16064-10-1

Basic information

• Product Name: 6-HYDROXY-3,4-DIHYDROQUINAZOLONE
• Synonyms: 6-HYDROXYQUINAZOLIN-4(3H)-ONE;6-HYDROXY-3,4-DIHYDROQUINAZOLONE;3,4-Dihydro-6-hydroxy-4-oxoquinazoline;3,4-Dihydro-6-hydroxy-4-oxoquinazoline 98%;6-hydroxy-4-quinazolinone;6-Hydroxy-4-quinazolone;6-hydroxyquinazolin-4-ol;3,4-Dihydro-6-hydroxyquinazolin-4-one
• CAS NO: 16064-10-1
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.15
• Product Categories: blocks;Heterocycles;Quinolines;Quinolines, Quinazolines and derivatives
• Mol File: 16064-10-1.mol

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 416°C at 760mmHg
• Flash Point: 205.4°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 1.64E-07mmHg at 25°C
• Refractive Index: 1.706
• PKA: 9.37±0.20(Predicted)
• CAS DataBase Reference: 6-HYDROXY-3,4-DIHYDROQUINAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXY-3,4-DIHYDROQUINAZOLONE(16064-10-1)
• EPA Substance Registry System: 6-HYDROXY-3,4-DIHYDROQUINAZOLONE(16064-10-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 16064-10-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-HYDROXY-3,4-DIHYDROQUINAZOLONE is used as an intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure and reactivity. It plays a crucial role in the development of new drugs and medicinal compounds, contributing to advancements in healthcare.
Used in Organic Synthesis:
In the field of organic synthesis, 6-HYDROXY-3,4-DIHYDROQUINAZOLONE is utilized as a key building block for the creation of complex organic molecules. Its versatility in chemical reactions allows for the synthesis of a wide range of organic compounds, expanding the scope of chemical research and development.
Used in Antimicrobial Applications:
6-HYDROXY-3,4-DIHYDROQUINAZOLONE is employed as an antimicrobial agent, leveraging its biological activity to combat various microorganisms. This property makes it a valuable component in the development of new antimicrobial drugs and treatments, addressing the growing need for effective solutions against resistant pathogens.
Used in Anti-Inflammatory Applications:
6-HYDROXY-3,4-DIHYDROQUINAZOLONE is also used as an anti-inflammatory agent, capitalizing on its ability to reduce inflammation and alleviate symptoms associated with inflammatory conditions. This application contributes to the development of new therapeutic options for various inflammatory diseases, improving patient care and outcomes.
Overall, 6-HYDROXY-3,4-DIHYDROQUINAZOLONE's diverse applications across different industries highlight its importance and potential in the field of chemistry and medicine.

InChI:InChI=1/C8H6N2O2/c11-5-1-2-7-6(3-5)8(12)10-4-9-7/h1-4,11H,(H,9,10,12)

Upstream product

• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 77287-34-4 formamide 
• 67-56-1 methanol 
• 3473-63-0 formamidine acetic acid 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 182880-24-6 6-Hydroxy-4-methoxyquinazoline 
• 1012054-60-2 2-(4-(3-chloro-4-fluorophenylamino)quinazolin-6-yloxy)-N-hydroxyacetamide 
• 1012057-27-0 ethyl 2-(4-(3-chloro-4-fluorophenylamino)quinazolin-6-yloxy)acetate 
• 1012057-68-9 (R)-4-(1-phenylethylamino)quinazolin-6-ol 
• 1012057-69-0 (R)-4-(1-phenylethylamino)quinazolin-6-yl acetate 
• 1012057-70-3 (R)-ethyl 6-(4-(1-phenylethylamino)quinazolin-6-yloxy)hexanoate 
• 1012057-71-4 ethyl (R)-7-(7-methoxy-4-((1-phenylethyl)amino)quinazolin-6-yloxy)heptanoate 

Relevant articles and documents

The monoamine oxidase inhibition properties of C6-mono- and N3/C6-disubstituted derivatives of 4(3H)-quinazolinone

Parkinson's disease is characterised by the death of the nigrostriatal neurons and depletion of striatal dopamine. The standard symptomatic therapy consists of dopamine replacement with L-dopa, the metabolic precursor of dopamine, which represents the most effective treatment. Since monoamine oxidase (MAO) B is a key dopamine metabolising enzyme in the brain, MAO-B inhibitors are often used as adjuvants to L-dopa. In addition to the symptomatic benefits offered by MAO-B inhibitors, these drugs may also possess neuroprotective properties and possibly delay the progression of Parkinson's disease. Based on the therapeutic use of MAO-B inhibitors, the present study evaluates a series of mono- and disubstituted derivatives of 4(3H)-quinazolinone as potential inhibitors of recombinant human MAO-A and MAO-B. Twelve C6-monosubstituted and nine N3/C6-disubstituted 4(3H)-quinazolinone derivatives were synthesised, which led to the discovery of novel quinazolinone derivatives with micromolar and submicromolar activities as inhibitors of MAO-B. The most potent mono- and disubstituted derivatives exhibited IC50 values of 6.35 μM (7f) and 0.685 μM (8b), respectively. This study identifies suitable substitution patterns for the design of 4(3H)-quinazolinone derivatives as MAO-B inhibitors.

6-Nitro-Quinazolin?4(3H)?one Exhibits Photodynamic Effects and Photodegrades Human Melanoma Cell Lines. A Study on the Photoreactivity of Simple Quinazolin?4(3H)?ones

Photochemo and photodynamic therapies are minimally invasive approaches for the treatment of cancers and powerful weapons for competing bacterial resistance to antibiotics. Synthetic and naturally occurring quinazolinones are considered privileged anticancer and antibacterial agents, with several of them to have emerged as commercially available drugs. In the present study, applying a single-step green microwave irradiation mediated protocol we have synthesized eleven quinazolinon?4(3H)?ones, from cheap readily available anthranilic acids, in very good yields and purity. These products were irradiated in the presence of pBR322 plasmid DNA under UVB, UVA and visible light. Four of the compounds proved to be very effective DNA photocleavers, at low concentrations, being time and concentration dependent as well as pH independent. Participation of reactive oxygen species was related to the substitution of quinazolinone derivatives. 6-Nitro-quinazolinone in combination with UVA irradiation was found to be in vitro photodestructive for three cell lines; glioblastoma (U87MG and T98G) and mainly melanoma (A?375). Thus, certain appropriately substituted quinazolinones may serve as new lead photosensitizers for the development of promising biotechnological applications and as novel photochemo and photodynamic therapeutics.

HER2 Kinase-Targeted Breast Cancer Therapy: Design, Synthesis, and in Vitro and in Vivo Evaluation of Novel Lapatinib Congeners as Selective and Potent HER2 Inhibitors with Favorable Metabolic Stability

HER2 kinase as a well-established target for breast cancer (BC) therapy is associated with aggressive clinical outcomes; thus, herein we present structural optimization for HER2-selective targeting. HER2 profiling of the developed derivatives demonstrated

As Aurora kinase inhibitors of the substituted quinazoline derivatives

The invention relates to a substituted quinazoline derivative as an aurora kinase inhibitor, which is shown as structural formula (I) or (Ia), tautomers, hydrates, solvates or pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising the tautomers, hydrates, solvates and pharmaceutically acceptable salts as drug active ingredients, and application of the compounds and the pharmaceutical compositions in preparation of medicines for protection, treatment, curing or alleviation of proliferative diseases of patients.

Synthesis and biological evaluation of novel quinazoline-4-piperidinesulfamide derivatives as inhibitors of NPP1

The ecto-nucleotide pyrophosphatase/phosphodiesterase-1 (NPP1) was recently shown to promote mineralization of the aortic valve, hence, its inhibition represents a significant target. A quinazoline-4-piperidine sulfamide compound (QPS1) has been described as a specific and non-competitive inhibitor of NPP1. We report herein the synthesis and in vitro inhibition studies of novel quinazoline-4-piperidine sulfamide analogues using QPS1 as the lead compound. Of the 26 derivatives prepared, four compounds were found to have Ki 105 nM against human NPP1.

Kuikui zuo lin kind of target anti- tumor compound and its preparation method and application (by machine translation)

The present invention provides a chemical formula (I) indicated by the kuikui zuo lin kind of target anti- tumor compound and its preparation method, in particular to EGFR, HER - 2 and DNA multi-target anti- tumor compounds, also provides a method for preparing the same and in the application of the anti-tumor medicament. Studies show that the compounds of the invention have significant anti-tumor activity, metabolic stability relative to the reference substance EMB - 3 is improved notably. (by machine translation)

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.

Novel EGFR inhibitors prepared by combination of dithiocarbamic acid esters and 4-anilinoquinazolines

On the basis of combination strategy, a novel series of EGFR inhibitors were designed and synthesized by combination of dithiocarbamic acid esters and 4-anilinoquinazolines. The effect of the synthesized compounds on cell proliferation was evaluated by MTT assay in three human cancer cell lines: MDA-MB-468, SK-BR-3 and HCT-116. Two compounds (11d and 11f) were found more potent against all three cell lines and five compounds (11a, 11d-11g) were found more potent against both MDA-MB-468 and SK-BR-3 than Lapatinib. SAR studies revealed that the substituents on C6 and C7 positions of quinazoline, the amine component of dithiocarbamate moiety and the linker greatly affected the activity. This work provides a promising new strategy for the preparation of potent tyrosine kinase inhibitors.

Discovery and structure-activity relationships of a novel class of quinazoline glucokinase activators

We describe design, syntheses and structure-activity relationships of a novel class of 4,6-disubstituted quinazoline glucokinase activators. Prototype quinazoline leads (4 and 5) were designed based on the X-ray analyses of the previous 2-aminobenzamide lead classes. Modifications of the quinazoline leads led to the identification of a potent GK activator (21d).

Discovery of boron-conjugated 4-anilinoquinazoline as a prolonged inhibitor of EGFR tyrosine kinase

Boron-conjugated 4-anilinoquinazolines were designed and synthesized as inhibitors of EGFR tyrosine kinase with possible covalent bond interactions between the boron atom and the nucleophilic groups of the EGFR kinase domain. Among the compounds synthesized, compounds 6c, 7b, and 7d reduced the EGF-mediated phosphorylation of EGFR tyrosine kinase and its downstream kinases including ERK and Akt in A431 cells. The cell growth was inhibited by these compounds through arrest of G1 cell cycle, which induced apoptosis. A time-dependent in vitro preincubation assay demonstrated the irreversible inhibition of compound 7d against EGFR tyrosine kinase. Quantum mechanical docking simulation revealed that the boronic acid moiety of compound 7d formed a covalent B-O bond with Asp800 in addition to hydrogen bonds with Asp800 and Cys797, which may cause the prolonged inhibition of compound 7d toward EGFR tyrosine kinase.