1920-66-7

Usage

Uses

Used in Organic Synthesis:
2-CHLORO-5-NITROPYRIMIDIN-4-AMINE is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Agrochemical Industry:
In the agrochemical field, 2-CHLORO-5-NITROPYRIMIDIN-4-AMINE is utilized as a vital component in the production of pesticides and other agrochemical products, helping to improve crop protection and yield.
Used in Pharmaceutical Industry:
2-CHLORO-5-NITROPYRIMIDIN-4-AMINE plays a significant role as an intermediate in the synthesis of pharmaceutical drugs, aiding in the development of new medications and therapies to treat various diseases and conditions.
Used in Dyestuff Industry:
2-CHLORO-5-NITROPYRIMIDIN-4-AMINE is also employed as a raw material in the dyestuff industry, where it contributes to the creation of various dyes and pigments used in coloring textiles, plastics, and other materials.

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

Upstream product

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

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 
• 84928-86-9 2-phenyl-4-amino-5-nitropyrimidine 
• 1374993-32-4 5-nitro-2-N-(2-phenylethyl)pyrimidine-2,4-diamine 
• 1374993-33-5 5-nitro-2-N-phenylpyrimidine-2,4-diamine 
• 1374993-34-6 2-N-benzyl-N₂-methyl-5-nitropyrimidine-2,4-diamine 

Relevant academic research and scientific papers

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.

Substituted pteridinones as p90 ribosomal S6 protein kinase (RSK) inhibitors: A structure-activity study

The activity of p90 ribosomal S6 kinase 2 (RSK2) has emerged as an attractive target for cancer therapy due to its role in the regulation of diverse cellular processes, such as cell transformation and proliferation. Several pan-RSK inhibitors have been identified with BI-D1870 and the pseudo-analogs LJH685 and LJI308 being the most selective, potent, and frequently used small molecule inhibitors. We designed and synthesized a series of pteridinones and pyrimidines to evaluate the structural features of BI-D1870 that are required for RSK2 inhibition. We have identified inhibitors of RSK2 activity, evaluated their target engagement in cells, and measured their effect on cell viability and cytotoxicity in the MOLM-13 acute myeloid leukemia (AML) cell line. The results of our studies support that RSK2 inhibition can be achieved in MOLM-13 cells without potent cytotoxicity. The structure-activity data from this study will be used as a platform to develop novel RSK2 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.

BTK INHIBITOR

Provided are a series of BTK inhibitors, and specifically disclosed are a compound, pharmaceutically acceptable salt thereof, tautomer thereof or prodrug thereof represented by formula (I), (II), (III) or (IV).

ARYLAMINO PURINE DERIVATIVES, PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF

Arylamino purine derivatives represented by formula I and their preparation method are disclosed, wherein each substituent is defined as in the description. The derivatives have an inhibitory effect on non-small cell lung cancer with deletion mutation of exon 19 or L858R point mutation of exon 21 in epidermal growth factor receptor (EGFR).

Structural optimization and structure-activity relationships of N 2-(4-(4-methylpiperazin-1-yl)phenyl)- N 8-phenyl-9 H -purine-2,8-diamine derivatives, a new class of reversible kinase inhibitors targeting both EGFR-activating and resistance mutations

This paper describe the structural optimization of a hit compound, N 2-(4-(4-methylpiperazin-1-yl)phenyl)-N8-phenyl-9H-purine- 2,8-diamine (1), which is a reversible kinase inhibitor targeting both EGFR-activating and drug-resistance (T790M) mutations but has poor binding affinity. Structure-activity relationship studies led to the identification of 9-cyclopentyl-N2-(4-(4-methylpiperazin-1-yl)phenyl)-N 8-phenyl-9H-purine-2,8-diamine (9e) that exhibits significant in vitro antitumor potency against the non-small-cell lung cancer (NSCLC) cell lines HCC827 and H1975, which harbor EGFR-activating and drug-resistance mutations, respectively. Compound 9e was further assessed for potency and selectivity in enzymatic assays and in vivo anti-NSCLC studies. The results indicated that compound 9e is a highly potent kinase inhibitor against both EGFR-activating and resistance mutations and has good kinase spectrum selectivity across the kinome. In vivo, oral administration of compound 9e at a dose of 5 mg/kg caused rapid and complete tumor regression in a HCC827 xenograft model, and an oral dose of 50 mg/kg initiated a considerable antitumor effect in an H1975 xenograft model.

Efficient synthesis of flupirtine analogues derived from pyrimidine

The synthesis of novel N2-substituted 5-alkoxycarbonylamino-2,4- diaminopyrimidines, 5-acylamino-2,4-diaminopyrimidines, and 2,4-diamino-5- ureidopyrimidines as analogues of the analgesic flupirtine is described. Copyright

8-OXODIHYDROPURINE DERIVATIVE

The present invention provides a compound represented by the formula (1) or a pharmaceutically acceptable salt thereof (wherein W represents a hydrogen atom, a halogen atom, or the others; A represents an alkyl group optionally substituted by aryl group or the others, an aryl group, or the others; and one of X and Y represents a di-substituted alkylaminocarbonyl group, or the others, and the other represents a hydrogen atom, an alkyl group, an alkylcarbonyl group, or the others); a medicament or a pharmaceutical composition for treatment or prophylaxis of FAAH-related diseases such as depression, anxiety disorder or pains, comprising the compound or the like as an active ingredient; a use of the compound or the like; and a method for treatment or prophylaxis using the compound or the like.