5932-31-0

Usage

Uses

Used in Pharmaceutical Research and Development:
3-Cyclopentapyrazolecarboxylic acid, 1,4,5,6-tetrahydro-, ethyl ester is used as a building block for the synthesis of various bioactive molecules. Its unique chemical structure allows it to be a key intermediate in the preparation of drug candidates with potential for clinical use.
Used in Drug Development for Neurological Disorders:
In the pharmaceutical industry, 3-Cyclopentapyrazolecarboxylic acid, 1,4,5,6-tetrahydro-, ethyl ester is used as a starting material for the development of drugs targeting neurological disorders. Its unique structure and properties make it a promising candidate for the synthesis of molecules with potential therapeutic effects on neurological conditions.
Used in Drug Development for Cancer Treatment:
3-Cyclopentapyrazolecarboxylic acid, 1,4,5,6-tetrahydro-, ethyl ester is utilized in the development of anticancer drugs. Its unique chemical properties enable the synthesis of molecules with potential antitumor activity, making it a valuable compound in the search for novel cancer therapies.
Used in Drug Development for Infectious Diseases:
In the field of infectious diseases, 3-Cyclopentapyrazolecarboxylic acid, 1,4,5,6-tetrahydro-, ethyl ester is employed as a key intermediate in the synthesis of molecules with potential antimicrobial and antiviral properties. Its unique structure and properties contribute to the development of new drugs to combat various infectious diseases.

Upstream product

• 39163-39-8 oxo-(2-oxo-cyclopentyl)-acetic acid ethyl ester 
• 33537-18-7 cyclopentyl-oxo-acetic acid ethyl ester 
• 120-92-3 cyclopentanone 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 5932-32-1 1,4,5,6-tetrahydro-cyclopenta[c]pyrazole-3-carboxylic acid 
• 1201633-68-2 1,4,5,6-tetrahydrocyclopentapyrazole-3-(N-methyl)carboxamide 
• 1201769-40-5 3-(N-methylaminomethyl)-1,4,5,6-tetrahydrocyclopentapyrazole dihydrochloride 
• 1477483-21-8 C₁₆H₁₉N₅O 

Relevant academic research and scientific papers

Development of a scaleable synthesis of a partial nicotinic acid receptor agonist

A practical and efficient synthesis of 1,4,5,6-tetrahydro-3-(1Htetrazol- 5-yl)cyclopenta[c]pyrazole, 1, is described. A new one-pot process has been developed, starting from the commercially available 1H-tetrazole-5-carboxylic acid-ethyl ester sodium salt which is reacted in a pseudo-Claisen condensation reaction with cyclopentanone, followed by the addition of hydrazine.

Synthesis, Structure-Activity Relationship, and Pharmacophore Modeling Studies of Pyrazole-3-Carbohydrazone Derivatives as Dipeptidyl Peptidase IV Inhibitors

Type 2 diabetes mellitus (T2DM) is a metabolic disease and a major challenge to healthcare systems around the world. Dipeptidyl peptidase IV (DPP-4), a serine protease, has been rapidly emerging as an effective therapeutic target for the treatment for T2DM. In this study, a series of novel DPP-4 inhibitors, featuring the pyrazole-3-carbohydrazone scaffold, have been discovered using an integrated approach of structure-based virtual screening, chemical synthesis, and bioassay. Virtual screening of SPECS Database, followed by enzymatic activity assay, resulted in five micromolar or low-to-mid-micromolar inhibitory level compounds (1-5) with different scaffold. Compound 1 was selected for the further structure modifications in considering inhibitory activity, structural variability, and synthetic accessibility. Seventeen new compounds were synthesized and tested with biological assays. Nine compounds (6e, 6g, 6k-l, and 7a-e) were found to show inhibitory effects against DPP-4. Molecular docking models give rational explanation about structure-activity relationships. Based on eight DPP-4 inhibitors (1-5, 6e, 6k, and 7d), the best pharmacophore model hypo1 was obtained, consisting of one hydrogen bond donor (HBD), one hydrogen bond acceptor (HBA), and two hydrophobic (HY) features. Both docking models and pharmacophore mapping results are in agreement with pharmacological results. The present studies give some guiding information for further structural optimization and are helpful for future DPP-4 inhibitors design.

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

3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro-cyclopentapyrazole (MK-0354): A partial agonist of the nicotinic acid receptor, G-protein coupled receptor 109a, with antilipolytic but no vasodilatory activity in mice

The discovery and profiling of 3-(1H-tetrazol-5-yl)-1,4,5,6-tetrahydro- cyclopentapyrazole (5a, MK-0354), a partial agonist of GPR109a, is described. Compound 5a retained the plasma free fatty acid lowering effects in mice associated with GPR109a agonism,

METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS

A method of treating atherosclerosis, dyslipidemia and related conditions is disclosed wherein a compound of formula I: or a pharmaceutically acceptable salt or solvate thereof is administered to the patient in combination with a DP receptor antagonist. T

COMPOSITIONS FOR TREATING FLUSHING AND LIPID-ASSOCIATED DISORDERS COMPRISING NIACIN RECEPTOR PARTIAL AGONISTS

The invention provides a method of reducing flushing induced by niacin or a niacin analog in a subject, comprising administering to said subject an effective flush reducing amount of a niacin receptor partial agonist. In addition, the invention provides a

TETRAZOLE DERIVATIVES AND METHODS OF TREATMENT OF METABOLIC-RELATED DISORDERS THEREOF

The present invention relates to certain tetrazole derivatives of Formula (I), and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists for the RUP25 receptor. Also provided by the present in

Pyrazole derivatives as partial agonists for the nicotinic acid receptor

Nicotinic acid as a hypolipidemic agent appears unique due to its potential to increase HDL cholesterol levels to a greater extent than other drugs. However, it has some side effects, among which severe skin flushing is the most frequent and often limits patients' compliance. In a search for novel agonists for the recently identified and cloned G protein-coupled nicotinic acid receptor, we synthesized a series of substituted pyrazole-3-carboxylic acids that proved to have substantial affinity for this receptor. The affinities were measured by inhibition of [3H] nicotinic acid binding to rat spleen membranes. Potencies and intrinsic activities relative to nicotinic acid were determined by their effects on [35S]GTPγS binding to rat adipocyte and spleen membranes. Interestingly, most compounds were partial agonists. In particular, 2-diazabicyclo-[3,3,O 4,8]octa-3,8-diene-3-carboxylic acid (4c) and 5-propylpyrazole-3-carboxylic acid (4f) proved active with Ki values of approximately 0.15 μM and EC50 values of approximately 6 μM, while their intrinsic activity was only ～50% when compared to nicotinic acid. Even slightly more active was 5-butylpyrazole-3-carboxylic acid (4g) with a Ki value of 0.072 μM, an EC50 value of 4.12 μM, and a relative intrinsic activity of 75%. Of the aralkyl derivatives, 4q (5-(3-chlorobenzyl)pyrazole-3-carboxylic acid) was the most active with a relatively low intrinsic activity of 39%. Partial agonism of the pyrazole derivatives was confirmed by inhibition of G protein activation in response to nicotinic acid by these compounds. The pyrazoles both inhibited the maximum effect elicited by 100 μM nicotinic acid and concentration dependently shifted nicotinic acid concentration-response curves to the right, pointing to a competive mechanism of action.