293297-95-7

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 81658-26-6 tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate 
• 34837-55-3 Phenylselenyl bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 96014-55-0 Methyl (4S)-4-(N-(tert-Butoxycarbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)pentanoate 
• 39538-20-0 (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 5-methyl ester 
• 126587-35-7 methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-hydroxypentanoate 
• 45214-91-3 (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 
• 106191-02-0 (S)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one 

Downstream Products

• 220623-07-4 (1S,2S,5R)-tert-butyl 3-aza-4-oxo-2-<(1,1,2,2-tetramethyl-1-silapropoxy)methyl>bicyclo<3.1.0>hexane-3-carboxylate 
• 1092504-90-9 N-({(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methyl)-1,3-benzoxazol-2-amine 
• 1092506-44-9 C₁₇H₁₉N₃OS 
• 1092506-43-8 {(1S,2S,5R)-3-[(2-methyl-5-phenyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methanol 
• 1622235-69-1 (2S,3R)-3-(3-carboxy-5-hydroxyphenyl)pyrrolidine-2-carboxylic acid trifluoroacetic acid 
• 1622235-85-1 (2S,3R)-3-(3-([1,1′-biphenyl]-3-ylmethoxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid 
• 1622154-08-8 (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid 
• 1622235-84-0 (2S,3R)-1-(tert-butoxycarbonyl)-3-(3-carboxy-5-propoxyphenyl)-pyrrolidine-2-carboxylic acid 
• 1622235-81-7 (2S,3R)-tert-butyl 3-(3-([1,1′-biphenyl]-3-ylmethoxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)-pyrrolidine-1-carboxylate 
• 1622235-80-6 (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 1622235-79-3 (2S,3R)-tert-butyl 2-(hydroxymethyl)-3-(3-(hydroxymethyl)-5-propoxyphenyl)pyrrolidine-1-carboxylate 
• 1622235-77-1 (2S,3R)-tert-butyl 3-(3-([1,1′-biphenyl]-3-ylmethoxy)-5-(((tertbutyldimethylsilyl)oxy)methyl)-phenyl)-2-(((tert-butyldimethylsilyl)-oxy)methyl)pyrrolidine-1-carboxylate 
• 1622235-76-0 (2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(((tert-butyldimethylsilyl)-oxy)methyl)phenyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-pyrrolidine-1-carboxylate 
• 1622235-66-8 (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)pyrrolidine-2-carboxylic acid hydrochloride 

Relevant academic research and scientific papers

Structure-Activity Relationship Study of Ionotropic Glutamate Receptor Antagonist (2S,3R)-3-(3-Carboxyphenyl)pyrrolidine-2-carboxylic Acid

Herein we describe the first structure-activity relationship study of the broad-range iGluR antagonist (2S,3R)-3-(3-carboxyphenyl)pyrrolidine-2-carboxylic acid (1) by exploring the pharmacological effect of substituents in the 4, 4′, or 5′ positions and the bioisosteric substitution of the distal carboxylic acid for a phosphonic acid moiety. Of particular interest is a hydroxyl group in the 4′ position 2a which induced a preference in binding affinity for homomeric GluK3 over GluK1 (Ki = 0.87 and 4.8 μM, respectively). Two X-ray structures of ligand binding domains were obtained: 2e in GluA2-LBD and 2f in GluK1-LBD, both at 1.9 ? resolution. Compound 2e induces a D1-D2 domain opening in GluA2-LBD of 17.3-18.8° and 2f a domain opening in GluK1-LBD of 17.0-17.5° relative to the structures with glutamate. The pyrrolidine-2-carboxylate moiety of 2e and 2f shows a similar binding mode as kainate. The 3-carboxyphenyl ring of 2e and 2f forms contacts comparable to those of the distal carboxylate in kainate.

Functionalized pyrrolidine inhibitors of human type II α-mannosidases as anti-cancer agents: Optimizing the fit to the active site

Refining the chemical structure of functionalized pyrrolidine-based inhibitors of Golgi α-mannosidase II (GMII) to optimize binding affinity provided a lead molecule that demonstrated nanomolar competitive inhibition of α-mannosidases II and an optimal fit in the active site of Drosophila GMII by X-ray crystallography. Esters of this lead compound also inhibited the growth of human glioblastoma and brain-derived endothelial cells more than the growth of non-tumoral human fibroblasts, suggesting their potential for anti-cancer therapy.

CYCLOPROPYL PYRROLIDINE OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to cyclopropyl proline bis-amide compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

Synthesis and analysis of the sterically constrained L-glutamine analogues (3S,4R)-3,4-dimethyl-L-glutamine and (3S,4R)-3,4-dimethyl-L-pyroglutamic acid

The nonproteinogenic amino acids (3S,4R)-3,4-dimethyl-L-pyroglutamic acid and (3S,4R)-3,4-dimethyl-L-glutamine - found in the cyclic depsipeptides callipeltin B, callipeltin A, and papuamide A - were synthesized from a common intermediate derived from L-pyroglutamic acid. The diastereoselective introduction of the methyl groups was accomplished by cuprate addition and enolate alkylation, followed by a kinetic epimerization of the C-4 methyl substituent. (3S,4R)-3,4-Dimethyl-L-glutamine shows a conformational restriction of its side chain which may be related to its biological function in the natural products where it is found.

Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N- boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

We describe the photoinduced addition of methanol to 5(S)-5- triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-5- triisopropylsiloxymethyl-4(S)-hydroxymethyl-pyrrolidine-2-one, and conversion of this into a variety of 4(S), 5(S)-pyrrolidine-2-ones. Photo-induced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-(R)-N-boc-amino]ethyl- tetrahydrofuran-2-one via rearrangement of the initial photoadduct.

Synthesis of Four Diastereomeric L-2-(Carboxycyclopropyl)glycines. Conformationally Constrained L-Glutamate Analogues

To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereochemically L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues o