Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H6N2O |
| Molecular Weight | 146.146 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1N=CNC2=C1C=CC=C2
InChI
InChIKey=QMNUDYFKZYBWQX-UHFFFAOYSA-N
InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16337154 | https://www.ncbi.nlm.nih.gov/pubmed/16202158
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16337154 | https://www.ncbi.nlm.nih.gov/pubmed/16202158
4-Hydroxyquinazoline is been used to inhibit PARP (poly(ADP-ribose) synthetase) which catalyzes covalent attachment of the ADP-ribose moiety of NAD+ to various proteins. This compound specifically and potently inhibits PARP-1. 4-HQN demonstrates the ability to decrease activation of transcription factor NFκB and AP-1 in lipopolysaccharide-induced shock. Mechanistic studies indicate that 4-HQN activates PI3-kinase/Akt pathway in the liver, spleen, and lung and down-regulates two elements of the MAP kinase system. Additionally, this agent has been observed to decrease ischemia-reperfusion-induced increase of protein oxidation, single-strand DNA breaks, lipid peroxidation, and mitochondrial reactive oxygen species production in the reperfusion period.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis, biological evaluation and molecular docking of novel series of spiro [(2H,3H) quinazoline-2,1'- cyclohexan]-4(1H)- one derivatives as anti-inflammatory and analgesic agents. | 2010-06 |
|
| Diversity-oriented synthesis of benzimidazole, benzoxazole, benzothiazole and quinazolin-4(3H)-one libraries via potassium persulfate-CuSO4-mediated oxidative coupling reactions of aldehydes in aqueous micelles. | 2010-05 |
|
| A combined LS-SVM & MLR QSAR workflow for predicting the inhibition of CXCR3 receptor by quinazolinone analogs. | 2010-05 |
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| Quinazolinone linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates: Design, synthesis and biological evaluation as potential anticancer agents. | 2010-01-15 |
|
| Preparation and optimization of iridium complexes with quinazolinone ligands on solid supports. | 2009-10-09 |
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| Optimization of a series of quinazolinone-derived antagonists of CXCR3. | 2009-09-01 |
|
| A straightforward total synthesis of (-)-chaetominine. | 2009-08-10 |
|
| Baseline sensitivity to proquinazid in Blumeria graminis f. sp. tritici and Erysiphe necator and cross-resistance with other fungicides. | 2009-08 |
|
| Rapid and efficient synthesis of 4(3H)-quinazolinones under ultrasonic irradiation using silica-supported Preyssler nanoparticles. | 2009-08 |
|
| KIF11 inhibition for glioblastoma treatment: reason to hope or a struggle with the brain? | 2009-06-22 |
|
| Environmentally friendly iron-catalyzed cascade synthesis of 1,2,4-benzothiadiazine 1,1-dioxide and quinazolinone derivatives. | 2009-06-10 |
|
| Substituted quinazolines, part 3. Synthesis, in vitro antitumor activity and molecular modeling study of certain 2-thieno-4(3H)-quinazolinone analogs. | 2009-06 |
|
| The triple combination of tenofovir, emtricitabine and efavirenz shows synergistic anti-HIV-1 activity in vitro: a mechanism of action study. | 2009-05-13 |
|
| Degradation and detoxification of disperse dye Scarlet RR by Galactomyces geotrichum MTCC 1360. | 2009-04 |
|
| Quantitative structure-activity relationship study of serotonin (5-HT7) receptor inhibitors using modified ant colony algorithm and adaptive neuro-fuzzy interference system (ANFIS). | 2009-04 |
|
| New pyrazoline bearing 4(3H)-quinazolinone inhibitors of monoamine oxidase: synthesis, biological evaluation, and structural determinants of MAO-A and MAO-B selectivity. | 2009-01-15 |
|
| One-pot synthesis of quinazolinone derivatives from nitro-compounds with the aid of low-valent titanium. | 2009-01-13 |
|
| Hemodynamic and cardiac neurotransmitter-releasing effects in conscious dogs of attention- and wake-promoting agents: a comparison of d-amphetamine, atomoxetine, modafinil, and a novel quinazolinone H3 inverse agonist. | 2009-01 |
|
| Synthesis and anti-inflammatory activity of newer quinazolin-4-one derivatives. | 2009-01 |
|
| Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives. | 2008-12-21 |
|
| Synthesis and evaluation of structurally constrained quinazolinone derivatives as potent and selective histamine H3 receptor inverse agonists. | 2008-11-13 |
|
| Stereoelectronic properties of spiroquinazolinones in differential PDE7 inhibitory activity. | 2008-09 |
|
