2 over HDAC8, and showed strong activity in several cellular assays, not possessing significant toxicity to primary human cells and hERG inhibition. Strikingly, 5f possessed acceptable pharmacokinetic characteristics and exhibited significant antitumor activity in an A549 xenograft model study at well tolerated doses.