16177-56-3

Usage

Uses

Used in Medicinal Chemistry:
((1S,2S)-2-(aminomethyl)cyclopropyl)methanol is utilized as a building block in the synthesis of pharmaceuticals, capitalizing on its distinctive structure and functional groups to create novel therapeutic agents.
Used in Drug Design:
In drug design, ((1S,2S)-2-(aminomethyl)cyclopropyl)methanol serves as a valuable component, potentially enhancing the development of new drugs by offering a versatile template for chemical modifications.
Used in Metal-Catalyzed Reactions:
((1S,2S)-2-(aminomethyl)cyclopropyl)methanol is employed as a ligand in metal-catalyzed reactions, facilitating the synthesis of complex organic molecules with potential applications in various industries.
Used in Synthesis of Amino-Substituted Compounds:
The presence of the amino group in ((1S,2S)-2-(aminomethyl)cyclopropyl)methanol makes it a potential precursor for the synthesis of various amino-substituted compounds, which may exhibit biological activity and contribute to the advancement of pharmaceuticals and other bioactive molecules.
It is crucial to handle ((1S,2S)-2-(aminomethyl)cyclopropyl)methanol with appropriate care and adhere to safety protocols due to its potential reactivity and biological activity.

Upstream product

• 56447-11-1 2-cyano-1-cyclopropanecarboxylic acid ethyl ester 

Downstream Products

• 1360603-30-0 cis-2-(N-BOC-aminomethyl)-cyclopropanemethanol 

Relevant academic research and scientific papers

D3 RECEPTOR AGONIST COMPOUNDS; METHODS OF PREPARATION; INTERMEDIATES THEREOF; AND METHODS OF USE THEREOF

Disclosed herein are novel compounds including dopamine D3 receptor agonists, compositions thereof, methods of use thereof, and processes of synthesizing the same. Further disclosed are D3R selective agonist compounds, specifically bitopic ligands comprising chirality.

The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D3 Receptor (D3R) Selective Agonists

Because of the large degree of homology among dopamine D2-like receptors, discovering ligands capable of discriminating between the D2, D3, and D4 receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chemical modification of the D3 preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D3R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D3R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D3R binding selectivities than the reference compounds. Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation.

Purine derivatives

Purines and pyrimidines having a fused cyclopropane ring in the side chain and the heterocyclic isosteres of said purines and pyrimidines have antiviral activity, especially against viruses of the herpes class.