426226-35-9

Basic information

• Product Name: (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride)
• Synonyms: (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride);methyl(1R,4S)-4-aminocyclopent-2-ene-1-carboxylatehydrochloride;Methyl (1R,4S)-4-amino-2-cyclopentene-1-carboxylate hydrochloride
• CAS NO: 426226-35-9
• Molecular Formula: C7H12ClNO2
• Molecular Weight: 177.62868
• Mol File: 426226-35-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride)(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride)(426226-35-9)
• EPA Substance Registry System: (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride)(426226-35-9)

Safety Data

• Hazardous Substances Data: 426226-35-9(Hazardous Substances Data)

Usage

Description

(1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride) is an organic compound that serves as an intermediate in the synthesis of ent-Abacavir (A105015), a pharmaceutical agent used in the treatment of HIV infection. It is characterized by its unique stereochemistry and plays a crucial role in the development of anti-HIV drugs.

Uses

Used in Pharmaceutical Industry:
(1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride) is used as a key intermediate in the synthesis of ent-Abacavir (A105015), an enantiomer of Abacavir (A105000). (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride) is an anti-HIV drug that helps in the treatment of HIV infection by acting as a reverse transcriptase inhibitor. It is metabolized in the liver to produce inactive glucuronide and carboxylate metabolites, which contribute to its therapeutic effects.
In the synthesis process, intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which selectively inhibits HIV reverse transcriptase by incorporating into viral DNA. This action helps in preventing the replication of the virus and controlling the progression of the infection.
Overall, (1R,4S)-Methyl 4-aMinocyclopent-2-enecarboxylate (Hydrochloride) is a vital component in the development of anti-HIV drugs, specifically ent-Abacavir, and plays a significant role in the pharmaceutical industry for the treatment of HIV infection.

Upstream product

• 67-56-1 methanol 
• 61865-62-1 cis-4-aminocyclopent-2-nene-1-carboxylic acid hydrochloride 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 

Downstream Products

• 1113025-22-1 [(4S)-4-(tritylamino)cyclopent-1-en-1-yl]methanol 
• 1113025-21-0 methyl (4S)-4-(tritylamino)cyclopent-1-ene-1-carboxylate 
• 905579-51-3 ((1S,2S,4R)-4-(4-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxycyclopentyl)-methyl sulfamate 
• 1113025-24-3 (1S,2S,4R)-2-(hydroxymethyl)-4-(tritylamino)cyclopentanol 
• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 426226-50-8 PMC6 
• 426226-50-8 (1S,3R)-1-(9-adenenyl)-3-(N-hydroxycarbamoyl)cyclopentane 
• 77745-29-0 trans-4-Aminocyclopent-2-enemethanol Hydrochloride 

Relevant articles and documents

The de-guanidinylated derivative of peramivir remains a potent inhibitor of influenza neuraminidase

The guanidine function in the potent neuraminidase inhibitor peramivir was included early on in the drug design process, and examination of X-ray structural data for the enzyme-inhibitor complex would seem to indicate that the guanidine plays a critical r

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.

ENHANCED ANTI-INFLUENZA AGENTS CONJUGATED WITH ANTI-INFLAMMATORY ACTIVITY

Novel dual-targeted, bifunctional anti-influenza drugs formed by conjugation with anti-inflammatory agents are disclosed. Exemplary drugs according to the invention include caffeic acid (CA)-bearing zanamivir (ZA) conjugates ZA-7-CA (1), ZA-7-CA-amide (7) and ZA-7-Nap (43) for simultaneous inhibition of influenza virus neuraminidase and suppression of proinflammatory cytokines. Synthetic methods for preparation of these enhanced anti-influenza conjugate drugs are provided. The synthetic bifunctional ZA conjugates act synergistically towards protection of mice lethally infected by H1N1 or H5N1 influenza viruses. The efficacy of ZA-7-CA, ZA-7-CA-amide and ZA-7-Nap conjugates is much greater than the combination therapy of ZA with anti-inflammatory agents.