54605-72-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-1H-pyrazole-4-carbaldehyde is used as a synthetic intermediate for the preparation of phenyl-pyrazolyl acrylic acid benzylidene carbohydrazide derivatives. These derivatives exhibit antichagasic activities, making them valuable in the development of treatments for Chagas disease, a parasitic infection that affects millions of people worldwide.
Additionally, 1-Phenyl-1H-pyrazole-4-carbaldehyde is used as a precursor in the synthesis of ORL1 receptor antagonists. ORL1 receptors, also known as opioid receptor-like 1, are involved in pain perception and regulation. Antagonists of these receptors have potential applications in the development of novel pain management therapies, offering alternative treatment options for patients suffering from chronic pain conditions.

InChI:InChI=1/C10H8N2O/c13-8-9-6-11-12(7-9)10-4-2-1-3-5-10/h1-8H

Upstream product

• 35715-71-0 1-phenyl-4-pyrazolylmethyl chloride 
• 1126-00-7 1-phenylpyrazole 
• 68-12-2 N,N-dimethyl-formamide 
• 2600-63-7 3-(1-phenylpyrazol-4-yl)acrylaldehyde 
• 100-63-0 phenylhydrazine 
• 57023-37-7 3-[(E)-(2-phenylhydrazinylidene)methyl]pyridine 
• 27935-60-0 acetaldehyde-(Z)-phenylhydrazone 
• 497-19-8 sodium carbonate 
• 100-97-0 hexamethylenetetramine 
• 35344-95-7 1H-pyrazole-4-carbaldehyde 
• 71-43-2 benzene 
• 462-06-6 fluorobenzene 
• 591-50-4 iodobenzene 
• 885-94-9 ethyl 1-phenylpyrazole-4-carboxylate 

Downstream Products

• 2644-92-0 2-phenyl-4-(1-phenyl-1H-pyrazol-4-ylmethylene)-4H-oxazol-5-one 
• 100142-20-9 1-phenyl-4-propenyl-1H-pyrazole 
• 18833-00-6 1-(1-phenyl-1H-pyrazol-4-yl)-propan-1-one 
• 100722-37-0 1-(1-phenyl-1H-pyrazol-4-yl)-pentan-1-ol 
• 104216-04-8 1-(1-phenyl-1H-pyrazol-4-yl)-ethanol 
• 102241-74-7 1,3t-bis-(1-phenyl-1H-pyrazol-4-yl)-propenone 
• 100382-21-6 2-((1-phenyl-1H-pyrazol-4-yl)methylene)malonic acid 
• 27268-04-8 (E)-3-(1-phenylpyrazol-4-yl)prop-2-enoic acid 
• 100722-38-1 2,2-dimethyl-1-(1-phenyl-1H-pyrazol-4-yl)-propan-1-ol 
• 107417-06-1 2-methyl-1-(1-phenyl-1H-pyrazol-4-yl)-propan-1-ol 
• 107417-07-2 1-(1-phenyl-1H-pyrazol-4-yl)-butan-1-ol 
• 101350-45-2 phenyl-(1-phenyl-1H-pyrazol-4-yl)-methanol 
• 33183-64-1 1-phenyl-3-(1-phenyl-1H-pyrazol-4-yl)-propenone 
• 70817-26-4 (1-phenyl-1H-pyrazol-4-yl)methanol 

Relevant academic research and scientific papers

Anxiolytic- and antidepressant-like effects of new phenylpiperazine derivative LQFM005 and its hydroxylated metabolite in mice

