155075-23-3

Usage

Uses

Used in Pharmaceutical Research:
N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER is used as a key intermediate in the synthesis of complex organic molecules and pharmaceuticals. Its unique structure allows for the development of novel drug candidates with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER is used as a building block for the creation of various organic compounds. Its versatility and reactivity make it a valuable component in the synthesis of a wide range of molecules.
Used in Protein and Peptide Structure Studies:
N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER is utilized as a model compound in the study of protein and peptide structures. Its unique properties enable researchers to gain insights into the folding, stability, and function of biological macromolecules, contributing to a better understanding of their roles in biological systems.
Used in Drug Development:
N-CBZ-CIS-4-HYDROXY-D-PROLINE METHYL ESTER is employed as a precursor in the development of new pharmaceuticals. Its potential applications in medicinal chemistry include the design of drugs targeting specific biological pathways or receptors, leading to the discovery of innovative therapeutic agents.

Upstream product

• 501-53-1 benzyl chloroformate 
• 114676-59-4 (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride 
• 186581-53-3 diazomethane 
• 130930-25-5 (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 74-88-4 methyl iodide 
• 7732-18-5 water 
• 584-08-7 potassium carbonate 
• 2584-71-6 cis-hydroxy-D-proline 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 444313-67-1 (1R,4R)-5-acetyl-2-oxa-5-azabicyclo[2.2.1]heptan-3-one 
• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 51-35-4 4R-4-hydroxyproline 
• 36901-86-7 cis-hydroxy-D-proline 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 178488-33-0 (2R,4R)-4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 79433-95-7 (2R,4S)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate 
• 787615-47-8 (2R,4R)-N-1-(benzyloxycarbonyl)-4-azidoproline methyl ester 
• 787615-58-1 (2R,4R)-N-1-(benzyloxycarbonyl)-4-(tert-butyloxycarbonylamino)pyrrolidin-2-methanol 
• 787615-48-9 (2R,4R)-N-1-(benzyloxycarbonyl)-4-(tert-butyloxycarbonylamino)proline methyl ester 
• 787615-50-3 N-1-(benzyloxycarbonyl)-(4R)-(tert-butyloxycarbonylamino)-(2R)-(O-mesylmethyl)pyrrolidine 
• 787615-52-5 N-1-(benzyloxycarbonyl)-(4R)-(tert-butyloxycarbonylamino)-(2R)-(thymin-1-ylmethyl)pyrrolidine 
• 787640-34-0 (2R,4R)-1-benzyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate 
• 171181-00-3 N-Cbz-trans-4-(2-naphthyloxy)-D-proline methyl ester 
• 1448706-35-1 C₂₁H₂₀N₂O₈ 
• 1448706-19-1 C₂₂H₂₃Cl₂N₃O₂S 
• 1448706-20-4 C₂₃H₂₅Cl₂N₃O₂S 
• 1448706-36-2 (2R,4S)-2-hydroxymethyl-4-hydroxy-N-(carbobenzyloxy)pyrrolidine 
• 1018987-47-7 C₅H₁₁NO₂*ClH 

Relevant academic research and scientific papers

Spiegelmeric 4R/S-hydroxy/amino-L/D-prolyl collagen peptides: conformation and morphology of self-assembled structures

The primary structure of collagen, the major protein in connective tissue of mammals, comprises of repeating triads [(LPro-LHyp-Gly)n, P1, LHyp being 4R-hydroxy-lProline)] in a single strand that adopts left-handed polyproline II type helix. Three such single stranded helices wind around each another and held together by interchain H-bonds to form right-handed triple helix. This manuscript reports on collagen derived from its mirror image triad [(DPro-DHyp-Gly)n, P2, DHyp being 4S-hydroxy-DProline) and its 4-amino analogue (DPro-DAmp-Gly)n P4, DAmp being 4S-amino-DProline that form corresponding spiegelmeric triplexes. The amino L-collagen peptide (LPro-LAmp-Gly)n P3 and its D-analogue P4 show higher thermal stabilities compared to 4-hydroxy-lProline collagen peptides P1 and P2. The enantiomeric peptide pairs show mirror image CD profiles and identical thermal stability, with ionizable 4-amino group in P3 and P4 imparting pH dependent triplex stability. Upon cold mixing of the L- and D-collagen peptides, different morphological nanostructures arise from inter triplex peptide association. When the peptides are hot mixed (annealed), the inter peptide association occurs via interaction of single stranded peptide chains of opposite handedness leading to networked gel formation in P1 and P2, while the charged peptides P3 and P4 show more ordered nanofibers, different from the enantiomerically pure peptides. The nanocomposites of such chiral hybrid peptides may have not only interesting physicomorphology, but also biological properties that need exploration.

DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE

Provided herein are a dihydropyrimidine compound and use as a medicament, especially application as a medicament used for treating and preventing hepatitis B. Specifically, provided herein is a compound having Formula (I) or (Ia), or a stereisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is use of the compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof as a medicament, especially use as a medicament for treating and preventing hepatitis B.

