229614-05-5

Usage

Uses

1. Used in Pharmaceutical Industry:
(1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate is used as a key intermediate in the synthesis of novel pharmaceutical compounds for various therapeutic applications. Its unique structure and functional groups make it a promising candidate for the development of new drugs targeting specific biological pathways.
2. Used in Drug Delivery Systems:
The compound can be utilized in the design and development of drug delivery systems, particularly for targeted drug delivery. Its functional groups can be exploited to attach drug molecules or other therapeutic agents, enabling controlled and specific release at the site of action.
3. Used in Chemical Research:
(1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate can be employed as a research tool in chemical and biological studies. Its unique structure and chirality make it an interesting subject for investigations into stereochemistry, molecular recognition, and biological activity.
4. Used in the Preparation of Bifunctional Conjugates:
Similar to the use of 2,3-Diethylpiperazine in the preparation of bifunctional zanamivir conjugates, (1S,2S,3R,4R)-methyl 3-((R)-1-Acetamido-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate can be used as a reagent in the synthesis of bifunctional conjugates with enhanced therapeutic properties. These conjugates could potentially combine the benefits of multiple drugs or therapeutic agents, leading to improved treatment outcomes.

InChI:InChI=1S/C20H36N2O6/c1-8-12(9-2)16(21-11(3)23)15-14(22-19(26)28-20(4,5)6)10-13(17(15)24)18(25)27-7/h12-17,24H,8-10H2,1-7H3,(H,21,23)(H,22,26)/t13-,14+,15+,16?,17+/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 1988779-13-0 (1S,2S,3S,4R)-methyl 3-((S)-1-amino-2-ethylbutyl)-4-(tert-butoxycarbonylamino)-2-hydroxycyclopentanecarboxylate 
• 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 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 168683-02-1 (1S,4R)-(-)-methyl-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopent-2-ene-1-carboxylate 

Downstream Products

• 1352062-19-1 C₁₄H₂₆N₂O₄*ClH 
• 229615-05-8 (-)-methyl (1S,2S,3R,4R)-3-[(1S)-1-(acetylamino)-2-ethylbutyl]-4-amino-2-hydroxycyclopentanecarboxylate 

Relevant academic research and scientific papers

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.

ANTI-INFLUENZA COMPOSITIONS AND METHODS

Disclosed are novel compounds comprising an imino-ribose derivative covalently linked to a carbocycle or heterocycle. Pharmaceutical compositions comprising the compounds of the invention are also described. Methods of inhibition, treatment and/or suppres

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

(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.

Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors

Compounds I-III wherein U is CH, O, or S; Z is mono- or di-substituted carbon; R is (CH2)nCO2H, (CH2)nSO3H, (CH2)nPO3H2, (CH2)nNO2, CH(SCH3)3, esters; R1 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl; RR1 is O; n is 0-4; R2, R3 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl, haloalkyl; R4 is (CH2)nOH, (CH2)nNH2, substituted alkyl were prepd. as neuraminidase inhibitors. Thus, (1R,3R,4R,1′S)-(?)-(1′-acetylamino-2 ′-ethyl)butyl-4-(aminoimino)methylaminocyclopentan-1-carboxylic acid was prepd. and tested in vitro as neuraminidase inhibitor (IC501μM).

Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity

The design and synthesis of novel, orally active, potent, and selective inhibitors of influenza neuraminidase differing structurally from existing neuraminidase inhibitors are described. X-ray crystal structures of complexes of neuraminidase with known five- and six-membered ring inhibitors revealed that potent inhibition of the enzyme is determined by the relative positions of the interacting inhibitor substituents (carboxylate, glycerol, acetamido, hydroxyl) rather than by the absolute position of the central ring. This led us to design potential neuraminidase inhibitors in which the cyclopentane ring served as a scaffold for substituents (carboxylate, guanidino, acetamido, alkyl) that would interact with the four binding pockets of the neuraminidase active site at least as effectively as those of the established six-membered ring inhibitors such as DANA (2), zanamivir (3), and oseltamivir (4). A mixture of the isomers was prepared initially. Protein crystallography of inhibitor - enzyme complexes was used to screen mixtures of isomers in order to identify the most active stereoisomer. A synthetic route to the identified candidate 50 was developed, which featured (3 + 2) cycloaddition of 2-ethylbutyronitrile oxide to methyl (1S,4R)-4[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (43). Structures of the synthetic compounds were verified by NMR spectroscopy using nuclear Overhauser effect methodology. Two new neuraminidase inhibitors discovered in this work, 50 and 54, have IC50 values vs neuraminidase from influenza A and B of 50 values are comparable or superior to those for zanamivir and oseltamivir, agents recently approved by the FDA for treatment of influenza. The synthetic route used to prepare 50 and 54 was refined so that synthesis of pure active isomer 54, which has five chiral centers, required only seven steps from readily available intermediates. Further manipulation was required to prepare deoxy derivative 50. Because the activities of the two compounds are comparable and 54 [RWJ-270201 (BCX-1812)] is the easier to synthesize, it was selected for further clinical evaluation.