20872-93-9

Basic information

• Product Name: 7-NITRO-3H-QUINAZOLIN-4-ONE
• Synonyms: 7-NITRO-3H-QUINAZOLIN-4-ONE;7-NITRO-4(1H)-QUINAZOLINONE;7-NITRO-4-HYDROXYQUINONAZOLINE;7-NITRO-4-QUINAZOLINOL;4(1H)-Quinazolinone, 7-nitro-;7-Nitroquinazolin-4-ol;7-Nitroquinazolin-4(1H)-one, 7-Nitroquinazolin-4-ol;7-Nitroquinazolin-4(3H)-one
• CAS NO: 20872-93-9
• Molecular Formula: C₈H₅N₃O₃
• Molecular Weight: 191.14
• Product Categories: pharmacetical
• Mol File: 20872-93-9.mol
• Article Data: 36

Chemical Properties

• Melting Point: 276 °C
• Boiling Point: 381.3 °C at 760 mmHg
• Flash Point: 184.4 °C
• Appearance: /
• Density: 1.64 g/cm³
• Vapor Pressure: 5.12E-06mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.72±0.20(Predicted)
• CAS DataBase Reference: 7-NITRO-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-NITRO-3H-QUINAZOLIN-4-ONE(20872-93-9)
• EPA Substance Registry System: 7-NITRO-3H-QUINAZOLIN-4-ONE(20872-93-9)

Safety Data

• Hazardous Substances Data: 20872-93-9(Hazardous Substances Data)

Usage

General Description

7-Nitro-3H-quinazolin-4-one is a chemical compound that belongs to the quinazoline family. It is a yellow crystalline solid that is used in the synthesis of various pharmaceutical compounds and as a building block in organic chemistry. 7-NITRO-3H-QUINAZOLIN-4-ONE is known for its potential biological activities, including antifungal, antitumor, and antimicrobial properties. It is also used as a reagent in chemical reactions and as a precursor for the synthesis of other nitrogen-containing heterocycles. Its unique structure and diverse reactivity make it a valuable compound in medicinal chemistry and drug discovery research.

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

Upstream product

• 19815-17-9 4-chloro-7-nitroquinazoline 
• 19815-14-6 7-nitroquinazolin-4-amine 
• 77287-34-4 formamide 
• 619-17-0 4-Nitroanthranilic acid 
• 64392-62-7 formamidinium acetate 
• 6313-33-3 formamidine hydrochloride 
• 31930-18-4 2-amino-4-nitrobenzamide 
• 149-73-5 trimethyl orthoformate 
• 3473-63-0 formamidine acetic acid 
• 67-56-1 methanol 
• 122-51-0 orthoformic acid triethyl ester 
• 463-52-5 formamidine 

Downstream Products

• 90004-09-4 7?aminoquinazolin?4(3H)?one 
• 19815-17-9 4-chloro-7-nitroquinazoline 
• 591755-13-4 3-benzyl-7-nitroquinazolin-4(3H)-one 
• 591755-15-6 7-amino-3-benzylquinazolin-4(3H)-one 
• 344455-12-5 [2-(4-chloro-phenyl)-ethyl]-(7-nitro-quinazolin-4-yl)-amine 
• 49565-62-0 2-(methylamino)-4-nitro-benzoic acid 
• 857759-32-1 7-nitro-4-phenoxy-quinazoline 
• 90004-09-4 7-aminoquinazolin-4-one 

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.

Self-catalyzed phototandem perfluoroalkylation/cyclization of unactivated alkenes: Synthesis of perfluoroalkyl-substituted quinazolinones

A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (Rf = CF3, C3F7, C4F9, C6F13, C8F17) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.

Synthesis and evaluation of new 4(3H)-Quinazolinone derivatives as potential anticancer agents

A series of new 4(3H)-quinazolinones were synthesized and evaluated for their cytotoxic activity against a set of human cancer cell lines MDA-MB-231 and MCF-7 (breast), HCT-116 and HT-29 (colon) and A549 (lung). Among the tested compounds, 22a exhibited p