229613-83-6

Basic information

• Product Name: (1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate hydrochloride
• Synonyms: 2-Cyclopentene-1-carboxylic acid, 4-aMino-, Methyl ester (hydrochloride)(1:1),(1S,4R)-;Methyl (1S,4R)-4-amino-2-cyclopentene-1-carboxylate hydrochloride;methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
• CAS NO: 229613-83-6
• Molecular Formula: C₇H₁₁NO₂*ClH
• Molecular Weight: 177.62868
• Mol File: 229613-83-6.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate hydrochloride(229613-83-6)
• EPA Substance Registry System: (1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate hydrochloride(229613-83-6)

Safety Data

• Hazardous Substances Data: 229613-83-6(Hazardous Substances Data)

Usage

General Description

"(1S,4R)-Methyl 4-aMinocyclopent-2-enecarboxylate hydrochloride" is a chemical compound containing aminocyclopent-2-ene carboxylate and hydrochloride. It is a molecule with a specific arrangement of atoms, with the (1S,4R) notation indicating the stereochemistry of the molecule. The compound is commonly used in organic synthesis and pharmaceutical research, as it can serve as a building block for the synthesis of various compounds. The hydrochloride salt form of the compound enhances its solubility and stability, making it suitable for use in various experimental and industrial applications. This chemical has the potential to contribute to the development of new drugs and materials.

Upstream product

• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 130931-84-9 (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 75-36-5 acetyl chloride 
• 101752-05-0 methanol hydrochloride 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 67-56-1 methanol 
• 102579-71-5 (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 130931-84-9 (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 1469338-58-6 (1S,2S,3R,4R)-methyl-3-((S)-1-acetamido-2-ethylbutyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-2-(((3-(((E)-3-(3,4-bis(allyloxy)phenyl)acryloyl)oxy)propyl)carbamoyl)oxy)cyclopentanecarboxylate 
• 1113025-22-1 [(4S)-4-(tritylamino)cyclopent-1-en-1-yl]methanol 

Relevant articles and documents

4, 7-DIAZAINDOLE AND 4, 7-DIAZAINDAZOLE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA

The present invention relates to a compound having the formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing influenza.

Peramivir Phosphonate Derivatives as Influenza Neuraminidase Inhibitors

Peramivir is a potent neuraminidase (NA) inhibitor for treatment of influenza infection by intravenous administration. By replacing the carboxylate group in peramivir with a phosphonate group, phosphono-peramivir (6a), the dehydration and deoxy derivatives (7a and 8a) as well as their corresponding monoalkyl esters are prepared from a pivotal intermediate epoxide 12. Among these phosphonate compounds, the dehydration derivative 7a that has a relatively rigid cyclopentene core structure exhibits the strongest inhibitory activity (IC50 = 0.3-4.1 nM) against several NAs of wild-type human and avian influenza viruses (H1N1, H3N2, H5N1, and H7N9), although the phosphonate congener 6a is unexpectedly less active than peramivir. The inferior binding affinity of 6a is attributable to the deviated orientations of its phosphonic acid and 3-pentyl groups in the NA active site as inferred from the NMR, X-ray diffraction, and molecular modeling analyses. Compound 7a is active to the oseltamivir-resistant H275Y strains of H1N1 and H5N1 viruses (IC50 = 73-86 nM). The phosphonate monoalkyl esters (6b, 6c, 7b, 7c, 8b, and 8c) are better anti-influenza agents (EC50 = 19-89 nM) than their corresponding phosphonic acids (EC50 = 50-343 nM) in protection of cells from the viral infection. The phosphonate monoalkyl esters are stable in buffer solutions (pH 2.0-7.4) and rabbit serum; furthermore, the alkyl group is possibly tuned to attain the desired pharmacokinetic properties.

Facile synthesis of the neuraminidase inhibitor peramivir

An improved and convenient synthetic route for the synthesis of peramivir has been developed with a total 34% yield. The process was improved from previous methods in three key reaction steps including 1,3-dipolar cycloaddition, reductive ring cleavage of