175026-96-7

Basic information

• Product Name: NQDI 1
• Synonyms: 3H-Naphtho[1,2,3-de]quinoline-1-carboxylic acid, 2,7-dihydro-2,7-dioxo-, ethyl ester;LESINURAD (RDEA-594) intermediate;2,7-Dihydro-2,7-dioxo-3H-naphtho[1,2,3-de]quinoline-1-carboxylic acid ethyl ester;NDQI 1;NQDI 1
• CAS NO: 175026-96-7
• Molecular Formula: C19H13NO4
• Molecular Weight: 319.31082
• Mol File: 175026-96-7.mol

Chemical Properties

• Melting Point: 310 °C (decomp)
• Boiling Point: 581.4±50.0 °C(Predicted)
• Appearance: orange/
• Density: 1.42±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥5mg/mL (warmed to 60° C)
• PKA: 10.76±0.40(Predicted)
• Stability: Stable for 2 years as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• CAS DataBase Reference: NQDI 1(CAS DataBase Reference)
• NIST Chemistry Reference: NQDI 1(175026-96-7)
• EPA Substance Registry System: NQDI 1(175026-96-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 175026-96-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
NQDI-1 is used as an ASK1 inhibitor for its therapeutic potential against acute ischemic renal injury. Its protective effects are mediated through the inhibition of apoptosis and oxidative stress, making it a promising candidate for the development of treatments for kidney diseases and conditions involving cell death and oxidative damage.
Used in Biotechnology Industry:
NQDI-1 is used as a tool to promote the survival of induced pluripotent stem cell populations. This application is crucial for the advancement of stem cell research and the development of regenerative medicine therapies.
Used in Neuroscience Research:
NQDI-1 is used as a neuroprotective agent to protect neurons from reactive oxygen species-induced apoptosis in a model of ischemia. This application is significant for understanding the mechanisms of neurodegenerative diseases and developing potential therapeutic strategies to combat them.

References

Volynets et al. (2011), Identification of 2H-naphtho[1,2,3-de]quinoline-2,7-diones as inhibitors of apoptosis signal-regulating kinase 1 (ASK1); Med. Chem., 54 2680 Nomura et al. (2013), An ASK1-p38 signaling pathway mediates hydrogen peroxide-induced toxicity in NG108-15 neuronal cells; Lett., 549 163 Chen et al. (2019), The MC4 receptor agonist RO27-3225 inhibits NLRP1-dependent neuronal pyroptosis via the ASK1/JNK/p38 MAPK pathway in a mouse model of intracerebral haemorrhage; J. Pharmacol., 176 1341 Ma et al. (2019), Low glucose and metformin-induced apoptosis of human ovarian cancer cells is connected to ASK1 via mitochondrial and endoplasmic reticulum stress associated pathways; Exp. Clin. Cancer Res., 38 77 Feng et al. (2018), Dual function of peroxiredoxin I in lipopolysaccharide-induced osteoblast apoptosis via reactive oxygen species and the apoptosis signal-regulating kinase 1 signaling pathway; Cell Death Discov., 4 47

Upstream product

• 82-45-1 1-amino-9,10-anthracenedione 
• 105-53-3 diethyl malonate 

Relevant articles and documents

Synthesis of 7-oxo-7H-naphtho[1,2,3-de]quinoline derivatives as potential anticancer agents active on multidrug resistant cell lines

Following our earlier finding that tetracyclic anthraquinone analogs with a fused pyridone ring exhibit cytotoxic activity toward multidrug resistant tumor cells, a series of new potential antitumor agents, 7-oxo-7H-naphtho[1,2,3-de] quinoline derivatives (3, 6-8, 10-12, 14, 15, and 18), bearing one or two basic side chains and various substituents at the pyridone ring, have been synthesized. The compounds have been obtained from 1-amino-4-chloroanthraquinone or 1-aminoanthraquinone by cyclization with diethyl malonate and the subsequent reactions of the key intermediates 2, 4, and 17. The compounds exhibited cytotoxic activity toward sensitive human leukemia cell line HL-60 and against its resistant sublines HL-60/VINC (MDR1 type) and HL-60/DX (MRP1 type).

Synthesis and cytotoxic activity of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives

A series of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidines bearing cationic side chains were prepared from aminoanthraquinones. The perimidines were prepared from 1-aminoanthraquinone by initial condensation with urea or dimethylacetamide. A series of 2-, 4-, 8-, and 11-carboxy derivatives of the dibenzisoquinolines were prepared from aminoanthraquinonecarboxylic acids. The cationic derivatives were prepared from these via amide, amine, or methylene linkers to study the effects of side chain positioning on biological activity. Within the series of carboxamide-linked compounds, the order of increasing cytotoxicity was 8- 4- 2- 11-. The 2- and 4-carboxamides showed substantial growth delays against in vivo subcutaneous colon 38 tumors in mice, but the 11-carboxamide had curative activity in this refractory model and is being investigated further.

Synthesis of novel substituted anthra [1,9-bc]pyridin-6-ones

Anthrapyridone derivative 5a was formed as a result of cyclohydrolysis of 2 which was obtained from the reaction of 1 with malononitrile, anthrapyridone 5e, 5f and 5g were also formed from cyclization reaction of the prepared new derivative 3, 4a and 4b respectively in basic conditions. While anthrapyridone derivative 5b, 5c and 5d were prepared directly from the reaction of 1 with benzylcyanide, phenyl acetaldehyde and diethyl malonate respectively.