4492-51-7

Usage

Uses

Used in Pharmaceutical Industry:
1-cyclopentyl-N-methyl-methanamine is used as a building block for the synthesis of various pharmaceuticals due to its potential anti-inflammatory and anti-nociceptive properties. It serves as a promising candidate for the development of therapeutic agents.
Used in Agrochemical Industry:
1-cyclopentyl-N-methyl-methanamine is also used as a building block in the synthesis of agrochemicals, contributing to the development of effective and targeted agricultural products.
Used in Asymmetric Synthesis:
1-cyclopentyl-N-methyl-methanamine is used as a chiral auxiliary in asymmetric synthesis, a technique that allows for the selective production of one enantiomer of a chiral compound, which is crucial in the creation of enantiomerically pure compounds for various applications.

InChI:InChI=1/C7H15N/c1-8-6-7-4-2-3-5-7/h7-8H,2-6H2,1H3

Upstream product

• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 4492-50-6 N-methylcyclopentanecarboxamide 
• 3637-61-4 1-amino-cyclopentanemethanol 
• 73017-76-2 methanesulfonic acid cyclopentylmethyl ester 
• 74-89-5 methylamine 

Downstream Products

• 52317-65-4 3-(4-Chloro-2-methyl-phenyl)-1-cyclopentylmethyl-1-methyl-thiourea 

Relevant academic research and scientific papers

Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides

First introduced into medicines in the 1930s, the sulfonamide functional group continues to be present in a wide range of contemporary pharmaceuticals and agrochemicals. Despite their popularity in the design of modern bioactive molecules, the underpinning methods for sulfonamide synthesis are essentially unchanged since their introduction, and rely on the use of starting materials with preinstalled sulfur-functionality. Herein we report a direct single-step synthesis of sulfonamides that combines two of the largest monomer sets available in discovery chemistry, (hetero)aryl boronic acids and amines, along with sulfur dioxide, using a Cu(II) catalyst, to deliver a broad range of sulfonamides. Sulfur dioxide is provided by the surrogate reagent DABSO. The reaction tolerates broad variation in both coupling partners, including aryl, heteroaryl and alkenyl boronic acids, as well as cyclic and acyclic alkyl secondary amines, and primary anilines. We validate the method by showing that a variety of drugs, and drug-fragments, can be incorporated into the process.

Conformational Aspects in the Design of Inhibitors for Serine Hydroxymethyltransferase (SHMT): Biphenyl, Aryl Sulfonamide, and Aryl Sulfone Motifs

Malaria remains a major threat to mankind due to the perpetual emergence of resistance against marketed drugs. Twenty-one pyrazolopyran-based inhibitors bearing terminal biphenyl, aryl sulfonamide, or aryl sulfone motifs were synthesized and tested towards serine hydroxymethyltransferase (SHMT), a key enzyme of the folate cycle. The best ligands inhibited Plasmodium falciparum (Pf) and Arabidopsis thaliana (At) SHMT in target, as well as PfNF54 strains in cell-based assays in the low nanomolar range (18–56 nm). Seven co-crystal structures with P. vivax (Pv) SHMT were solved at 2.2–2.6 ? resolution. We observed an unprecedented influence of the torsion angle of ortho-substituted biphenyl moieties on cell-based efficacy. The peculiar lipophilic character of the sulfonyl moiety was highlighted in the complexes with aryl sulfonamide analogues, which bind in their preferred staggered orientation. The results are discussed within the context of conformational preferences in the ligands.