Sila‐Pharmaka, 37¹⁾ Darstellung und Eigenschaften der Enantiomere der Antimuskarinika Sila‐Procyclidin und Sila‐Tricyclamol‐iodid: Optisch aktive Silanole mit Silicium als Chiralitätszentrum²⁾

Serine Protease Inhibition by a Silanediol Peptidomimetic

“…13 A covalent interaction between the silicon and the enzyme would contrast with previously described silanediol inhibitors that have been inhibitors of aspartic and metallo proteases where water is the nucleophilic group. 14,15 …”

“…Silanols have potential as serine protease inhibitors because a silanol hydroxyl will rapidly exchange with water and with alcohols (Scheme ) . A covalent interaction between the silicon and the enzyme would contrast with previously described silanediol inhibitors that have been inhibitors of aspartic and metallo proteases where water is the nucleophilic group. , …”

Chemistry of Silicon‐Containing Amino Acids

“…The exceptional strength of the SiÀO bond (512 kJ/mol for Me 3 SiÀOMe) makes silanols and silyl ethers intrinsically stable [5], but these are also very easily exchanged with solvent. Enantiomercially pure trialkylsilanols racemize rapidly in aqueous solvents [7]. …”

Silanediol Protease Inhibitors: From Conception to Validation

“…An example of this approach is the conversion of the histamine antagonist terfenadine ( 4a ) to sila‐terfenadine ( 4b ), yielding an effective and novel drug candidate 14. Similarly, replacing the carbinol of the muscarinic receptor agonist 5a with a silanol gave 5b with superior agonist properties 15. Currently the two organosilanes produced industrially for their biological activity are the antifungal flusilazole ( 6 )16 and the pyrethroid insecticide silafluofen ( 7 ),17 both agricultural chemicals and examples of the “silicon‐for‐carbon switch” approach.…”