62182-54-1

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester is used as a chiral building block for the synthesis of drugs targeting the central nervous system. Its unique structure allows for the creation of biologically active molecules with potential therapeutic effects.
Used in Organic Synthesis:
(2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester is used as a key intermediate in the synthesis of complex organic compounds. Its versatility and reactivity make it a valuable component in the development of new chemical entities.
Used in Peptidomimetics Research:
(2S,3S)-3-hydroxy-1,2-Pyrrolidinedicarboxylic acid, 1-(phenylmethyl) ester is studied for its potential as a building block for peptidomimetics, which are compounds that mimic the structure and function of peptides. This research could lead to the development of novel therapeutic agents with improved pharmacological properties.

Upstream product

• 4298-08-2 trans-3-hydroxy-L-proline 
• 501-53-1 benzyl chloroformate 
• 31139-36-3 dibenzyl dicarbonate 

Downstream Products

• 1017576-13-4 N-CBZ-(3S)-3-hydroxprolinamide 
• 412279-18-6 (2S,3S)-3-hydroxypyrrolidin-2-carboxamide 
• 496841-04-4 methyl (2S,3S)-3-hydroxypyrrolidine-2-carboxylate 
• 441718-01-0 1-benzyloxycarbonyl-(2R)-tert-butyldimethylsilyloxymethyl-(3S)-hydroxypyrrolidine 
• 944270-01-3 C₂₀H₂₁NO₅ 
• 1174654-10-4 3-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 

Relevant academic research and scientific papers

PCSK9 ANTAGONIST COMPOUNDS

Disclosed are compounds of Formula (A), or a pharmaceutically acceptable salt thereof: where A, X, R1, and R2 are as defined herein, which compounds have properties for antagonizing PCSK9. Also described are pharmaceutical formulations comprising the compounds of Formula (I) or their salts, and methods of treating cardiovascular disease and conditions related to PCSK9 activity, e.g. atherosclerosis, hypercholesterolemia, coronary heart disease, metabolic syndrome, acute coronary syndrome, or related cardiovascular disease and cardiometabolic conditions.

PCSK9 ANTAGONIST COMPOUNDS

Disclosed are compounds of Formula (I), or a pharmaceutically acceptable salt thereof: (I) wherein A, A1, A2, R1, R2 and R3 are as defined herein, which compounds have properties for antagonizing PCSK9. Also described are pharmaceutical formulations comprising the compounds of Formula I or their salts, and methods of treating cardiovascular disease and conditions related to PCSK9 activity, e.g. atherosclerosis, hypercholesterolemia, coronary heart disease, metabolic syndrome, acute coronary syndrome, or related cardiovascular disease and cardiometabolic conditions.

Second basic pKa: An overlooked parameter in predicting phospholipidosis-inducing potential of diamines

In this paper, we present the phospholipidosis-inducing potential (PLIP) of forty fragment-sized diamines derived from N-benzyl-4-(methylamino)piperidine and discuss the relationship between their PLIP and the physicochemical properties. Our results demonstrate that the previously reported methods are not suitable for predicting the PLIP of fragment-sized diamines; the second basic pKa can distinguish PLIP-positive diamines from PLIP-negative diamines more accurately than ClogP or most basic pKa. To the best of our knowledge, this is the first report describing the relationship between PLIP and second basic pKa.

PCSK9 ANTAGONIST COMPOUNDS

Disclosed are compounds of Formula I, or a salt thereof: where A, B, D, X, R1, R2 and R8 are as defined herein, which compounds have properties for antagonizing PCSK9. Also described are pharmaceutical formulations comprising the compounds of Formula I or their salts, and methods of treating cardiovascular disease and conditions related to PCSK9 activity, e.g. atherosclerosis, hypercholesterolemia, coronary heart disease, metabolic syndrome, acute coronary syndrome, or related cardiovascular disease and cardiometabolic conditions.

PYRROLOBENZODIAZEPINE COMPOUNDS

The invention relates to pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) of formula (I) and in particular to PBD dimers linked through the C1 position, and PBD monomers linked through the C1 position to aromatic groups, and pharmaceutically acceptable salts the

Chemoselective synthesis of N-protected alkoxyprolines under specific solvation conditions

N-Protected hydroxyprolines (Hyp) were transformed chemoselectively into alkoxyproline derivatives by direct O-alkylation. The starting Hyp was transformed into the corresponding dianion in a mixture of dimethyl sulfoxide and tetrahydrofuran (1:16 v/v) as solvent. Under these conditions, the carboxy-anion showed reduced nucleophilicity because it was specifically solvated, and the more reactive oxy-anion was selectively alkylated. N-Protected trans-4-alkoxy-, cis-4-alkoxy- and trans-3-alkoxyprolines were thus obtained in a single step in very high overall yields and with complete stability of the stereogenic center configuration. Copyright

Protected aminooxyprolines for expedited library synthesis: Application to Tsg101-directed proline-oxime containing peptides

The stereoselective synthesis of aminooxy-containing proline analogues bearing Fmoc/Boc or Fmoc/Mtt protection that renders them suitable for incorporation into peptides using Fmoc protocols is reported. Acid-catalyzed unmasking at the completion of peptide synthesis yields free aminooxy-functionalities for oxime formation through reaction with libraries of aldehydes. This allows post solid-phase diversification strategies that may facilitate structure-activity relationship studies.

NOVEL INHIBITORS OF BETA-LACTAMASE

A class of 7-oxo-2,6-diazabicyclo-[3.2.0]-heptane-6-sulfonic acid compounds substituted at the two position of the bicyclic ring with a heterocyclylaminocarbonyl group or a carbocyclylaminocarbonyl group are β-lactamase inhibitors. The compounds and their prodrugs and pharmaceutically acceptable salts are useful in the treatment of bacterial infections in combination with β-lactam antibiotics. In particular, the compounds are suitable for use with β-lactam antibiotics (e.g., imipenem and ceftazidime) against micro-organisms resistant to β-lactam antibiotics due to the presence of the β-lactamases.

N-(5-MEMBERED AROMATIC RING)-AMIDO ANTI-VIRAL COMPOUNDS

Disclosed are compounds having Formula (I) and the compositions and methods thereof for treating or preventing a viral infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R2, m, R, V, W, T, Z, R

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.