1920-66-7

Basic information

• Product Name: 2-CHLORO-5-NITROPYRIMIDIN-4-AMINE
• Synonyms: IFLAB-BB F1930-0037;2-CHLORO-5-NITROPYRIMIDIN-4-AMINE;4-AMINO-2-CHLORO-5-NITROPYRIMIDINE;2-CHLORO-5-NITRO-4-PYRIMIDINAMINE;4-Pyrimidinamine, 2-chloro-5-nitro-;2-Chloro-5-nitropyrimidin-4-amine ,95%;2-Chloro-5-nitro-6-aminopyrimidine;2-Chloro-5-nitropyrimidine-4-amine
• CAS NO: 1920-66-7
• Molecular Formula: C₄H₃ClN₄O₂
• Molecular Weight: 174.55
• EINECS: 217-648-7
• Product Categories: pharmacetical
• Mol File: 1920-66-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 221-226℃
• Boiling Point: 446 °C at 760 mmHg
• Flash Point: 223.5 °C
• Appearance: /Solid
• Density: 1.712 g/cm³
• Vapor Pressure: 3.79E-08mmHg at 25°C
• Refractive Index: 1.67
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -1.22±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2-CHLORO-5-NITROPYRIMIDIN-4-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5-NITROPYRIMIDIN-4-AMINE(1920-66-7)
• EPA Substance Registry System: 2-CHLORO-5-NITROPYRIMIDIN-4-AMINE(1920-66-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37-36
• WGK Germany: 3
• Hazardous Substances Data: 1920-66-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to brown solid

Uses

It is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field.

InChI:InChI=1/C4H3ClN4O2/c5-4-7-1-2(9(10)11)3(6)8-4/h1H,(H2,6,7,8)

Upstream product

• 7664-41-7 ammonia 
• 49845-33-2 2,4-Dichloro-5-nitropyrimidine 

Downstream Products

• 84928-85-8 2-methylthio-4-amino-5-nitropyrimidine 
• 304646-29-5 2-methoxy-5-nitro-pyrimidin-4-ylamine 
• 5096-84-4 N²,N²-dimethyl-5-nitro-pyrimidine-2,4-diamine 
• 5096-83-3 N²-methyl-5-nitro-pyrimidine-2,4-diamine 
• 13754-19-3 4,5-pyrimidinediamine 
• 14631-08-4 2-chloro-4,5-diaminopyrimidine 
• 14623-58-6 4,5-diamino-1H-pyrimidine-2-thione 
• 18620-73-0 2,4-diamino-5-nitropyrimidine 
• 124732-28-1 4-amino-5-nitro-2-phenylthiopyrimidine 
• 1350545-37-7 4-amino-2-(4-(4-methylpiperazin-1-yl)phenylamino)-5-nitropyrimidine 
• 1414781-77-3 N²-(4-(4-methylpiperazin-1-yl)phenyl)-5-nitropyrimidine-2,4-diamine hydrochloride 
• 1374993-31-3 2-N-(4-methylbenzyl)-5-nitropyrimidine-2,4-diamine 
• 1218-64-0 2-N-benzyl-5-nitropyrimidine-2,4-diamine 
• 1090885-32-7 2-N-(4-fluorobenzyl)-5-nitropyrimidine-2,4-diamine 

Relevant articles and documents

Sulfide Analogues of Flupirtine and Retigabine with Nanomolar KV7.2/KV7.3 Channel Opening Activity

The potassium channel openers flupirtine and retigabine have proven to be valuable analgesics or antiepileptics. Their recent withdrawal due to occasional hepatotoxicity and tissue discoloration, respectively, leaves a therapeutic niche unfilled. Metabolic oxidation of both drugs gives rise to the formation of electrophilic quinones. These elusive, highly reactive metabolites may induce liver injury in the case of flupirtine and blue tissue discoloration after prolonged intake of retigabine. We examined which structural features can be altered to avoid the detrimental oxidation of the aromatic ring and shift oxidation toward the formation of more benign metabolites. Structure–activity relationship studies were performed to evaluate the KV7.2/3 channel opening activity of 45 derivatives. Sulfide analogues were identified that are devoid of the risk of quinone formation, but possess potent KV7.2/3 opening activity. For example, flupirtine analogue 3-(3,5-difluorophenyl)-N-(6-(isobutylthio)-2-(pyrrolidin-1-yl)pyridin-3-yl)propanamide (48) has 100-fold enhanced activity (EC50=1.4 nm), a vastly improved toxicity/activity ratio, and the same efficacy as retigabine in vitro.

Design, synthesis, antitumor activity and theoretical calculation of novel PI3Ka inhibitors

PI3Kα has been identified as an ideal target to treat with PIK3CA gene mutation disease, including drugs such as Alpelisib and Copanlisib. Five purine analogues and four thiazole analogues were designed and synthesized. Their enzymatic activity against PI3Ka/β/γ/δ were tested, respectively. All compounds showed excellent selectivity in modulating PI3Ka activity, and parts of the compounds showed good inhibition. Meanwhile, we used Autodock 4.2 to explore the binding mode of the most potential compound Tg with the target protein. In addition, DFT was used to calculate the HOMO-LUMO maps of the compounds Tf, Tg and positive control. This paper will provide some useful information for further drug design of PI3Kα inhibitors.

HETEROCYCLIC-IMIDAZOLE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THEREOF, PREPARATION METHOD THEREFOR AND USE THEREOF

The present invention relates to a heterocyclic-imidazole derivative, a preparation method therefor, and a medical use thereof, and particularly to a new heterocyclic-imidazole derivative of general Formula (I), a preparation method therefor, a pharmaceutical composition comprising the same, and use thereof as a therapeutic agent, particularly as a poly(ADP-ribose)polymerase (PARP) inhibitor.