3354-31-2Relevant articles and documents
Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C
Takahashi, Shu,Kimishima, Aoi,Hirose, Tomoyasu,Yamada, Takeshi,Sugawara, Akihiro,Shirahata, Tatsuya,Noguchi, Yoshihiko,Iwatsuki, Masato,Hokari, Rei,Ishiyama, Aki,Kobayashi, Yoshinori,Sunazuka, Toshiaki
, (2021/02/20)
The concise enantioselective total synthesis of Diatretol (1) has been achieved via 9 steps with 30％ yield. The synthetic approach involves stereoselective oxidation and regioselective transacetalization utilizing a folded conformation induced by an intramolecular CH/π interaction. In addition, we have also achieved total synthesis of three diketopiperazine natural products, Lepistamides A (2), B (3) and C (4).
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
Simon, Ga?lle,Bérubé, Christopher,Voyer, Normand,Grenier, Daniel
, p. 2323 - 2331 (2018/12/11)
Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure–activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.
Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities
Bérubé, Christopher,Cardinal, Sébastien,Boudreault, Pierre-Luc,Barbeau, Xavier,Delcey, Nicolas,Giguère, Martin,Gleeton, Dave,Voyer, Normand
, p. 8077 - 8084 (2015/12/30)
With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands.
