84520-68-3

Usage

Uses

Used in Pharmaceutical Industry:
1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate is used as a reagent for the preparation of antibacterial and anti-tuberculosis (TB) tat-peptidomimetics. It contributes to the development of these therapeutic agents by enhancing their efficacy and half-life, making them more effective in combating bacterial infections and tuberculosis.
Used in Peptide Synthesis:
In the field of peptide synthesis, 1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate serves as a key intermediate for the synthesis of complex peptide structures. Its unique azide group allows for efficient click chemistry reactions, enabling the rapid and selective formation of peptide bonds and the assembly of larger biomolecules.
Used in Research and Development:
1-tert-butyl 2-Methyl 4-azidopyrrolidine-1,2-dicarboxylate is also utilized in research and development settings for the exploration of novel therapeutic agents and drug delivery systems. Its unique chemical properties make it a valuable tool for studying the structure-activity relationships of bioactive peptides and for developing new strategies to improve their pharmacokinetic and pharmacodynamic properties.

Upstream product

• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 401564-28-1 N-Boc-(4S)-(benzamido)-L-proline methyl ester 
• 401564-27-0 (2S,4S)-4-benzoylamino-1-tert-butoxycarbonylpyrrolidine-2-carboxylic acid 
• 737765-48-9 (2S,4S)-4-Azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-pentafluorophenyl ester 
• 737765-52-5 C₂₆H₂₇F₅N₁₂O₆ 
• 551929-85-2 (2S,4S)-4-Azido-1-{(2S,3R)-2-[(S)-4-[3-(2-benzyloxycarbonylamino-acetylamino)-4-hydroxy-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyrylamino]-3-hydroxy-butyryl}-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Altering the sex pheromone cyclo(L-pro-l-pro) of the diatom seminavis robusta towards a chemical probe

As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(L-Pro-L-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(L-Pro-L-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide-and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine-and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

Quinoline-Proline, Triazole Hybrids: Design, Synthesis, Antituberculosis, Molecular Docking, and ADMET Studies

A series of novel quinoline-proline hybrids (11a-g) and quinoline-proline-1,2,3-triazole hybrids (12-14) were synthesized by click chemistry based on molecular hybridization concept and were characterized by NMR, mass spectrometry, and elemental analysis. All the titled target compounds were tested for antitubercular activity by MABA and LORA methods by in vitro. Interestingly, two compounds (2R,4S)-1-((2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-methyl)-4-(4-nitrobenzamido)-N-phenylpyrrolidine-2-carboxamide (11b) and (2R,4S)-1-((2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-methyl)-4-(4-fluorobenzamido)-N-phenylpyrrolidine-2-carboxamide (11c) exhibited significant activity against the tested Mycobacterium tuberculosis H37Rv strain. Further, the cytotoxicity (CC50) profile of the titled compounds against the Vero cell was performed and discussed. A molecular docking study of the hit compounds (11b and 11c) was also performed to find their putative binding interaction with the active site of the target proteins. Finally, in silico ADMET properties were also predicted for all the synthesized molecules to evaluate their drug-likeness behavior.

HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formula (I): wherein the variables are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are inhibitors of replication of the hepatitis C virus. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat hepatitis C viral infections, and processes and intermediates useful for preparing such compounds.

Method for Manufacturing Hydroxyl Group Substitution Product

In the present invention, a hydroxyl group substitution product is manufactured by reaction of an alcohol with sulfuryl fluoride (SO2F2) in the presence of an organic base and a nucleophile (X?). The present invention is thus effective as an industrial manufacturing method that uses a relatively cheap reagent suitable for large-scale applications and can be accomplished in a simple process with easy purification operation and less waste generation and is suitably applicable for manufacturing of optically active hydroxyl group substitution products, notably optically active α-hydroxyl group substitution ester and optically active 4-hydroxyl group substitution proline. The manufacturing method of the present invention solves all of the prior art problems and can be applied for industrial uses.

Synthesis and biological activity of 1-phenylsulfonyl-4-phenylsulfonylaminopyrrolidine derivatives as thromboxane A2 receptor antagonists

The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the ω-octenol side chain of thromboxane A2 (TXA2), in reference to the structure of Daltroban. Several compounds were found to be potent TXA2 receptor antagonists. Compound 51a was the most effective inhibitor of 9,11-epoxymethano PGH2 (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM).