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Usage

Uses

Used in Pharmaceutical Industry:
1-N-BOC-(2S,4S)-4-HYDROXY-2-(HYDROXYMETHYL) PYRROLIDINE is used as a building block for the synthesis of various drugs and bioactive molecules. Its unique structure and functional groups make it an essential component in the development of new pharmaceuticals and bioactive compounds.
Used in Organic Synthesis:
1-N-BOC-(2S,4S)-4-HYDROXY-2-(HYDROXYMETHYL) PYRROLIDINE is used as a versatile intermediate in organic synthesis, where its stereochemistry and functional groups play a critical role in constructing complex molecules.
Used in Medicinal Chemistry:
1-N-BOC-(2S,4S)-4-HYDROXY-2-(HYDROXYMETHYL) PYRROLIDINE is used as a key intermediate in medicinal chemistry for the development of new pharmaceuticals and bioactive compounds, leveraging its unique structure and functional groups to create innovative drug candidates.

Upstream product

• 121147-94-2 1-tert-butyl 2-methyl (2S,4S)-4-((benzoyl)oxy)-1,2-pyrrolidinedicarboxylate 
• 81102-38-7 cis-L-hydroxyproline methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 168264-25-3 Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester 
• 37813-30-2 (2S,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester 
• 33996-30-4 trans-4-hydroxy-L-proline ethyl ester hydrochloride 
• 1023754-70-2 (2S,4S)-4-formyloxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 1338549-31-7 (2S,4S)-4-tert-butoxycarbonylmethoxy-2-(4-tosyloxymethyl)-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 1338549-37-3 (2S,4S)-2-(N₃-benzoylthymine-1-ylmethyl)-4-tert-butoxycarbonylmethyoxypyrrolidine-1-carboxylic acid tert-butyl ester 
• 1338549-41-9 C₂₈H₃₆N₆O₆ 
• 1338549-45-3 C₂₈H₃₆N₆O₆ 
• 1338549-49-7 (2S,4S)-2-(N₃-benzoylthymine-1-ylmethyl)-4-carboxymethoxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester 

Relevant academic research and scientific papers

SULFONAMIDE COMPOUNDS HAVING TNAP INHIBITORY ACTIVITY

The present invention relates to a compound or a pharmacologically acceptable salt thereof having excellent tissue non-specific alkaline phosphatase inhibitory activity. The present invention provides a compound represented by the formula (I) or a pharmacologically acceptable salt thereof.

Accessible chiral linker to enhance potency and selectivity of neuronal nitric oxide synthase inhibitors

The three important mammalian isozymes of nitric oxide synthase (NOS) are neuronal NOS (nNOS), endothelial NOS (eNOS), and inducible NOS (iNOS). Inhibitors of nNOS show promise as treatments for neurodegenerative diseases. Eight easily synthesized compounds containing either one (20a,b) or two (9a-d; 15a,b) 2-amino-4-methylpyridine groups with a chiral pyrrolidine linker were designed as selective nNOS inhibitors. Inhibitor 9c is the best of these compounds, having a potency of 9.7 nM and dual selectivity of 693 and 295 against eNOS and iNOS, respectively. Crystal structures of nNOS complexed with either 9a or 9c show a double-headed binding mode, where each 2-aminopyridine headgroup interacts with either a nNOS active site Glu residue or a heme propionate. In addition, the pyrrolidine nitrogen of 9c contributes additional hydrogen bonds to the heme propionate, resulting in a unique binding orientation. In contrast, the lack of hydrogen bonds from the pyrrolidine of 9a to the heme propionate allows the inhibitor to adopt two different binding orientations. Both 9a and 9c bind to eNOS in a single-headed mode, which is the structural basis for the isozyme selectivity.

Design, synthesis, and antileukemic activity of stereochemically defined constrained analogues of FTY720 (Gilenya)

FTY720 functions as an immunosuppressant due to its effect on sphingosine-1-phosphate receptors. At doses well above those needed for immunosuppression, FTY720 also has antineoplastic actions. Our published work suggests that at least some of FTY720's anticancer activity is independent of its effects on S1P receptors and due instead to its ability to induce nutrient transporter down-regulation. Compounds that trigger nutrient transporter loss but lack FTY720's S1P receptor-related, dose-limiting toxicity have the potential to be effective and selective antitumor agents. In this study, a series of enantiomerically pure and stereochemically diverse O-substituted benzyl ethers of pyrrolidines was generated and tested for the ability to kill human leukemia cells. The stereochemistry of the hydroxymethyl was found to be a key determinant of compound activity. Moreover, phosphorylation of this group was not required for antileukemic activity.

Influence of 4- or 5-substituents on the pyrrolidine ring of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin derivatives on their inhibitory activities towards caspases-3 and -7 Dedicated to Professor Dr. Ernst-Ulrich Würthwein on the occasion of his 65th birthday

A series of new 4- or 5-substituted pyrrolidine derivatives of 5-[1-(2-methoxymethylpyrrolidinyl)sulfonyl]isatin bearing additional n-butyl or 4-fluorobutyl groups at the isatin nitrogen were prepared and their inhibitory activities have been tested against caspases-3 and -7, which are known to participate in the execution of the programmed cell death, called apoptosis. Several analogues fluorinated at the 4-position of the pyrrolidine ring were also synthesized since such inhibitors might be developed as 18F-radiotracers for molecular imaging of activated caspases in vivo by PET. Enantiomerically pure diastereomeric 4-fluoropyrrolidinyl derivatives inhibited the enzymes in the nanomolar scale, i.e.100-1000 times more efficient than the corresponding 4-methoxy analogues. The 4,4-difluorinated compound showed the best result with IC50 = 362 nM and 178 nM for the aforementioned caspases. In contrast, the 4-methoxy and 4-trifluoromethyl analogues exhibited less inhibition potencies for the enzymes in the μM scale, whereas all 4-OPEG4 (PEG4 = tetraethyleneglycol) and 5-methoxymethyl derivatives were inactive.

Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone

Four isomers of the monomer of peptide nucleic acid (PNA) were derived from (2S,4R)-4-hydroxyproline; they had different stereochemistries at the C 2 and C4 positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C2 and the C4 positions in pyrrolidine ring. The obtained backbone frameworks were reacted with N-benzoyl thymine to give the corresponding PNA monomers. Spectroscopic comparison of the resultant monomers confirmed their stereochemistries.

Dual EGFR/ErbB-2 inhibitors from novel pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines

A novel class of substituted pyrrolidinyl-acetylenic thieno[3,2-d]pyrimidines has been identified that are potent and selective inhibitors of both EGFR/ErbB-2 receptor tyrosine kinases. The inhibitors are found to display a range of enzyme and cellular potency and also to display a varying level of covalent modification of the kinase targets. Selected molecules, including compound 15h, were found to be potent in enzymatic and cellular assays while also demonstrating exposure in the mouse from an oral dose.

Conformationally restrained chiral analogues of spermine: Chemical synthesis and improvements in DNA triplex stability

The synthesis of novel chiral analogues of spermine, 11 (2R,4S) and 14 (2S,4R), is reported starting from trans-4-hydroxy-L-proline 3. These cyclic analogues are generated from linear, achiral spermine by incorporating a pyrrolidine ring on the backbone t