1638744-20-3 | (1S,2S)-2-fluorocyclopropan-1-aminehydrochloride

CAS:1638744-20-3 | (1S,2S)-2-fluorocyclopropan-1-aminehydrochloride,Description

“(1S,2S)-2-fluorocyclopropan-1-amine hydrochloride” is likely a chiral compound due to the presence of two stereocenters . It contains a cyclopropane ring, which is a three-membered carbon ring, with a fluorine atom and an amine group attached. The hydrochloride indicates that it is a salt of hydrochloric acid .

Synthesis Analysis

The synthesis of such a compound would likely involve the reaction of a suitable cyclopropane precursor with a fluorinating agent. The stereochemistry could be controlled by using a chiral auxiliary or by performing the reaction under asymmetric conditions .

Molecular Structure Analysis

The molecular structure of this compound would be characterized by the three-membered cyclopropane ring, with the fluorine and amine substituents in a 1,2-relationship . The stereochemistry at the two carbon atoms would be defined by the (1S,2S) descriptor .

Physical And Chemical Properties Analysis

The physical and chemical properties of this compound would depend on its exact structure. Typically, amines are polar and can engage in hydrogen bonding, which can affect their boiling points, solubility, etc .

Scientific Research Applications

Anti-Influenza Virus Activity

Research has identified compounds related to (1S,2S)-2-fluorocyclopropan-1-amine hydrochloride with potential as anti-influenza virus agents. A study highlighted a tricyclic compound incorporating a unique amine moiety, demonstrating potent anti-influenza A virus activity and tolerability in mice, suggesting promise for human application (Oka et al., 2001).

Drug Discovery and Lead Optimization

Investigations into the effects of the trans-fluorine moiety on the hydrolysis rate of certain compounds have led to synthetic access to both diastereomers of the fluorocyclopropyl analog of cabozantinib, a drug for thyroid cancer and renal cell carcinoma. The fluorocyclopropane moiety demonstrated improved in vitro profiles compared to the non-fluorinated structure, indicating its utility in fine-tuning drug properties for lead optimization in drug discovery (Veliks et al., 2020).

Antibacterial Activity

A series of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids demonstrated excellent antibacterial activity, especially against Gram-positive infections. These compounds also showed potent inhibitory activity against bacterial DNA topoisomerase IV, with some having reduced inhibitory activity against human DNA topoisomerase II compared to non-cyclopropane-fused compounds (Inagaki, Takahashi, & Takemura, 2004).

Synthesis of Enantiomerically Pure Amino Acids

Research into the one-pot reaction of methylcyclopropanone acetal with chiral amines and a trialkyl phosphite resulted in the creation of amino phosphonate esters with excellent diastereoselectivities. Following catalytic hydrogenolysis and hydrolysis, (1S,2S)-1-amino-2-methylcyclopropanephosphonic acid was produced in good overall yield and with excellent enantiomeric excess, showcasing a method for synthesizing enantiomerically pure amino acids (Fadel & Tesson, 2000).

Safety And Hazards

The safety and hazards associated with this compound would depend on its specific properties. As with all chemicals, appropriate safety precautions should be taken when handling it to avoid exposure .

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