132521-66-5

Basic information

• Product Name: 2,4-DICHLORO-3-NITRO-QUINOLINE
• Synonyms: AURORA KA-4144;2,4-DICHLORO-3-NITRO-QUINOLINE;3-NITRO-2,4-DICHLORO QUINOLINE;Zinc02551827;2,4-Dichlor-3-nitro-chinolin
• CAS NO: 132521-66-5
• Molecular Formula: C₉H₄Cl₂N₂O₂
• Molecular Weight: 243.05
• Mol File: 132521-66-5.mol

Chemical Properties

• Melting Point: 102 °C(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
• Boiling Point: 359.7°C at 760 mmHg
• Flash Point: 171.3°C
• Appearance: /
• Density: 1.593g/cm³
• Vapor Pressure: 4.84E-05mmHg at 25°C
• Refractive Index: 1.693
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -4.98±0.50(Predicted)
• CAS DataBase Reference: 2,4-DICHLORO-3-NITRO-QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLORO-3-NITRO-QUINOLINE(132521-66-5)
• EPA Substance Registry System: 2,4-DICHLORO-3-NITRO-QUINOLINE(132521-66-5)

Safety Data

• Hazardous Substances Data: 132521-66-5(Hazardous Substances Data)

Usage

Uses

2,4-Dichloro-3-nitroquinoline has antitumor activity.

InChI:InChI=1/C9H4Cl2N2O2/c10-7-5-3-1-2-4-6(5)12-9(11)8(7)13(14)15/h1-4H

Upstream product

• 70254-44-3 2,4-dihydroxyquinoline 
• 15151-57-2 2,4-dihydroxy-3-nitroquinoline 
• 10025-87-3 trichlorophosphate 
• 15151-57-2 4-hydroxy-3-nitro-1,2-dihydroquinolin-2-one 

Relevant articles and documents

IMIDAZOQUINOLINE-TYPE COMPOUNDS AND USES THEREOF

Provided in the present disclosure are imidazoquinoline-type compounds, methods for their preparation, pharmaceutical compositions thereof and their use, wherein the imidazoquinoline-type compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

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.

SUBSTITUTED QUINOLINONYL PIPERAZINE COMPOUNDS USEFUL AS T CELL ACTIVATORS

Disclosed are compounds of Formula (I) or a salt thereof, wherein: R1, R2, R3, R4, R5, R6, and m are defined herein. Also disclosed are methods of using such compounds to inhibit the activi

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.

TLR7/8 AGONISTS AND LIPOSOME COMPOSITIONS

The present disclosure relates to a method of loading a toll like receptor (TLR)7/8 agonist into a liposome using remote loading and a kit of parts suitable for the loading of a TLR7/8 agonist into a liposome by said method. The present disclosure further relates to a liposome comprising a salt of a TLR7/8 agonist in the liposome interior and to the use of said liposome for stimulation of an immune response and/or treatment of a clinical condition. Finally, the present disclosure relates to a TLR7/8 agonist which is suitable for being remotely loaded into a liposome.

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.

LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES

Provided in the present disclosure are immunotherapy compounds, pharmaceutical compositions thereof and their use, wherein the immunotherapy compounds, upon local administration, form depots inducing cell mediated immune response while mitigating a systemic proinflammatory immune response.

IMIDAZOQUINOLINE COMPOUNDS AND USES THEREOF

Provided herein are imidazoquinoline derivatives, or pharmaceutically acceptable salts thereof, that are agonists of toll-like receptors 7 and 8 (TLR7/8). Also provided herein are compositions and pharmaceutical compositions comprising the imidazoquinoline derivatives, or pharmaceutically acceptable salts thereof, provided herein. Also provided herein are methods of use of the imidazoquinoline derivatives, or pharmaceutically acceptable salts thereof, provided herein to treat various diseases, such as viral, cancer, and allergic diseases, in a subject in need thereof by administering a therapeutically effective amount of the imidazoquinoline derivative, or pharmaceutically acceptable salt thereof, to the subject.

Efficacy of TLR7 agonistic imidazoquinoline as immunochemotherapeutic agent against P. Berghei ANKA infected rodent host

Malaria is a serious disease and is one of the most alarming public health issues. Plasmodium is being resistant to various antimalarials including Chloroquine (CQ) which was the first-line therapy for malaria treatment. WHO recommended several combination therapies but declining efficacy was reported to many of these therapies. Despite a great amount of research, efficient malaria vaccine still seems to be a distant dream. Immunochemotherapy could be an alternate strategy to deal with malaria. Based on the differential activity of various cytokines in the pathogenesis of and protection against malaria, the efficacy of highly active TLR7 agonistic imidazoquinoline (BBIQ) in combination with a suboptimal dose of CQ against P. berghei ANKA (PbA) in vivo was investigated. In mice treated with CQ alone, parasite appeared on Day 17 and all mice of this group died by Day 21. Whereas, mice treated with BBIQ along with CQ exhibited no appearance of parasite till Day 23. Frequencies of T cells (CD3+, CD4+and CD8+) and T regulatory cells (CD4+, CD25 +and FoxP3+) were found to be lower in brain of BBIQ + CQ treated mice as compared to BBIQ alone and CQ alone treated mice on Day 10. Inhibition of infiltration of inflammatory T cells and activation of T helper and T cytotoxic cells against the parasite was observed in the mice treated with this combination therapy. Serum levels of IFN-γ and IL-12 were found to be higher on same day in mice treated with BBIQ + CQ which revealed the generation of strong Th1 immune response in mice against the infection. Overall, TLR7 agonist acted as an efficient partner when combined with potent antimalarial drug.

ALKYL CHAIN MODIFIED IMIDAZOQUINOLINE TLR7/8 AGONIST COMPOUNDS AND USES THEREOF

Disclosed are alkyl chain modified 1H-imidazoquinoline compounds, derivatives and analogs thereof, as Toll-like receptor-7 and -8 agonists for enhancing immune responses. Also provided are methods of making pharmaceutical compositions containing these compounds. The present disclosure also describes methods of use for the alkyl chain modified 1H-imidazoquinoline compounds, derivatives and analogs thereof, and pharmaceutical compositions containing these compounds for the treatment of disease in a subject.