309740-49-6

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 1-Methyl-4-nitro-1H-pyrazole-5-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, Methyl 1-Methyl-4-nitro-1H-pyrazole-5-carboxylate is used as a precursor in the production of pesticides and other agrochemicals. Its incorporation aids in the creation of effective compounds for pest and disease control in agriculture.
Used as an Antifungal Agent:
Methyl 1-Methyl-4-nitro-1H-pyrazole-5-carboxylate is utilized as an antifungal agent due to its potential biological activities. It can be employed in the development of treatments for fungal infections, offering a new avenue for combating resistant strains.
Used as an Antibacterial Agent:
Similarly, Methyl 1-Methyl-4-nitro-1H-pyrazole-5-carboxylate is also used as an antibacterial agent, indicating its broad-spectrum activity against bacteria. It can contribute to the development of new antibiotics to address the growing issue of antibiotic resistance.
Used in Material Science:
Methyl 1-Methyl-4-nitro-1H-pyrazole-5-carboxylate has potential applications in the field of material science. Its unique chemical properties can be harnessed to produce functional materials with specific characteristics for various industrial applications.
Used in Drug Discovery:
In the realm of drug discovery, Methyl 1-Methyl-4-nitro-1H-pyrazole-5-carboxylate serves as a valuable compound for the exploration of new therapeutic agents. Its presence in the synthesis process can lead to the identification of novel drug candidates with improved efficacy and safety profiles.

Upstream product

• 138786-86-4 methyl 4-nitro-1H-pyrazole-3-carboxylate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 138786-86-4 4-nitro-2H-pyrazole-3-carboxylic acid methyl ester 
• 77-78-1 dimethyl sulfate 
• 5334-40-7 4-nitro-1H-pyrazole-5-carboxylic acid 
• 3185-99-7 Methyl p-tolyl sulfone 
• 92534-69-5 1-methyl-4-nitro-1H-pyrazole-5-carboxylic acid 

Downstream Products

• 92534-72-0 1-methyl-4-nitro-1H-pyrazole-5-carboxamide 
• 83824-38-8 1-methyl-1H-pyrazolo[4,3-d]pyrimidine-5,7-(4H,6H)-dione 
• 939979-32-5 5,7-dichloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine 
• 83824-38-8 1-methylpyrazolo[4,3-d]pyrimidine-5,7-diol 
• 92534-73-1 4-amino-1-methyl-1H-pyrazole-5-carboxamide 
• 1021497-91-5 4-[2-(4-bromo-phenylsulfanyl)-acetylamino]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Methylation of 4-nitro-3(5)-pyrazolecarboxylic acid

Reactions of 4-nitro-3(5)-pyrazolecarboxylic acid dipotassium salt with different methylating agents in various solvents have been investigated to improve the synthesis of isomeric 1-methyl-4-nitro-3- and -5-pyrazolecarboxylic acids.

Novel pyrazolo[4,3-d]pyrimidine microtubule targeting agents (MTAs): Synthesis, structure–activity relationship, in vitro and in vivo evaluation as antitumor agents

The design, synthesis, and biological evaluation of a series novel N1?methyl pyrazolo[4,3-d]pyrimidines as inhibitors of tubulin polymerization and colchicine binding were described here. Synthesis of target compounds involved alkylation of the pyrazolo scaffold, which afforded two regioisomers. These were separated, characterized and identified with 1H NMR and NOESY spectroscopy. All compounds, except 10, inhibited [3H]colchicine binding to tubulin, and the potent inhibition was similar to that obtained with CA-4. Compounds 9 and 11–13 strongly inhibited the polymerization of tubulin, with IC50 values of 0.45, 0.42, 0.49 and 0.42 μM, respectively. Compounds 14–16 inhibited the polymerization of tubulin with IC50s near ～1 μM. Compounds 9, 12, 13 and 16 inhibited MCF-7 breast cancer cell lines and circumvented βIII-tubulin mediated cancer cell resistance to taxanes and other MTAs, and compounds 9–17 circumvented Pgp-mediated drug resistance. In the standard NCI testing protocol, compound 9 exhibited excellent potency with low to sub nanomolar GI50 values (≤10 nM) against most tumor cell lines, including several multidrug resistant phenotypes. Compound 9 was significantly (P 0.0001) better than paclitaxel at reducing MCF-7 TUBB3 (βIII-tubulin overexpressing) tumors in a mouse xenograft model. Collectively, these studies support the further preclinical development of the pyrazolo[4,3-d]pyrimidine scaffold as a new generation of tubulin inhibitors and 9 as an anticancer agent with advantages over paclitaxel.