The current treatments available for anxiety and depression are only palliative. Full remission has remained elusive, characterizing unmet medical needs. In the scope of an academic drug discovery program, we describe here the design, synthesis, in vitro metabolism prediction and pharmacological characterization of a new piperazine compound, 1-(4-methoxyphenyl)?4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazine (LQFM005), and of its main putative metabolite, 4-(4-((4-(4-methoxyphenyl)piperazin-1-yl)methyl)? 1H-pyrazol-1-yl)phenol (LQFM235). The production of the metabolite was initially performed by in vitro biotransformation of LQFM005 using Aspergillus candidus and then by chemical synthesis. Oral administration of either 12 or 24 μmol/kg LQFM005 to mice did not affect spontaneous locomotor activity but increased the time spent in the center of the open field. Both LQFM005 and LQFM235 (24 μmol/kg) increased the time spent by the mice in the open arms of the elevated plus maze (EPM), a good indication of anxiolytic-like effect, and decreased the immobility time in the forced swimming test (FST), suggesting an antidepressant-like effect. The previous administration of WAY-100635 (a 5-HT1A antagonist) abolished the effects of LQFM005 in both EPM and FST. Binding experiments showed that LQFM005 and its metabolite bind to the 5-HT1A receptor with a moderate affinity (Ki around 5–9 μM). The two compounds are relatively safe, as indicated by cytotoxic assessment using the 3T3 fibroblast cell line and estimated LD50 around 600 mg/kg. In conclusion, oral administration of the newly synthesized phenylpiperazines produced anxiolytic- and antidepressant-like effects in behavioral tests, putatively in part through the activation of 5-HT1A receptors.

NOVEL COMPOUND AS MTOR INHIBITOR AND USE THEREOF

The present invention relates to a novel compound as an mTOR inhibitor and a use thereof and, more specifically, to a novel compound represented by formula 1 that exhibits mTOR inhibitory activity and a pharmaceutical composition comprising same as an act

Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants

We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.

Electrophotocatalytic SNAr Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base

The electrophotocatalytic SNAr reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.

Design, synthesis and pharmacological assessment of new pyrazole compounds

Aims: This study investigated the antinociceptive and anti-inflammatory effects of new pyrazole compounds LQFM011(5), LQFM043(6) and LQFM044(7) as well as the mechanisms of action and acute in vitro toxicity. Main methods: The antinociceptive activity was evaluated using the acetic acid-induced abdominal writhing test, formalin-induced pain test and the Randall–Selitto test. The anti-inflammatory activity was evaluated using models of paw oedema and pleurisy induced by carrageenan; cell migration, the levels of tumour necrosis factor α (TNF-α) and myeloperoxidase (MPO) enzyme activity were evaluated. In addition, the ability to inhibit phospholipase A2 (PLA2) in vitro and docking in PLA2 were used. Acute oral systemic toxicity in mice was evaluated through the neutral red uptake assay. Key findings: The synthesised compounds (5–7), delivered via gavage (p.o.) at 70, 140 or 280 μmol/kg, decreased the number of writhings induced by acetic acid; the three compounds (280 μmol/kg p.o.) reduced the paw licking time in the first and second phase of the formalin test and decreased the nociceptive threshold variation in the Randall–Selitto test. Furthermore, this dose reduced oedema formation, leucocyte migration (specifically through reduction in polymorphonuclear cell movement) and increased mononuclear cells. MPO activity and the levels of pro-inflammatory cytokines TNF-α were decreased. Evaluation of PLA2 inhibition via the docking simulation revealed more interactions of LQFM043R(6) and LQFM044(7), data that corroborated the half-maximal inhibitory concentration (IC50) of PLA2 inhibition in vitro. Therefore, LQFM011(5), LQFM043(6) and LQFM044(7) were classified with the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) as category 4.

Anti-inflammatory and antinociceptive activity profile of a new lead compound – LQFM219

LQFM219 is a molecule designed from celecoxibe (COX-2 inhibitor) and darbufelone (inhibitor of COX-2 and 5-LOX) lead compounds through a molecular hybridisation strategy. Therefore, this work aimed to investigate the antinociceptive and anti-inflammatory activities of this new hybrid compound. The acute oral systemic toxicity of LQFM219 was evaluated via the neutral red uptake assay. Acetic acid-induced abdominal writhing and CFA-induced mechanical hyperalgesia were performed to evaluate the antinociceptive activity, and the anti-oedematogenic activity was studied by CFA-induced paw oedema and croton oil-induced ear oedema. Moreover, the acute anti-inflammatory activity was determined by carrageenan-induced pleurisy. In addition, cell migration, myeloperoxidase enzyme activity, and TNF-α and IL-1β levels were determined in pleural exudate. Moreover, a redox assay was conducted using electroanalytical and DPPH methods. The results demonstrated that LQFM219 was classified as GHS category 4, and it showed better free radical scavenger activity compared to BHT. Besides, LQFM219 decreased the number of writhings induced by acetic acid and the response to the mechanical stimulus in the CFA-induced mechanical hyperalgesia test. Furthermore, LQFM219 reduced oedema formation, cell migration, and IL-1β and TNF-α levels in the pleural cavity and inhibited myeloperoxidase enzyme activity. Thus, our study provides that the new pyrazole derivative, LQFM219, demonstrated low toxicity, antinociceptive and anti-inflammatory potential in vitro and in vivo.

Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication

Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.

Novel choline analog 2-(4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethan-1-ol produces sympathoinhibition, hypotension, and antihypertensive effects

The search for new drugs remains an important focus for the safe and effective treatment of cardiovascular diseases. Previous evidence has shown that choline analogs can offer therapeutic benefit for cardiovascular complications. The current study investigates the effects of 2-(4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazin-1-yl)ethan-1-ol (LQFM032) on cardiovascular function and cholinergic-nitric oxide signaling. Synthesized LQFM032 (0.3, 0.6, or 1.2?mg/kg) was administered by intravenous and intracerebroventricular routes to evaluate the potential alteration of mean arterial pressure, heart rate, and renal sympathetic nerve activity of normotensive and hypertensive rats. Vascular function was further evaluated in isolated vessels, while pharmacological antagonists and computational studies of nitric oxide synthase and muscarinic receptors were performed to assess possible mechanisms of LQFM032 activity. The intravenous and intracerebroventricular administration of LQFM032 elicited a temporal reduction in mean arterial pressure, heart rate, and renal sympathetic nerve activity of rats. The cumulative addition of LQFM032 to isolated endothelium-intact aortic rings reduced vascular tension and elicited a concentration-dependent relaxation. Intravenous pretreatment with L-NAME (nitric oxide synthase inhibitor), atropine (nonselective muscarinic receptor antagonist), pirenzepine, and 4-DAMP (muscarinic M1 and M3 subtype receptor antagonist, respectively) attenuated the cardiovascular effects of LQFM032. These changes may be due to a direct regulation of muscarinic signaling as docking data shows an interaction of choline analog with M1 and M3 but not nitric oxide synthase. Together, these findings demonstrate sympathoinhibitory, hypotensive, and antihypertensive effects of LQFM032 and suggest the involvement of muscarinic receptors.

Pyridazinone compounds and use thereof (by machine translation)

The invention discloses a pyridazinone compounds, structure such as formula I shown: In the type of each substituent is as defined in the specification. The compounds of this invention have broad-spectrum antibacterial, insecticidal or acaricidal activity, the cucumber downy mildew, wheat powdery mildew, corn rust, rice blast, cucumber anthracnose and has excellent control effect. (by machine translation)

Anti-inflammatory effect of a new piperazine derivative: (4-methylpiperazin-1-yl)(1-phenyl-1H-pyrazol-4-yl)methanone

Aims: This study investigates the anti-nociceptive and anti-inflammatory effects of new piperazine compound (LQFM182) as well as the toxicity acute in vitro. Main methods: To evaluate the anti-nociceptive activity, the acetic acid-induced abdominal writhing test, tail flick test and formalin-induced pain test were used. The anti-inflammatory activity was evaluated using the models of paw oedema and pleurisy induced by carrageenan and some inflammatory parameters were evaluated, including cell migration, myeloperoxidase enzyme activity and the levels of TNF-α and IL-1β cytokines in pleural exudate. The acute oral systemic toxicity of LQFM182 in mice was evaluated through the neutral red uptake (nru) assay. Key findings: LQFM182 (50, 100 or 200?mg/kg, p.o.) decreased the number of writhings induced by acetic acid in a dose-dependent manner, and an intermediate dose (100?mg/kg, p.o.) reduced the paw licking time of animals in the second phase of the formalin test. Furthermore, LQFM182 (100?mg/kg, p.o.) reduced oedema formation at all hours of the paw oedema induced by carrageenan test and in pleurisy test reduced cell migration from the reduction of polymorphonuclear cells, myeloperoxidase enzyme activity and the levels of pro-inflammatory cytokines IL-1β and TNF-α. Therefore, it was classified in GHS category 300?50??2000?mg/kg. Significance: Reduction of the TNF-α and IL-1β levels.