51516-68-8

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& is utilized as a key building block in the synthesis of various pharmaceuticals due to its unique chemical structure and properties. Its role in the development of new drugs is crucial, particularly in the context of its potential antitumor and anticancer activities.
Used in Organic Synthesis:
As a pyrazole derivative, 5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& is employed as an intermediate in organic synthesis, contributing to the creation of a wide array of chemical compounds with diverse applications.
Used in Medicinal Chemistry:
5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& is leveraged in medicinal chemistry for its potential therapeutic effects. Its exploration in antitumor and anticancer research underscores its importance in the quest for novel treatments in oncology.
Used in Research and Development:
5-AMINO-1-(3-CHLOROPHENYL)-1H-PYRAZOLE-& is a subject of ongoing research and development efforts, aimed at uncovering its full potential in the pharmaceutical sector. This includes investigations into its mechanisms of action, efficacy, and safety profiles, all critical for its eventual application in clinical settings.

InChI:InChI=1/C10H7ClN4/c11-8-3-1-2-4-9(8)15-10(13)7(5-12)6-14-15/h1-4,6H,13H2

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 14763-20-3 3-chlorophenyl hydrazine 
• 109-77-3 malononitrile 
• 123-06-8 Ethoxymethylenemalononitrile 
• 2312-23-4 m-chlorophenylhydrazine hydrochloride 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 135108-52-0 4-Amino-1-(3-chloro-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 135108-72-4 4-Amino-1-(3-chloro-phenyl)-5-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 138548-43-3 1-Benzoyl-3-[2-(3-chloro-phenyl)-4-cyano-2H-pyrazol-3-yl]-urea 
• 135108-73-5 4-Amino-1-(3-chloro-phenyl)-5-propyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 58791-87-0 1-(3-chloro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine 
• 1094618-86-6 1-(3-chlorophenyl)-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b]quinolin-4-amine 
• 1094618-90-2 1-(3-chlorophenyl)-1,5,6,7-tetrahydrocyclopenta[e]pyrazolo[3,4-b]pyridin-4-amine 
• 1269662-45-4 ethyl 4-amino-1-(3-chlorophenyl)-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1269662-38-5 methyl 4-amino-1-(3-chlorophenyl)-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 1431459-14-1 5-[1-(3-chlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 1452871-34-9 C₁₃H₁₀ClN₅O 
• 1452871-37-2 C₁₄H₁₂ClN₅O 
• 1613037-28-7 5-[5-amino-1-(3′-chlorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 50427-78-6 5-amino-1-(3-chlorophenyl)-1H-pyrazole-4-carboxamide 

Relevant academic research and scientific papers

Synthesis of pyrazole-carboxamides and pyrazole-carboxylic acids derivatives: Simple methods to access powerful building blocks

Hybrid systems containing pyrazole moiety show a wide spectrum of biological activities. To access novel hybrids with pyrazole ring, in this work we synthesized twenty pyrazole-carboxylic acids and twenty pyrazole-carboxamides, using simple synthetic methods, to be used as building blocks in the development of new structures.

A Convenient Synthesis of Pyrazole-imidazoline Derivatives by Microwave Irradiation

A series of 28 hybrids pyrazole-imidazolines 1a–n and 2a–n were synthesized by a new methodology using microwave irradiation, in short time (20–30?min), in low power (50–70?W), and in 34–92% yield. Among all methodologies evaluated, no side products were obtained. All derivatives were completely characterized by FT–IR, 1H and 13C NMR, GC–MS, and HRMS.

Synthesis, structure-activity relationship and trypanocidal activity of pyrazole-imidazoline and new pyrazole-tetrahydropyrimidine hybrids as promising chemotherapeutic agents for Chagas disease

