133261-06-0

Basic information

• Product Name: ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE
• Synonyms: ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE;ethyl 3-cyclopropyl-1H-pyrazole-5-carboxylate;Ethyl 5-cyclopropyl-2H-pyrazole-3-carboxylate;5-Cyclopropyl-1H-pyrazole-3-carboxylic acid ethyl ester;5-cyclopropyl-1H-Pyrazole-3-Carbocylic acid ethyl ester
• CAS NO: 133261-06-0
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.2
• Mol File: 133261-06-0.mol

Chemical Properties

• Melting Point: 90-92 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 352.0±30.0 °C(Predicted)
• Appearance: /
• Density: 1.256±0.06 g/cm3(Predicted)
• PKA: 11.60±0.10(Predicted)
• CAS DataBase Reference: ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE(133261-06-0)
• EPA Substance Registry System: ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE(133261-06-0)

Safety Data

• Hazardous Substances Data: 133261-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE is used as an intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and organic molecules. Its unique structure and reactivity make it a valuable building block in the creation of diverse medicinal agents.
Used in Organic Synthesis:
In the field of organic synthesis, ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE serves as a key component in the synthesis of a wide range of organic compounds. Its versatility and reactivity enable the formation of various complex molecules, expanding the scope of chemical research and applications.
Used in Chemical Research:
ETHYL 5-CYCLOPROPYL-1H-PYRAZOLE-3-CARBOXYLATE is utilized in chemical research to explore its properties, reactivity, and potential applications. Its unique structure allows researchers to investigate new reaction pathways and develop innovative synthetic methods, further advancing the field of chemistry.

Upstream product

• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 765-43-5 Cyclopropyl methyl ketone 
• 95-92-1 oxalic acid diethyl ester 
• 184297-33-4 C₉H₁₄O₃ 
• 21080-80-8 ethyl 4-cyclopropyl-2,4-dioxobutanoate 

Downstream Products

• 890591-72-7 5-cyclopropyl-1H-pyrazole-3-carboxylic acid 
• 1232136-97-8 3-(N-methylaminomethyl)-5-cyclopropyl-1H-pyrazole 
• 926300-29-0 (E)-3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}-N-(pentylsulfonyl)propenamide 
• 926296-48-2 (E)-3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}propenoic acid 
• 926296-45-9 ethyl (E)-3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}propenoate 
• 926296-43-7 {1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}methanol 
• 926300-30-3 3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}-N-(pentylsulfonyl)propanamide 
• 926296-47-1 3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-propyl-1H-pyrazol-5-yl}propanoic acid 
• 926296-46-0 3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}propanoic acid 
• 1357002-33-5 ethyl 3-{1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazol-5-yl}propanoate 
• 926296-42-6 ethyl 1-[2-chloro-4-(trifluoromethyl)benzyl]-3-cyclopropyl-1H-pyrazole-5-carboxylate 

Relevant articles and documents

From a Designer Drug to the Discovery of Selective Cannabinoid Type 2 Receptor Agonists with Favorable Pharmacokinetic Profiles for the Treatment of Systemic Sclerosis

Synthetic cannabinoids, as exemplified by SDB-001 (1), bind to both CB1 and CB2 receptors and exert cannabimimetic effects similar to (-)-trans-Δ9-tetrahydrocannabinol, the main psychoactive component present in the cannabis plant. As CB1 receptor ligands were found to have severe adverse psychiatric effects, increased attention was turned to exploiting the potential therapeutic value of the CB2 receptor. In our efforts to discover novel and selective CB2 receptor agonists, 1 was selected as a starting point for hit molecule identification and a class of 1H-pyrazole-3-carboxamide derivatives were thus designed, synthesized, and biologically evaluated. Systematic structure-activity relationship investigations resulted in the identification of the most promising compound 66 as a selective CB2 receptor agonist with favorable pharmacokinetic profiles. Especially, 66 treatment significantly attenuated dermal inflammation and fibrosis in a bleomycin-induced mouse model of systemic sclerosis, supporting that CB2 receptor agonists might serve as potential therapeutics for treating systemic sclerosis.

Cascade regioselective synthesis of pyrazoles from nitroallylic acetates and N-tosyl hydrazine

A simple, practical, and regioselective synthetic protocol for the formation of pyrazoles was developed. Unlike all other previously reported reactions of nitroallylic acetates, this process was initiated by a S N2 reaction at the electrophilic γ site. A plausible mechanism for the cascade SN2-Michael synthesis is proposed.

A new class of non-thiazolidinedione, non-carboxylic-acid-based highly selective peroxisome proliferator-activated receptor (PPAR) γ agonists: Design and synthesis of benzylpyrazole acylsulfonamides

Herein, we describe the design, synthesis, and structure-activity relationships of novel benzylpyrazole acylsulfonamides as non-thiazolidinedione (TZD), non-carboxylic-acid-based peroxisome proliferator-activated receptor (PPAR) γ agonists. Docking model analysis of in-house weak agonist 2 bound to the reported PPARγ ligand binding domain suggested that modification of the carboxylic acid of 2 would help strengthen the interaction of 2 with the TZD pocket and afford non-carboxylic-acid-based agonists. In this study, we used an acylsulfonamide group as the ring-opening analog of TZD as an isosteric replacement of carboxylic acid moiety of 2; further, preliminary modification of the terminal alkyl chain on the sulfonyl group gave the lead compound 3c. Subsequent optimization of the resulting compound gave the potent agonists 25c, 30b, and 30c with high metabolic stability and significant antidiabetic activity. Further, we have described the difference in binding mode of the carboxylic-acid-based agonist 1 and acylsulfonamide 3d.

Synthesis of 3-aminomethyl-substituted pyrazoles and isoxazoles

A series of new 3-(aminomethyl)pyrazoles and 3-(aminomethyl)isoxazoles was synthesized along a route involving the formation as key intermediates of esters of 5-substituted 1H-pyrazole-3-carboxylic and 1H-isoxazole-3-carboxylic acids. All compounds obtain

Agonist lead identification for the high affinity niacin receptor GPR109a

A strategy for lead identification of new agonists of GPR109a, starting from known compounds shown to activate the receptor, is described. Early compound triage led to the formulation of a binding hypothesis and eventually to our focus on a series of pyrazole acid derivatives. Further elaboration of these compounds provided a series of 5,5-fused pyrazoles to be used as lead compounds for further optimization.

Fluorinated pyrazole acids are agonists of the high affinity niacin receptor GPR109a

A series of 5-alkyl pyrazole-3-carboxylic acids were prepared and found to act as potent and selective agonists of the human GPCR, GPR109a, the high affinity nicotinic acid receptor. No activity was observed at the highly homologous low affinity niacin receptor, GPR109b. A further series of 4-fluoro-5-alkyl pyrazole-3-carboxylic acids were shown to display similar potency. One example from the series was shown to have improved properties in vivo compared to niacin.

THERAPEUTIC AGENT FOR DIABETES

The present invention provides an agent for the prophylaxis or treatment of diabetes, which is associated with a ferwer side effects such as body weight gain, adipocyte accumulation, cardiac hypertrophy and the like, and which contains a compound represented by the formula: wherein each symbol is as defined in the specification, or a salt thereof or a prodrug thereof.