Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C

• Karolina Wątroba,
• Małgorzata Pawełczak and
• Marcin Kaźmierczak

Beilstein J. Org. Chem. 2023, 19, 434–439, doi:10.3762/bjoc.19.33

• Poznań, Uniwersytetu Poznańskiego 10, 61-614 Poznań, Poland 10.3762/bjoc.19.33 Abstract In this paper, we present the solvolysis reaction of dipeptide analogues of fluorinated aminophosphonates with simultaneous quantitative deprotection of the amino group. To the best of our knowledge, this work is the

• first reported example of the application of fluorinated aminophosphonates in cathepsin C inhibition studies. The new molecules show moderate inhibition of the cathepsin C enzyme, which opens the door to consider them as potential therapeutic agents. Overall, our findings provide a new avenue for the

• fluorinated aminophosphonates [23][24] with the simultaneous deprotection of the amino group. The free amines were subjected to kinetic studies to investigate their interaction with cathepsin C. The required steps should be simple and fast, and the conditions of the reactions should be as mild as possible

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• that was proposed based on NMR studies. Keywords: dipeptide analogues; fluorinated aminophosphonates; fluorine; nucleophilic fluorination; phosphorus; Introduction The chemistry of fluorinated aminophosphonates is constantly being developed, mainly due to their wide spectra of applications. What is

• more, they are valuable targets for biomedical investigations. Due to the strong interest in this type of compounds, several marvelous reviews about the synthesis and application of fluorinated aminophosphonates have been published in recent years [1][2][3]. To the best of our knowledge, among the many

• applications of fluorinated aminophosphonates and aminophosphonic acid derivatives, they exhibit antiviral [4][5], antibacterial [6] and antifungal [7] activities. Moreover, α-fluorinated phosphonates can be considered as hydrolytically stable mimics of naturally occurring phosphates [8]. Due to the fact that

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

• Natalia V. Pavlenko,
• Tatiana I. Oos,
• Yurii L. Yagupolskii,
• Igor I. Gerus,
• Uwe Doeller and
• Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

• of its strong electronegativity. This enables modulation of the lipophilicity profile, of electrostatic interactions with the target structure and inhibition of some metabolic pathways [7][8][9]. Data concerning the biological activity and synthetic approaches toward fluorinated aminophosphonates