952747-32-9

Usage

Uses

Used in Organic Synthesis:
(R)-O-(pyrrolidin-2-ylmethyl)hydroxylamine is used as a chiral auxiliary in organic synthesis for the asymmetric synthesis of various compounds. Its chiral nature allows for the selective formation of desired enantiomers, which is crucial in the production of enantiomerically pure compounds with specific biological activities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-O-(pyrrolidin-2-ylmethyl)hydroxylamine is employed as a chiral auxiliary for the synthesis of enantiomerically pure drugs. The ability to control the stereochemistry of a reaction is essential for the development of drugs with desired therapeutic effects and reduced side effects.
Used in Transition Metal-Catalyzed Asymmetric Synthesis:
(R)-O-(pyrrolidin-2-ylmethyl)hydroxylamine also serves as a ligand in transition metal-catalyzed asymmetric synthesis reactions. Its chiral structure can be coordinated to transition metals, facilitating the enantioselective formation of complex molecules with high stereocontrol.
Used in Drug Development:
Due to its chiral nature and ability to influence the stereochemistry of reactions, (R)-O-(pyrrolidin-2-ylmethyl)hydroxylamine has potential applications in the development of new drugs and medicinal compounds. Its use in the synthesis of chiral molecules can lead to the discovery of novel therapeutic agents with improved efficacy and selectivity.

Upstream product

• 863991-04-2 2-aminooxymethyl-(S)-pyrrolidine-1-carboxylic acid t-butyl ester 
• 863991-05-3 (R)-tert-butyl 2-(aminooxymethyl)pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Novel analogues of istaroxime, a potent inhibitor of Na+,K +-ATPase: Synthesis and structure-activity relationship

We report the synthesis and biological properties of novel inhibitors of the Na+,K+-ATPase as positive inotropic compounds. Following our previously described model from which Istaroxime was generated, the 5α,14α-androstane skeleton was used as a scaffold to study the space around the basic chain of our lead compound. Some compounds demonstrated higher potencies than Istaroxime on the receptor and the (E)-3-[(R)-3- pyrrolidinyl]oxime derivative, 15, was the most potent; as further confirmation of our model, the E isomers of the oxime are more potent than the Z form. The compounds tested in the guinea pig model induced positive inotropic effects, which are correlated to the in vitro inhibitory potency on the Na +,K+-ATPase. The finding that all tested compounds resulted less proarrhythmogenic than digoxin, a currently clinically used positive inotropic agent, suggests that this could be a feature of the 3-aminoalkyloxime derivative class of 5α,14α-androstane.

AZAHETEROCYCLYL DERIVATIVES OF ANDROSTANES AND ANDROSTENES AS MEDICAMENTS FOR CARDIOVASCULAR DISORDERS

Compounds of formula (I) wherein: the groups are as defined in the description, are useful for the preparation of medicaments for the treatment of cardiovascular disorders, in particular heart failure and hypertension. The compounds are inhibitors of the enzymatic activity of the Na+,K+-ATPase. They are useful for the preparation of a medicament for the treatment of a disease caused by the hypertensive effects of endogenous ouabain, such as renal failure progression in autosomal dominant polycystic renal disease (ADPKD), preeclamptic hypertension and proteinuria and renal failure progression in patients with adducin polymorphisms.