α‐Amino boronates as cyanoborane complexes: crystal structure and inhibition properties for the serine proteases: α‐chymotrypsin and trypsin

Abstract

The first examples of α-amino boronate complexes stabilized by amino cyanoborane complexation were tested as trypsin and chymotrypsin inhibitors, and they showed moderate inhibition. The structure of compound 1 that contains two different boron atoms reveals that the geometry around the boron atom in the cyano group is tetrahedral, whereas a trigonal planar geometry exists around the boron atom attached to two oxygen atoms and a carbon atom.

Aminoboronic acids and esters: from synthetic challenges to the discovery of unique classes of enzyme inhibitors

“…155 a-Amino boronate complexes stabilized by cyanoborane complexation showed moderate inhibition against trypsin and chymotrypsin. 156…”

Alkoxyamine-cyanoborane adducts: efficient cyanoborane transfer agents

“…Organoboron derivatives are also of great interest from a biological and pharmacological point of view. 6 In this context, a-aminoboronic acids, considered as isoelectronic analogues of amino acids, have been reported as inhibitors of proteases; 7 aminocarboxyboranes, and their precursors amine-cyanoboranes 8 have shown antifungal, antibacterial, antiarthritic, and antiinflammatory properties. 9 Some cyanoboronated nucleosides have been reported to act as potent antitumor agents in mammalian cell lines, and to possess antiinflammatory and hypolipidemic activities.…”