496841-07-7

Usage

Uses

Used in Pharmaceutical Research:
(2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester is employed as a key intermediate in the synthesis of pharmaceuticals, particularly for the development of new drugs and biologically active compounds. Its unique stereochemistry and functional groups contribute to its potential as a building block in medicinal chemistry.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester is used as a versatile reagent for the creation of a variety of complex organic molecules. Its functional groups allow for multiple synthetic pathways, making it a valuable component in the synthesis of diverse chemical libraries.
Used in Drug Development:
(2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester is utilized in drug development as a precursor for the synthesis of potential therapeutic agents. Its specific structural features can be tailored to target specific biological pathways, offering a promising avenue for the creation of new treatments for various diseases.
Used in Organic Chemistry Research:
In the realm of organic chemistry research, (2S,3R)-N-tert-Butoxycarbonyl-3-benzoyloxy-2-pyrrolidinecarboxylic acid methyl ester serves as a model compound for studying reaction mechanisms and exploring new synthetic methodologies. Its complex structure and functional groups provide a rich platform for understanding and advancing the field of organic chemistry.

Upstream product

• 4298-08-2 trans-3-hydroxy-L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1844898-16-3 (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride 

Downstream Products

• 496841-09-9 (2S,3R)-3-hydroxy-2-pyrrolidinecarboxylic acid methyl ester trifluoroacetate 
• 757247-90-8 C₂₃H₃₄ClN₃O₂Si 
• 757247-89-5 (2R,3R)-3-(tert-butyldimethylsilanyloxy)-N-(3-chloro-4-cyano-2-methylphenyl)-2-((S)-1-hydroxy-2-methylpropyl)pyrrolidine-1-carboxamide 
• 945469-40-9 C₂₁H₂₇F₃ClN₃O₂Si 
• 945469-39-6 C₂₁H₂₉F₃ClN₃O₃Si 
• 757247-82-8 (1S,7R,7aR)-2-chloro-4-(7-tert-butyldimethylsilanyloxy-1-trifluoromethyl-3-oxo-hexahydro-pyrrolo[1,2-c]imidazol-2-yl)-3-methyl-benzonitrile 
• 757247-81-7 (2R,3R)-3-(tert-butyldimethylsilanyloxy)-2-[(1R)-(2,2,2-trifluoro-1-hydroxyethyl)]-pyrrolidine-1-carboxylic acid (3-chloro-4-cyano-2-methyl-phenyl)-amide 
• 130966-46-0 (2S,3R)-N-tert-Butyloxycarbonyl-3-hydroxy-2-pyrrolidinecarboxylic Acid Methyl Ester 

Relevant academic research and scientific papers

Discovery of potent and muscle selective androgen receptor modulators through scaffold modifications

A novel series of imidazolin-2-ones were designed and synthesized as highly potent, orally active and muscle selective androgen receptor modulators (SARMs), with most of the compounds exhibiting low nM in vitro potency in androgen receptor (AR) binding and functional assays. Once daily oral treatment with the lead compound 11a (AR Ki = 0.9 nM, EC50 = 1.8 nM) for 14 days induced muscle growth with an ED50 of 0.09 mg/kg, providing approximately 50-fold selectivity over prostate growth in an orchidectomized rat model. Pharmacokinetic studies in rats demonstrated that the lead compound 11a had oral bioavailability of 65% and a plasma half-life of 5.5 h. On the basis of their preclinical profiles, the SARMs in this series are expected to provide beneficial anabolic effects on muscle with minimal androgenic effects on prostate tissue.

Discovery of potent, orally-active, and muscle-selective androgen receptor modulators based on an N-aryl-hydroxybicyclohydantoin scaffold

A novel, N-aryl-bicyclohydantoin selective androgen receptor modulator scaffold was discovered through structure-guided modifications of androgen receptor antagonists. A prototype compound (7R,7aS)-10b from this series is a potent and highly tissue-selective agonist of the androgen receptor. After oral dosing in a rat atrophied levator ani muscle model, (7R,7aS)-10b demonstrated efficacy at restoring levator ani muscle mass to that of intact controls and exhibited >50-fold selectivity for muscle over prostate.

Bicyclic modulators of androgen receptor function

The invention provides for a pharmaceutical composition capable of modulating the androgen receptor comprising a compound of formula I wherein the substitutents are as described herein. Further provided are methods of using such compounds for the treatment of nuclear hormone receptor-associated conditions, such as age related diseases, for example sarcopenia. Also provided are pharmaceutical compositions containing such compounds and processes for preparing some of the compounds of the invention.

BICYCLIC MODULATORS OF ANDROGEN RECEPTOR FUNCTION

The invention provides compounds according to formula I wherein the substitutents are as described herein. Further provided are methods of using such compounds for the treatment of nuclear hormone receptor-associated conditions, such as age related diseases, for example sarcopenia. Also provided are pharmaceutical compositions containing such compounds and processes for preparing some of the compounds of the invention.

Bicyclic modulators of androgen receptor function

The invention provides compounds of the formula I wherein the substitutents are as described herein. Further provided are methods of using such compounds for the treatment of nuclear hormone receptor-associated conditions, such as age related diseases, for example sarcopenia, and also provided are pharmaceutical compositions containing such compounds.