188772-70-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-1-(furan-2-yl)propanamine is used as a reagent in the organic synthesis of various pharmaceuticals and bioactive compounds. Its functional groups and stereochemistry allow for the development of new molecules with potential therapeutic applications.
Used in Central Nervous System Research:
(R)-1-(furan-2-yl)propanamine is used as a research compound for studying its potential effects on the central nervous system. It is being investigated for its possible therapeutic role in treating certain neurological disorders.
Used in Drug Development:
(R)-1-(furan-2-yl)propanamine serves as a building block in the development of new drugs, particularly those targeting neurological conditions. Its unique structure and properties make it a promising candidate for the creation of novel therapeutic agents.

Upstream product

• 188772-57-8 (Z)-1-(furan-2-yl)propan-1-one O-benzyloxime 
• 116435-25-7 (Z)-1-(furan-2-yl)propan-1-one oxime 
• 1106778-09-9 C₁₁H₁₉NO₂S 
• 69662-80-2 1-(2-furyl)-1-propanone oxime 
• 3194-15-8 2-propionylfuran 
• 98-01-1 furfural 

Relevant academic research and scientific papers

Asymmetric synthesis of α- And β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines

The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected α- and β-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, α-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α- Disubstituted α-amino esters with high enantiomeric purity can also be prepared when α-imino esters are the starting substrates.

Application of the addition of triorganozincates to N-(tert-butanesulfinyl)imines to the enantioselective synthesis of α-amino acids

Highly enantiomerically enriched N-protected α-amino acids can be easily prepared from optically pure N-(tert-butanesulfinyl)imines by a four-step sequence involving: diastereoselective addition of a triorganozincate to the imine, removal of the sulfinyl group, benzoylation of the nitrogen atom of the obtained primary amine and oxidation of one of the substituents on the carbon atom α to the nitrogen. Using the same configuration in the sulfinyl chiral auxiliary, amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α-Disubstituted α-amino esters with high optical purity can also be prepared by the diastereoselective addition of trialkylzincates to α-imino esters.

Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.

Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5-methylfuran-2-yl) propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): A potent, orally bioavailable CXCR2/CXCR1 receptor antagonist

Structure-activity studies on lead cyclobutenedione 3 led to the discovery of 4 (SCH 527123), a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist with excellent cell-based activity. Compound 4 displayed good oral bioavailability in rat and may be a potential therapeutic agent for the treatment of various inflammatory diseases.

THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).

3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

Novel enantioselective synthesis of both enantiomers of furan-2-yl amines and amino acids

A new enantioselective synthesis of furan-2-yl amines and amino acids is described, in which the key step is the oxazaborolidine-catalyzed enantioselective reduction of O-benzyl (E)- and (Z)-furan-2-yl ketone oximes to the corresponding chiral amines. The chirality of the furan-2-yl amines is fully controlled by the appropriate choice of the geometrical isomer of the O-benzyl oxime. Oxidation of the furan ring furnished amino acids in high yields.