436-72-6

Basic information

• Product Name: 5-FLUORO-4-HYDROXYQUINAZOLINE
• Synonyms: 5-FLUOROQUINAZOLIN-4-OL;5-FLUORO-4-HYDROXYQUINAZOLINE;5-FLUORO-4-HYDROXYQUNIAZOLINE;3,4-Dihydro-5-fluoro-4-oxoquinazoline;5-Fluoroquinazolin-4(3H)-one;3,4-Dihydro-5-fluoro-4-oxoquinazoline 98%;5-Fluoro-4-hydroxyquinazoline 97%;5-Fluoro-4-hydroxyquinazoline97%
• CAS NO: 436-72-6
• Molecular Formula: C₈H₅FN₂O
• Molecular Weight: 164.14
• Product Categories: blocks;Heterocycles;Quinolines;Quinoline&Isoquinoline
• Mol File: 436-72-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 238 °C
• Boiling Point: 317.5 °C at 760 mmHg
• Flash Point: 145.8 °C
• Appearance: /
• Density: 1.44 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.02±0.20(Predicted)
• CAS DataBase Reference: 5-FLUORO-4-HYDROXYQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-4-HYDROXYQUINAZOLINE(436-72-6)
• EPA Substance Registry System: 5-FLUORO-4-HYDROXYQUINAZOLINE(436-72-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-41-37/38
• Safety Statements: 26-36/37/39-39
• Hazardous Substances Data: 436-72-6(Hazardous Substances Data)

Usage

General Description

5-FLUORO-4-HYDROXYQUINAZOLINE is a synthetic chemical compound that belongs to the quinazoline family. It is a derivative of quinazoline, which is a class of aromatic organic compounds. This particular compound contains a fluorine atom at the 5 position and a hydroxyl group at the 4 position on the quinazoline ring. It has potential applications in pharmaceutical research and drug development due to its unique structure and properties. Additionally, it may have biological activities that make it useful in the treatment of certain diseases or conditions. However, further research and studies are needed to fully understand its potential uses and effects.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 115643-59-9 2-amino-6-fluorobenzamide 
• 77287-34-4 formamide 
• 64-18-6 formic acid 
• 77326-36-4 2-amino-6-fluorobenzonitrile 
• 144-62-7 oxalic acid 
• 434-76-4 2-amino-6-fluorobenzoic acid 

Downstream Products

• 135106-52-4 5-methoxy-4-(3H)-quinazolinone 
• 16499-60-8 4-chloro-5-fluoro-quinazoline 
• 1133219-01-8 3-cyclohexyl-5-fluoroquinazolin-4(3H)-one 
• 1312757-87-1 C₃₀H₃₀FN₃O₅ 
• 524954-19-6 2-chloro-4-[5-(1-methyl-piperidin-4-yloxy)-quinazolin-4-ylamino]-phenol 
• 866115-51-7 4-[5-(1-methyl-piperidin-4-yloxy)-quinazolin-4-ylamino]-phenol 

Relevant articles and documents

ERBB RECEPTOR INHIBITORS

Disclosed are compounds inhibiting ErbBs (e. g. HER2), pharmaceutically acceptable salts, hydrates, solvates or stereoisomers thereof and pharmaceutical compositions comprising the compounds. The compound and the pharmaceutical composition can effectively treat diseases associated ErbBs (especially HER2), including cancer.

Design, Synthesis, and Potency of Pyruvate Dehydrogenase Complex E1 Inhibitors against Cyanobacteria

Safe and effective algaecides are needed to control agriculturally and environmentally significant algal species. Four series (6, 10, 17, and 21) of 29 novel 4-aminopyrimidine derivatives were rationally designed and synthesized. A part of 10, 17, and 21 displayed potent inhibition of Escherichia coli pyruvate dehydrogenase complex E1 (E. coli PDHc-E1) (IC50 = 2.12-18.06 μM) and good inhibition of Synechocystis sp. PCC 6803 (EC50 = 0.7-7.1 μM) and Microcystis sp. FACH 905 (EC50 = 3.7-7.6 μM). The algaecidal activity of these compounds positively correlated with their inhibition of E. coli PDHc-E1. In particular, 21l and 10b exhibited potent algaecidal activity against PCC 6803 (EC50 = 0.7 and 0.8 μM, respectively), values that were 2-fold increased compared to that of copper sulfate (EC50 = 1.8 μM), and showed the best inhibition of cyanobacterium PDHc-E1 (IC50 = 5.10 and 6.06 μM, respectively). 17h and 21e, the best inhibitors of E. coli PDHc-E1, were studied by molecular docking, site-directed mutagenesis, and enzymatic assays. These results revealed that the improved inhibition of novel inhibitors compared with that of the lead compound I was due to the formation of a new hydrogen bond with Leu264 at the active site of E. coli PDHc-E1. The results proved the great potential to obtain effective algaecides via the rational design of PDHc-E1 inhibitors. [Figure Presented]

Synthesis and SAR optimization of quinazolin-4(3H)-ones as poly(ADP-ribose)polymerase-1 inhibitors

We have demonstrated that quinazolin-4(3H)-one, a nicotinamide (NI) mimic with PARP-1 inhibitory activity in the high micromolar range (IC50 = 5.75 μM) could be transformed into highly active derivatives with only marginal increase in molecular weight. Convenient one to two synthetic steps allowed us to explore extensive SAR at the 2-, and 5- through 8-positions of the quinazolin-4(3H)-one scaffold. Substitutions at the 2- and 8-positions were found to be most favorable for improved PARP-1 inhibition. The amino group at 8-position resulted in compound 22 with an IC50 value of 0.76 μM. Combination of the 8-amino substituent with an additional methyl substituent at the 2-position provided the most potent compound 31 [8-amino-2-methylquinazolin- 4(3H)-one, IC50 = 0.4 μM] in the present study. Compound 31 inhibited the proliferation of Brca1-deficient cells with an IC50 value of 49.0 μM and displayed >10-fold selectivity over wild type counterparts. Binding models of these derivatives within the active site of PARP-1 have further supported the SAR data and will be useful for future lead optimization efforts.