6943-17-5

Basic information

• Product Name: 6-NITROQUINAZOLIN-4(3H)-ONE
• Synonyms: 6-NITRO-4(1H)-QUINAZOLINONE;6-NITRO-4(3H)-QUINAZOLINONE;6-NITRO-4-QUINAZOLONE;6-NITROQUINAZOLIN-4(3H)-ONE;6-NITROQUINAZOLIN-4-OL;6-nitro-3,4-dihydroquinazolin-4-one;6-Nitro-3H-quinazolin-4-one;NSC 51669
• CAS NO: 6943-17-5
• Molecular Formula: C₈H₅N₃O₃
• Molecular Weight: 191.14
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6943-17-5.mol
• Article Data: 78

Chemical Properties

• Melting Point: 286-287 °C
• Boiling Point: 406.989 °C at 760 mmHg
• Flash Point: 199.94 °C
• Appearance: Yellow Solid
• Density: 1.642 g/cm³
• Vapor Pressure: 7.81E-07mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: -1.01±0.20(Predicted)
• CAS DataBase Reference: 6-NITROQUINAZOLIN-4(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-NITROQUINAZOLIN-4(3H)-ONE(6943-17-5)
• EPA Substance Registry System: 6-NITROQUINAZOLIN-4(3H)-ONE(6943-17-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6943-17-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C8H5N3O3/c12-8-6-3-5(11(13)14)1-2-7(6)9-4-10-8/h1-4H,(H,9,10,12)

Upstream product

• 49675-68-5 4-amino-6-nitroquinazoline 
• 77287-34-4 formamide 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 16313-65-8 2-amino-5-nitrobenzamide 
• 149-73-5 trimethyl orthoformate 
• 17420-30-3 5-nitroanthranilonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 19230-50-3 2-iodo-5-nitro-benzoic acid 
• 6313-33-3 formamidine hydrochloride 
• 122-51-0 orthoformic acid triethyl ester 
• 64-18-6 formic acid 
• 50-00-0 formaldehyd 
• 491-36-1 4-quinazolinol 
• 3473-63-0 formamidine acetic acid 

Downstream Products

• 16064-13-4 6-nitro-3-methyl-quinazolin-4-one 
• 19815-16-8 4-chloro-6-nitro-quinazoline 
• 17329-31-6 6-amino-3H-quinazolin-4-one 
• 874497-66-2 6-nitro-4-phenoxy-quinazoline 
• 591755-12-3 3-benzyl-6-nitroquinazolin-4-one 
• 900513-13-5 3-(4-methoxybenzyl)-6-nitroquinazolin-4-(3H)-one 
• 169205-64-5 N-benzyl-6-nitroquinazolin-4-amine 
• 184356-50-1 4-(3'-chloro-4'-fluoroanilino)-6-nitroquinazoline 
• 851653-35-5 [3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-nitro-quinazolin-4-yl)-amine 
• 184356-51-2 4-(3'-chloro-4'-fluoroanilino)-6-aminoquinazoline 
• 845271-71-8 N⁴-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-quinazoline-4,6-diamine 
• 591755-22-5 3-benzyl-5-bromo-6-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)quinazolin-4(3H)-one 
• 1451544-48-1 4-(4-(2-(diethylamino)acetamido)anilino)-6-nitroquinazoline 
• 1454806-13-3 4-(3-chloro-4-(2-(diethylamino)acetamido)anilino)-6-nitroquinazoline 

Relevant articles and documents

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

Isoxazole formamido-4 (3H)-quinazolinone derivative as well as synthesis method and application thereof

The invention relates to a 6-(isoxazolyl-3-formamido)-4 (3H)-quinazolinone derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituent groups. The invention discloses structures and synthesis methods of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activity of protein tyrosine phosphatase, and the compounds can be further developed into drugs for treating Alzheimer's disease.

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.