Dihydropyridine compound and application thereof to drugs

The invention relates to a dihydropyridine compound and application of the dihydropyridine compound serving as a drug, in particular to application of the dihydropyridine compound serving as a drug for treating and preventing hepatitis B. Specifically, the invention relates to the compound shown as the general formula (I) or (Ia) (please see the specifications for the general formula (I) or (Ia))or stereoisomers, tautomer, a nitrogen oxide, solvate, metabolites and medically acceptable salt of the compound or a prodrug of the compound, wherein all variables are defined in the specification. The invention further relates to application of the compound shown as the general formula (I) or (Ia) or enantiomers, non-enantiomers, the tautomer, hydrates, the solvate or the medically acceptable salt of the compound serving as drugs, in particular to application of the compound or the enantiomers, the non-enantiomers, the tautomer, the hydrates, the solvate or the medically acceptable salt of the compound serving as the drugs for treating and preventing hepatitis B.

PHENYL AMINO PYRIMIDINE BICYCLIC COMPOUNDS AND USES THEREOF

The present invention relates to phenyl amino pyrimidine bicyclic compounds formula (I) which are inhibitors of protein kinases including JAK kinases. In particular the compounds are active against JAK1, JAK2, JAK3 and TYK2 kinases. The kinase inhibitors can be used in the treatment of kinase associated diseases such as immunological and inflammatory diseases including organ transplants; hyperproliferative diseases including cancer and myeloproliferative diseases; viral diseases; metabolic diseases; and vascular diseases.

Structure guided design of a series of sphingosine kinase (SphK) inhibitors

Sphingosine-1-phosphate (S1P) signaling plays a vital role in mitogenesis, cell migration and angiogenesis. Sphingosine kinases (SphKs) catalyze a key step in sphingomyelin metabolism that leads to the production of S1P. There are two isoforms of SphK and observations made with SphK deficient mice show the two isoforms can compensate for each other's loss. Thus, inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable physico-chemical properties to pharmacologically interrogate the role of SphK1 in rodent models and to reproduce the phenotype of SphK1 (-/-) mice.

Structure-guided minimalist redesign of the L-fuculose-1-phosphate aldolase active site: Expedient synthesis of novel polyhydroxylated pyrrolizidines and their inhibitory properties against glycosidases and intestinal disaccharidases

A minimalist active site redesign of the L-fuculose-1-phosphate aldolase from E. coli FucA was envisaged, to extend its tolerance towards bulky and conformationally restricted N-Cbz-amino aldehyde acceptor substrates (Cbz = benzyloxycarbonyl). Various mutants at the active site of the FucA wild type were obtained and screened with seven sterically demanding N-Cbz-amino aldehydes including N-Cbz-prolinal derivatives. FucA F131A showed an aldol activity of 62μmol-1mg-1 with (R)-N-Cbz-prolinal, whereas no detectable activity was observed with the FucA wild type. For the other substrates, the F131A mutant gave aldol activities from 4 to about 25 times higher than those observed with the FucA wild type. With regard to the stereochemistry of the reactions, the (R)-amino aldehydes gave exclusively the anti configured aldol adducts whereas their 5 counterparts gave variable ratios of anti/syn diastereoisomers. Interestingly, the F131A mutant was highly stereoselective both with (R)and with (S)-N-Cbz-prolinal, exclusively producing the anti and syn aldol adducts, respectively. Molecular models suggest that this improved activity towards bulky and more rigid substrates, such as N-Cbz-prolinal, could arise from a better fit of the substrate into the hydrophobic pocket created by the F131A mutation, due to an additional π-cation interaction with the residue K205' and to efficient contact between the substrate and the mechanistically important Y113' and Y209' residues. An expedient synthesis of novel polyhydroxylated pyrrolizidines related to the hyacinthacine and alexine types was accomplished through aldol additions of dihydroxyacetone phosphate (DHAP) to hydroxyprolinal derivatives with the hyperactive FucA F131A as catalyst. The iminocyclitols obtained were fully characterised and found to be moderate to weak inhibitors (relative to 1,4-dideoxy-1,4-imino-L-arabinitol (LAB) and 1,4-dideoxy-1,4-iminoD-arabinitol (DAB)) against glycosidases and rat intestinal saccharidases.

Prolinol-based nucleoside phosphonic acids: new isosteric conformationally flexible nucleotide analogues

trans-4-Hydroxy-l-proline has been used as a starting material for the synthesis of prolinol-based nucleotide analogues with an N-phosphonomethyl moiety attached to the prolinol ring nitrogen atom. The synthetic methodology based on the inversion of configuration at both 1- and 4-position led to all diastereoisomeric O-protected 4-mesyloxyprolinol-N-phosphonates. Alkylation of nucleobases using the synthons in the l-series afforded the nucleotide analogues corresponding to α-l- and β-l-nucleotide. The NMR-based conformational study of these compounds in aqueous solution performed at two different pH values, showing either N-fully protonated or deprotonated forms, revealed the occurrence of the same mostly populated conformer in both cases. All final l-prolinol-based nucleoside phosphonic acids were tested for cytotoxic and antiviral properties, but no significant activity was found.

ANTIBACTERIAL FLUOROQUINOLONE ANALOGS

Compounds having antibacterial activity are disclosed. The compunds have the following structure (I): including stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, wherein A, B, D, E, G, R1, R2, R3, R4, R5, R6 and R7 are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity

The present invention is directed to compounds of the formula I: Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, X, n and the broken lines are as defined herein which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.