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General Description

Trans-3,4-difluoropyrrolidine hydrochloride is a chemical compound that belongs to the class of organic compounds known as fluoroalkylamines. It is a hydrochloride salt of trans-3,4-difluoropyrrolidine, and it is commonly used in the pharmaceutical industry as a building block for the synthesis of various biologically active compounds. The presence of fluorine atoms in its structure makes it useful in medicinal chemistry for the development of fluorinated drugs. trans-3,4-difluoropyrrolidine hydrochloride has potential applications in drug discovery and development due to its unique chemical properties and potential biological activities. Additionally, its hydrochloride salt form enhances its stability and solubility, making it more suitable for various pharmaceutical formulations.

Upstream product

• 869488-97-1 (3R,4S)-rel-3,4-difluoropyrrolidine-1-carboxylic acid benzyl ester 
• 932034-24-7 (3R,4S)-3,4-Difluoro-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Urea Derivatives of 2-Aryl-benzothiazol-5-amines: A New Class of Potential Drugs for Human African Trypanosomiasis

A previous publication from this lab (Patrick, et al. Bioorg. Med. Chem. 2016, 24, 2451-2465) explored the antitrypanosomal activities of novel derivatives of 2-(2-benzamido)ethyl-4-phenylthiazole (1), which had been identified as a hit against Trypanosoma brucei, the causative agent of human African trypanosomiasis. While a number of these compounds, particularly the urea analogues, were quite potent, these molecules as a whole exhibited poor metabolic stability. The present work describes the synthesis of 65 new analogues arising from medicinal chemistry optimization at different sites on the molecule. The most promising compounds were the urea derivatives of 2-aryl-benzothiazol-5-amines. One such analogue, (S)-2-(3,4-difluorophenyl)-5-(3-fluoro-N-pyrrolidylamido)benzothiazole (57) was chosen for in vivo efficacy studies based upon in vitro activity, metabolic stability, and brain penetration. This compound attained 5/5 cures in murine models of both early and late stage human African trypanosomiasis, representing a new lead for the development of drugs to combat this neglected disease.

New fluorinated pyrrolidine and azetidine amides as dipeptidyl peptidase IV inhibitors

Cyclohexylglycine amides of various fluorinated pyrrolidines and azetidines were prepared and tested for activity against dipeptidyl peptidase IV and in vivo in the KK mouse model of type 2 diabetes. The tetrafluoropyrrolidide, cis-3,4-difluoropyrrolidide and the fluorinated azetidides displayed unexpectedly strong activity.