| Synthesis, structure-activity relationships, and biological profiles of a quinazolinone class of histamine H3 receptor inverse agonists. | 2008-08-14 |
|
| Crystal structure of HsEg5 in complex with clinical candidate CK0238273 provides insight into inhibitory mechanism, potency, and specificity. | 2008-08-08 |
|
| Inhibition of mammalian aspartate transcarbamylase by quinazolinone derivatives. | 2008-08 |
|
| Synthesis and cytotoxicity testing of novel 2-(3-substituted-6-chloro-1,1-dioxo-1,4,2-benzodithiazin-7-yl)-3-phenyl-4(3H)-quinazolinones. | 2008-08 |
|
| Synthesis of some new quinazolin-4-one derivatives and evaluation of their antimicrobial and antiinflammatory effects. | 2008-06-10 |
|
| A three component one-pot procedure for the synthesis of [1,2,4]triazolo/benzimidazolo-quinazolinone derivatives in the presence of H6P2W18O(62).18H2O as a green and reusable catalyst. | 2008-06-05 |
|
| Synthesis, analgesic and anti-inflammatory evaluation of some new 3H-quinazolin-4-one derivatives. | 2008-06 |
|
| Novel quinazolinone derivatives as 5-HT7 receptor ligands. | 2008-03-01 |
|
| Tumor-targeting nanodelivery enhances the anticancer activity of a novel quinazolinone analogue. | 2008-03 |
|
| Design and synthesis of novel potent and selective integrin alphanubeta3 antagonists--novel synthetic routes to isoquinolinone, benzoxazinone, and quinazolinone acetates. | 2008-01-15 |
|
| Synthesis and anticonvulsant activity of some quinazolin-4-(3H)-one derivatives. | 2008 |
|
| Microwave-assisted synthesis of bioactive quinazolines and quinazolinones. | 2007-12 |
|
| Synthesis and antimicrobial activities of some novel substituted 2-imidazolyl-N-(4-oxo-quinazolin-3(4H)-yl)-acetamides. | 2007-11 |
|
| Regulation of poly(ADP-ribose) polymerase-1 (PARP-1) gene expression through the post-translational modification of Sp1: a nuclear target protein of PARP-1. | 2007-10-25 |
|
| Quinazolinone derivatives as orally available ghrelin receptor antagonists for the treatment of diabetes and obesity. | 2007-10-18 |
|
| Rational design of conformationally restricted quinazolinone inhibitors of poly(ADP-ribose)polymerase. | 2007-10-15 |
|
| Pharmacological characterization of a novel nonpeptide antagonist for formyl peptide receptor-like 1. | 2007-10 |
|
| Synthesis and biological properties of 4-(3H)-quinazolone derivatives. | 2007-09 |
|
| [Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives bearing dithiocarbamate chains]. | 2007-07 |
|
| Systematic effect of benzo-annelation on oxo-hydroxy tautomerism of heterocyclic compounds. Experimental matrix-isolation and theoretical study. | 2007-06-14 |
|
| Synthesis and structure-activity relationships of 3H-quinazolin-4-ones and 3H-pyrido[2,3-d]pyrimidin-4-ones as CXCR3 receptor antagonists. | 2007-06 |
|
| Quinazolinone fungal efflux pump inhibitors. Part 3: (N-methyl)piperazine variants and pharmacokinetic optimization. | 2007-05-15 |
|
| A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives. | 2007-03-29 |
|
| Preclinical selection of a novel poly(ADP-ribose) polymerase inhibitor for clinical trial. | 2007-03 |
|
| Molecular-docking-guided design, synthesis, and biologic evaluation of radioiodinated quinazolinone prodrugs. | 2007-02-22 |
|
| A fluorescent chemical sensor for Fe3+ based on blocking of intramolecular proton transfer of a quinazolinone derivative. | 2007-01-15 |
|
| Synthesis and antifungal bioactivities of 3-alkylquinazolin- 4-one derivatives. | 2006-06-12 |
|
| Synthesis of new 4(3H)-quinazolinone derivatives using 5(4H)-oxazolones. | 2006-05-27 |
Sample Use Guides
Rats were treated with 4-Hydroxyquinazoline at a sublethal dose level (2 mg/Kg)
Route of Administration:
Oral
H9c2(2-1) cardiomyoblasts were incubated without (negative control) and with 1 mM hydrogen peroxide for 3 h either untreated (positive control) or treated with 4-hydroxyquinazoline (in 5, 10, 50, 100 and 200 mM) or HO-3089 (in 0.02, 0.05, 0.1, 10 and 50 mM). At the end of the incubation period the survival of cells was determined by the MTT assay
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Quinazolinone
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491-36-1
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DTXSID8049412
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207-735-8
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135408753
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84JOT4EY5X
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5863
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SUBSTANCE RECORD
