15151-57-2

Basic information

• Product Name: 2,4-DIHYDROXY-3-NITROQUINOLINE
• Synonyms: 3-NITROQUINOLINE-2,4-DIOL;3-NITROQUINOLINE-2,4-DIOL, 4-HYDROXY-3-NITRO-1H-QUINOLIN-2-ONE;3-NITRO-2,4-DIHYDROXYQUINOLINE;2,4-DIHYDROXY-3-NITROQUINOLINE;TIMTEC-BB SBB005381;3-Nitro-2,4-quinolinediol;4-Hydroxy-3-nitro-2(1H)-quinolinone;4-hydroxy-3-nitro-1H-quinolin-2-one
• CAS NO: 15151-57-2
• Molecular Formula: C₉H₆N₂O₄
• Molecular Weight: 206.15
• Mol File: 15151-57-2.mol
• Article Data: 34

Chemical Properties

• Melting Point: 225 °C (decomp)(Solv: acetic acid (64-19-7))
• Boiling Point: 309.1 °C at 760 mmHg
• Flash Point: 140.7 °C
• Appearance: /
• Density: 1.61 g/cm³
• Vapor Pressure: 0.000282mmHg at 25°C
• Refractive Index: 1.698
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 2,4-DIHYDROXY-3-NITROQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIHYDROXY-3-NITROQUINOLINE(15151-57-2)
• EPA Substance Registry System: 2,4-DIHYDROXY-3-NITROQUINOLINE(15151-57-2)

Safety Data

• Hazardous Substances Data: 15151-57-2(Hazardous Substances Data)

Usage

General Description

2,4-Dihydroxy-3-nitroquinoline is a chemical compound with the formula C9H6N2O4. It is a yellow crystalline solid that is used in the synthesis of various organic compounds and pharmaceuticals. 2,4-DIHYDROXY-3-NITROQUINOLINE has been studied for its potential biological activities, including its role as an antimicrobial and anti-inflammatory agent. Additionally, it has been investigated for its potential as a fluorescent dye for biological imaging applications. 2,4-Dihydroxy-3-nitroquinoline is a versatile compound with potential applications in various fields, making it an important target for further research and development.

InChI:InChI=1/C9H6N2O4/c12-8-5-3-1-2-4-6(5)10-9(13)7(8)11(14)15/h1-4H,(H2,10,12,13)

Upstream product

• 621-10-3 N,N'-diphenylmalonamide 
• 62-53-3 aniline 
• 70254-44-3 2,4-dihydroxyquinoline 
• 172469-70-4 5-ethyl-4-hydroxy-3-nitropyridin-2(1H)-one 
• 70254-43-2 4-Hydroxy-2-quinolone 

Downstream Products

• 132521-66-5 2,4-dichloro-3-nitroquinoline 

Relevant articles and documents

Structure-activity relationships of 4-hydroxy-3-nitroquinolin-2(1H)- ones as novel antagonists at the glycine site of N-methyl-D-aspartate receptors

A series of 4-hydroxy-3-nitroquinolin-2(1H)-ones (HNQs) was synthesized by nitration of the corresponding 2,4-quinolinediols. The HNQs were evaluated as antagonists at the glycine site of NMDA receptors by inhibition of [3H]DCKA binding to rat brain membranes. Selected HNQs were also tested for functional antagonism by electrophysiological assays in Xenopus oocytes expressing either 1a/2C subunits of NMDA receptors or rat brain AMPA receptors. The structure-activity relationships (SAR) of HNQs showed that substitutions in the 5-, 6-, and 7-positions in general increase potency while substitutions in the 8-position cause a sharp reduction in potency. Among the HNQs tested, 5,6,7-trichloro HNQ (8i) was the most potent antagonist with an IC50 of 220 nM in [3H]DCKA binding assay and a K(b) of 79 nM from electrophysiological assays. Measured under steady-state conditions HNQ 8i is 240-fold selective for NMDA over AMPA receptors. The SAR of HNQs was compared with those of 1,4-dihydroquinoxaline-2,3-diones (QXs) and 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes (QTOs). In general, HNQs have similar potencies to QXs with the same benzene ring substitution pattern but are about 10 times less active than the corresponding QTOs. HNQs are more selective for NMDA receptors than the corresponding QXs and QTOs. The similarity of the SAR of HNQs, QXs, and QTOs suggested that these three classes of antagonists might bind to the glycine site in a similar manner. With appropriate substitutions, HNQs represent a new class of potent and highly selective NMDA receptor glycine site antagonists.

Imidazo quinoline substituted phosphate agonist as well as preparation method and application thereof

The invention relates to an imidazo quinoline substituted phosphate agonist as well as a preparation method and an application thereof. Specifically, the compound disclosed by the invention has a structure as shown in a formula (I), and the definitions of all groups and substituent groups are described in the specification. The invention also discloses a preparation method of the compound and the application of the compound as a TLR agonist.

Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach

Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.

PEPTIDE-BASED VACCINES, METHODS OF MANUFACTURING, AND USES THEREOF FOR INDUCING AN IMMUNE RESPONSE

The present disclosure relates to novel peptide-based vaccines, methods of manufacturing the novel peptide-based vaccines and uses thereof for delivering peptide antigens to induce an immune response, and in particular a T cell response to a subject.