1988779-13-0

Basic information

• Product Name: (1S,2R,3S,4R,1'S)-3-[(1-amino-2'-ethyl)butyl]-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxycyclopentane-1-carboxylic acid methyl ester
• CAS NO: 1988779-13-0
• Molecular Weight: 358.478
• Mol File: 1988779-13-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1S,2R,3S,4R,1'S)-3-[(1-amino-2'-ethyl)butyl]-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxycyclopentane-1-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3S,4R,1'S)-3-[(1-amino-2'-ethyl)butyl]-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxycyclopentane-1-carboxylic acid methyl ester(1988779-13-0)
• EPA Substance Registry System: (1S,2R,3S,4R,1'S)-3-[(1-amino-2'-ethyl)butyl]-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxycyclopentane-1-carboxylic acid methyl ester(1988779-13-0)

Safety Data

• Hazardous Substances Data: 1988779-13-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1S,2R,3S,4R,1'S)-3-[(1-amino-2'-ethyl)butyl]-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxycyclopentane-1-carboxylic acid methyl ester" is an amino acid derivative with a complex molecular structure. It consists of a cyclopentane ring with a hydroxyl group and a carboxylic acid group attached to it. The compound also contains an amino acid side chain that terminates in a butyl group and an ethyl group. Additionally, a methyl ester group and a carbonyl group are present. The chemical's stereochemistry is described by the (1S,2R,3S,4R,1'S) configuration, indicating the specific arrangement of the substituent groups in the molecule.

Upstream product

• 229613-93-8 (+)-methyl (3aR,4R,6S,6aS)-4-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-6-carboxylate 
• 97-96-1 2-Ethylbutyraldehyde 
• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 

Downstream Products

• 229614-05-5 (-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-[(tert-butoxycarbonyl)amino]-2-hydroxycyclopentanecarboxylate 
• 229614-55-5 peramivir 
• 229614-56-6 peramivir 
• 229615-05-8 (-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate 

Relevant articles and documents

Peramivir impurity A and impurity C, and preparation methods and application thereof

The invention discloses a peramivir impurity A and a peramivir impurity C with structures as shown in the specification. The invention also provides synthesis methods of the impurity A and the impurity C, and application of the impurity A and the impurity C as impurity reference substances in quality control of peramivir or a pharmaceutical composition thereof. The impurities can be stably prepared and supplied, and a basis is provided for related research and contrast. The peramivir impurity A and the peramivir impurity C disclosed by the invention have important significance in controlling peramivir raw material medicines and researching impurities of preparations of the peramivir raw material medicines.

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.

(1S, 2S, 3S, 4R)-3-Y(1S)-1-ACETYLAMINO-2-ETHYL-BUTYL¨-4-GUANIDINO-2- HYDROXYL-CYCLOPENTYL-1-CARBOXYLIC ACID HYDRATES AND PHARMACEUTICAL USES THEREOF

The present invention relates to (1S,2S,3S,4R)-3-[(1S)-1-acetylamino-2-ethyl-butyl]-4-guanidino-2-hydroxy-cyclopentyl-1-carboxylic acid hydrates compounds, preparing methods thereof, pharmaceutical compositions containing said compounds and preparing methods thereof, and the clinical uses of said compounds as neuramidinase inhibitors for anti-influenza.