17193-39-4

Basic information

• Product Name: H-CHA-OME HCL
• Synonyms: BETA-CYCLOHEXYL-L-ALANINE METHYL ESTER HYDROCHLORIDE;H-CHA-OME HCL;L-CYCLOHEXYLALANINE METHYL ESTER HCL;L-2-AMINO-3-CYCLOHEXYL-PROPIONIC ACID METHYL ESTER HYDROCHLORIDE;L-2-AMINO-3-HEXAHYDROPHENYLPROPIONIC ACID METHYL ESTER HYDROCHLORIDE;3-CYCLOHEXYL-L-ALANINE METHYL ESTER HYDROCHLORIDE;(S)-(-)-Cyclohexylalanine methyl ester hydrochloride;(S)-Methyl 2-aMino-3-cyclohexylpropanoate hydrochloride
• CAS NO: 17193-39-4
• Molecular Formula: C₁₀H₁₉NO₂*ClH
• Molecular Weight: 221.72
• Mol File: 17193-39-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: H-CHA-OME HCL(CAS DataBase Reference)
• NIST Chemistry Reference: H-CHA-OME HCL(17193-39-4)
• EPA Substance Registry System: H-CHA-OME HCL(17193-39-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Hazardous Substances Data: 17193-39-4(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
H-CHA-OME HCL is used as a chemical catalyst for the production of plastics, facilitating the polymerization process and improving the efficiency of plastic manufacturing.
Used in Pharmaceutical Industry:
H-CHA-OME HCL is used as an active pharmaceutical ingredient or a precursor in the synthesis of new medications, leveraging the properties of hydrochloric acid and oxymetazoline to develop innovative therapeutic agents.
Used in Cleaning Agents:
H-CHA-OME HCL is used as a cleaning agent for various applications, capitalizing on the strong acidic nature of hydrochloric acid to remove stains, scale, and other deposits effectively.
Used in Nasal Decongestant Formulations:
In the pharmaceutical sector, H-CHA-OME HCL is used as a key ingredient in nasal decongestant sprays, taking advantage of the vasoconstrictive properties of oxymetazoline to alleviate nasal congestion.
Used in Specialty Chemicals Synthesis:
H-CHA-OME HCL is utilized as a building block or intermediate in the synthesis of specialty chemicals, where its unique combination of components can lead to the creation of novel compounds with specific applications in various industries.
Overall, H-CHA-OME HCL's diverse applications highlight its potential as a multifunctional compound in chemical, pharmaceutical, and industrial processes.

Upstream product

• 63-91-2 L-phenylalanine 
• 98105-41-0 methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 67-56-1 methanol 
• 37736-82-6 (S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid 
• 25528-71-6 (S)-2-amino-3-cyclohexylpropionic acid hydrochloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 27527-05-5 L-cyclohexylalanine 

Downstream Products

• 123381-13-5 N-Triphenylmethyl-cyclohexylalanine methyl ester 
• 741271-70-5 (S)-methyl 2-(trifluoroacetyl)amino-3-cyclohexylpropanoate 
• 40203-89-2 β-cyclohexyl-L-alanine methyl ester isocyanate 
• 157864-46-5 methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate 
• 1033882-08-4 (S)-methyl 3-cyclohexyl-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)propanoate 
• 1469996-58-4 methyl (2S)-2-[[2-(benzyloxy)(5-chlorobenzoyl)amino]-3-cyclohexyl]propanoate 
• 1227477-18-0 C₂₃H₂₄ClF₃N₂O₃ 
• 1227477-20-4 C₂₂H₂₄BrClN₂O₃ 
• 1469996-65-3 (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-cyclohexylpropanoic acid 
• 1469996-70-0 2-(benzyloxy)-5-chloro-N-[(2S)-1-[(3-trifluoromethylphenyl)amino]-1-oxo-3-cyclohexylpropan-2-yl]benzamide 
• 1469996-72-2 2-(benzyloxy)-5-chloro-N-[(2S)-1-[(4-bromophenyl)amino]-1-oxo-3-cyclohexylpropan-2-yl]benzamide 
• 1467641-79-7 C₂₈H₄₄N₃O₈P 
• 1467641-81-1 C₂₆H₄₀N₃O₈P 
• 1467641-83-3 C₃₂H₅₂N₃O₈P 

Relevant articles and documents

Structure-Based Design of Inhibitors Selective for Human Proteasome β2c or β2i Subunits

Subunit-selective proteasome inhibitors are valuable tools to assess the biological and medicinal relevance of individual proteasome active sites. Whereas the inhibitors for the β1c, β1i, β5c, and β5i subunits exploit the differences in the substrate-binding channels identified by X-ray crystallography, compounds selectively targeting β2c or β2i could not yet be rationally designed because of the high structural similarity of these two subunits. Here, we report the development, chemical synthesis, and biological screening of a compound library that led to the identification of the β2c- and β2i-selective compounds LU-002c (4; IC50 β2c: 8 nM, IC50 β2i/β2c: 40-fold) and LU-002i (5; IC50 β2i: 220 nM, IC50 β2c/β2i: 45-fold), respectively. Co-crystal structures with β2 humanized yeast proteasomes visualize protein-ligand interactions crucial for subunit specificity. Altogether, organic syntheses, activity-based protein profiling, yeast mutagenesis, and structural biology allowed us to decipher significant differences of β2 substrate-binding channels and to complete the set of subunit-selective proteasome inhibitors.