Design, Synthesis, and Physicochemical and Pharmacological Profiling of 7-Hydroxy-5-oxopyrazolo[4,3-b]pyridine-6-carboxamide Derivatives with Antiosteoarthritic Activity in Vivo

The hallmark of joint diseases, such as osteoarthritis (OA), is pain, originating from both inflammatory and neuropathic components, and compounds able to modulate the signal transduction pathways of the cannabinoid type-2 receptor (CB2R) can represent a helpful option in the treatment of OA. In this perspective, a set of 18 cannabinoid type-2 receptor (CB2R) ligands was developed based on an unprecedented structure. With the aim of improving the physicochemical properties of previously reported 4-hydroxy-2-quinolone-3-carboxamides, a structural optimization program led to the discovery of isosteric 7-hydroxy-5-oxopyrazolo[4,3-b]pyridine-6-carboxamide derivatives. These new compounds are endowed with high affinity for the CB2R and moderate to good selectivity over the cannabinoid type-1 receptor (CB1R), associated with good physicochemical characteristics. As to the functional activity at the CB2R, compounds able to act either as agonists or as inverse agonists/antagonists were discovered. Among them, compound 51 emerged as a potent CB2R agonist able to reduce pain in rats carrying OA induced by injection of monoiodoacetic acid (MIA).

Discovery of novel serine palmitoyltransferase inhibitors as cancer therapeutic agents

We pursued serine palmitoyltransferase (SPT) inhibitors as novel cancer therapeutic agents based on a correlation between SPT inhibition and growth suppression of cancer cells. High-throughput screening and medicinal chemistry efforts led to the identification of structurally diverse SPT inhibitors 4 and 5. Both compounds potently inhibited SPT enzyme and decreased intracellular ceramide content. In addition, they suppressed cell growth of human lung adenocarcinoma HCC4006 and acute promyelocytic leukemia PL-21, and displayed good pharmacokinetic profiles. Reduction of 3-ketodihydrosphingosine, the direct downstream product of SPT, was confirmed under in vivo settings after oral administration of compounds 4 and 5. Their anti-tumor efficacy was observed in a PL-21 xenograft mouse model. These results suggested that SPT inhibitors might have potential to be effective cancer therapeutics.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Pyrazolo[4,3-d]pyrimidines as Antitumor Agents

A compound of Formula I, or optionally a salt or a hydrate of the compound of Formula I is provided: wherein X is one selected from the group consisting of wherein R is an alkyl group having from one to six carbon atoms, and wherein R2 is a halogen atom. A pharmaceutical composition comprising a compound of Formula I, or optionally a salt or a hydrate of the compound of Formula I, and a pharmaceutically acceptable carrier, is provided. A method of treating a patient with cancer is set forth including administering a therapeutically acceptable amount of the compound of Formula I, or a salt or a hydrate of the compound of Formula I, or a pharmaceutical composition comprising a compound of Formula I.

HETEROCYCLIC COMPOUND

The present invention relates to a compound which can be useful for the treatment or prevention of SPT-related diseases including cancer and congenital diseases associated with sphingolipid accumulation (including Niemann-Pick disease).

HETEROAROMATIC DERIVATIVES AS NIK INHIBITORS

The present invention relates to pharmaceutical agents useful for therapy and/or prophylaxis in a mammal, and in particular to inhibitors of NF-κB-inducing kinase (NIK - also known as MAP3K14) useful for treating diseases such as cancer, inflammatory disorders, metabolic disorders and autoimmune disorders. The invention is also directed to pharmaceutical compositions comprising such compounds, and to the use of such compounds or pharmaceutical compositions for the prevention or treatment of diseases such as cancer, inflammatory disorders, metabolic disorders including obesity and diabetes, and autoimmune disorders.

Tankyrase inhibitor

The invention belongs to the technical field of medicines and particularly relates to a tankyrase inhibitor represented by a general formula (I) shown in the description and pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof, wherein R1, R2, R3, m, n, Z, L, Q, A, X1, X2 and Y are as defined in the description. The invention further relates to a preparation method for the compounds, pharmaceutical preparations and pharmaceutical compositions containing the compounds and application of the compound and the pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof in preparation of drugs for treating and/or preventing tankyrase mediated cancers and related diseases.

NITROGEN CONTAINING HETEROARYL COMPOUNDS

The invention is concerned with novel nitrogen-containing heteroaryl compounds of formula (I) wherein A1, A2, (a), R1, R2, R3, R4, R5 and R6 are as defined in the desc