Drug therapy for Chagas disease remains a major challenge as potential candidate drugs have failed clinical trials. Currently available drugs have limited efficacy and induce serious side effects. Thus, the discovery of new drugs is urgently needed in the fight against Chagas' disease. Here, we synthesized and evaluated the biological effect of pyrazole-imidazoline (1a-i) and pyrazole-tetrahydropyrimidine (2a-i) derivatives against relevant clinical forms of Trypanosoma cruzi. The structure-activity relationship (SAR), drug-target search, physicochemical and ADMET properties of the major active compounds in vitro were also assessed in silico. Pyrazole derivatives showed no toxicity in Vero cells and also no cardiotoxicity. Phenotypic screening revealed two dichlorinated pyrazole-imidazoline derivatives (1c and 1d) with trypanocidal activity higher than that of benznidazole (Bz) against trypomastigotes; these were also the most potent compounds against intracellular amastigotes. Replacement of imidazoline with tetrahydropyrimidine in the pyrazole compounds completely abolished the trypanocidal activity of series 2(a-i) derivatives. The physicochemical and ADMET properties of the compounds predicted good permeability, good oral bioavailability, no toxicity and mutagenicity of 1c and 1d. Pyrazole nucleus had high frequency hits for cruzipain in drug-target search and structure activity relationship (SAR) analysis of pyrazole-imidazoline derivatives revealed enhanced activity when chlorine atom was inserted in meta-positions of the benzene ring. Additionally, we found evidence that both compounds (1c and 1d) have the potential to interact non-covalently with the active site of cruzipain and also inhibit the cysteine proteinase activity of T. cruzi. Collectively, the data presented here reveal pyrazole derivatives with promise for further optimization in the therapy of Chagas disease.

Synthesis, in vitro and in vivo anticancer activity of novel 1-(4-imino-1-substituted-1H-pyrazolo[3,4-d]pyrimidin-5(4H)-yl)urea derivatives

A series of pyrazolo[3,4-d]pyrimidine and urea hybrids have been designed, synthesized and evaluated for their anticancer activity in vitro and in vivo cancer models. Among them, compounds 28, 30, 33, 36 and 37 showed promising cytotoxicity against tested cancer cell lines. Compound 37 (CBS-1) appeared as the most active derivative and it exhibited better cytotoxicity against all tested cell lines as compared to doxorubicin. CBS-1 successfully inhibited cell cycle progression and displayed good apoptosis in A549 cells. CBS-1 significantly induced caspase-3 activation and suppressed NF-κB and IL-6 activation in immunocytochemistry, qPCR and western blot analysis. Additionally, CBS-1 prominently displayed tumoricidal effects in lung adenocarcinoma in vivo xenograft nude mice model.

Effectiveness of novel 5-(5-amino-1-aryl-1H-pyrazol-4-yl)-1H-tetrazole derivatives against promastigotes and amastigotes of leishmania amazonensis

In this research, a series of substituted 5-(5-amino-1-aryl-1H-pyrazol-4- yl)-1H-tetrazoles were synthesized and evaluated for in vitro antileishmanial activity. Among the derivatives, examined compounds 3b and 3l exhibited promising activity against promastigotes and amastigotes forms of Leishmania amazonensis. The cytotoxicity of these compounds was evaluated on murine cells, giving access to the corresponding selectivity index (SI).

An efficient synthesis of new 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3 + 2] cycloaddition reaction

A series of new 5-(1-aryl-1H-pyrazole-4-yl)-1H-tetrazoles 4a-l were synthesized via [3 + 2] cycloaddition reaction from 1-aryl-1H-pyrazole-4- carbonitriles 3a-l, sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64-85%. The structures of these newly synthesized compounds were determined from the IR, 1H- and 13C-NMR spectroscopic data and elemental analyses.

Synthesis and antileishmanial evaluation of 1-aryl-4-(4,5-dihydro-1H- imidazol-2-yl)-1H-pyrazole derivatives

A series of 1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazoles (4a-g) and 5-amino-1-aryl-4-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazoles (5a-g) were synthesized and evaluated in vitro against three Leishmania species: L. amazonensis, L. braziliensis and L. infantum (L. chagasi syn.). The cytotoxicity was assessed. Among the derivatives examined, six compounds emerged as the most active on promastigotes forms of L. amazonensis with IC50 values ranging from 15 to 60 μM. The reference drug pentamidine presented IC 50 = 10 μM. However, these new compounds were less cytotoxic than pentamidine. Based on these results, the more promising derivative 5d was tested further in vivo. This compound showed inhibition of the progression of cutaneous lesions in CBA mice infected with L. amazonensis relative to an untreated control.

Mnk1 or Mnk2 inhibitors

The present invention relates to novel pharmaceutical compositions comprising pyrazolopyrimidine compounds. Moreover, the present invention relates to the use of the pyrazolopyrimidine compounds of the invention for the production of pharmaceutical compos

Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine

Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.