Structure-guided design and optimization of dipeptidyl inhibitors of norovirus 3CL protease. Structure-activity relationships and biochemical, X-ray crystallographic, cell-based, and in vivo studies

Norovirus infection constitutes the primary cause of acute viral gastroenteritis. There are currently no vaccines or norovirus-specific antiviral therapeutics available for the management of norovirus infection. Norovirus 3C-like protease is essential for viral replication, consequently, inhibition of this enzyme is a fruitful avenue of investigation that may lead to the emergence of antinorovirus therapeutics. We describe herein the optimization of dipeptidyl inhibitors of norovirus 3C-like protease using iterative SAR, X-ray crystallographic, and enzyme and cell-based studies. We also demonstrate herein in vivo efficacy of an inhibitor using the murine model of norovirus infection.

Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation

Substituting N-methylpyrrole for N-methyindole in secondary-amine-catalysed Friedel-Crafts reactions leads to a curious erosion of enantioselectivity. In extreme cases, this substrate dependence can lead to an inversion in the sense of enantioinduction. Indeed, these closely similar transformations require two structurally distinct catalysts to obtain comparable selectivities. Herein a focussed molecular editing study is disclosed to illuminate the structural features responsible for this disparity, and thus identify lead catalyst structures to further exploit this selectivity reversal. Key to effective catalyst re-engineering was delineating the non-covalent interactions that manifest themselves in conformation. Herein we disclose preliminary validation that intermolecular aromatic (CH-π and cation-π) interactions between the incipient iminium cation and the indole ring system is key to rationalising selectivity reversal. This is absent in the N-methylpyrrole alkylation, thus forming the basis of two competing enantio-induction pathways. A simple L-valine catalyst has been developed that significantly augments this interaction.

Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines

Variously substituted 2-hydroxy-N-(arylalkyl)benzamides were prepared and screened for antiproliferative and cytotoxic activity in cancer cell lines in vitro. Five compounds, out of 33 showed single-digit micromolar IC50 values against several human cancer cell lines. One of the most potent compounds N-((R)-1-(4-chlorophenylcarbamoyl)-2-phenylethyl)-5-chloro-2-hydroxybenzamide (6k) reduced proliferation and induced apoptosis in the melanoma cell line G361 in a dose-dependent manner, as shown by decrease in 5-bromo-2′- deoxyuridine incorporation and increase in several apoptotic markers, including subdiploid population increase, activation of caspases and site-specific poly-(ADP-ribose)polymerase (PARP) cleavage.

Rhodium/graphite-catalyzed hydrogenation of carbocyclic and heterocyclic aromatic compounds

Rhodium on graphite (Rh/Gr, C24Rh) was prepared by reaction of anhydrous rhodium trichloride with potassium graphite (C8K, 3 equivalents) and used as a heterogeneous catalyst for the hydrogenation of carbocyclic and heterocyclic aromatic compounds at room temperature and 1 atm of hydrogen pressure. The effect of substitution on the benzene ring was examined in a variety of derivatives, including those with alkyl, hydroxy, alkoxy, aryloxy, carboxy, amino, nitro, acyl, chloro, or functionalized alkyl groups. Reduction of carbonyl functions of aromatic aldehydes and ketones occurred with complete or partial cleavage of the benzylic C-O bond; this cleavage also occurred in the hydrogenation of benzylic alcohols and esters. Georg Thieme Verlag Stuttgart.

Direct platination as a route to conformationally restricted enantiopure C2-symmetric bisoxazoline pincer complexes

(S)-3-Amino-4-cyclohexyl-2-methylbutan-2-ol 10 was synthesised in four-steps from (S)-2-amino-3-cyclohexanepropanoic acid (47% overall yield). Reaction of 10 with 1,3-bis(ethyl carboximidate)benzene gave (S,S)-1,3-bis(4′-cyclohexylmethyl-5

Reductions of aromatic amino acids and derivatives

Catalytic reduction of phenylalanine and phenylglycine derivatives can be achieved with rhodium on carbon or alumina to give good yields of the corresponding cyclohexyl derivatives. The procedure can be scaled.

Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

The hydrogenation of carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various α-amino and α-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields of the desired amino alcohols and diols were obtained without racemization. The most suitable α-substituents were NH2, NHR, and OH, whereas β-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was found for α-NR2, α-OR, and unfunctionalized esters; acids and amides were also not reduced under these conditions. A working hypothesis for the mode of action of the catalyst is presented.

Enantiospecific Synthesis of N-9-Phenylfluoren-9-yl-α-amino Ketones

Enantiomerically pure N-(9-phenylfluoren-9-yl)-α-amino ketones were prepared in excellent yields by acylation of organolithium reagents with N-(9-phenylfluoren-9-yl)-α-amino acid-derived oxazolidinones. The method is not applicable for the acylation of Grignard reagents as they attack the methylenic carbon of the oxazolidinone to give the corresponding N-alkylated amino acids 13 in excellent yields. The resulting N-(9-phenylfluoren-9-yl)-α-amino ketones 8 could be stereoselectively reduced to the corresponding syn- or anti-β-amino alcohols depending upon the nature of the reducing agent.