374674-80-3Relevant academic research and scientific papers
Preventing Candida albicans biofilm formation using aromatic-rich piperazines
Simon, Ga?lle,Bérubé, Christopher,Paquet-C?té, Pierre-Alexandre,Grenier, Daniel,Voyer, Normand
, (2020/10/23)
The global increase in microbial resistance is an imminent threat to public health. Effective treatment of infectious diseases now requires new antimicrobial therapies. We report herein the discovery of aromatic-rich piperazines that inhibit biofilm forma
Total Synthesis of Herquline B and C
Cox, Joshua B.,Kimishima, Aoi,Wood, John L.
, p. 25 - 28 (2019/01/16)
The total syntheses of (-)-herquline B (2) and a heretofore-unrecognized congener, (+)-herquline C (3), are described. The syntheses require 14 and 13 steps, respectively, and feature a key oxazoline reduction that sets the stage for piperazine construction.
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.
Homologous NRPS-like gene clusters mediate redundant small-molecule biosynthesis in Aspergillus flavus
Forseth, Ry R.,Amaike, Saori,Schwenk, Daniel,Affeldt, Katharyn J.,Hoffmeister, Dirk,Schroeder, Frank C.,Keller, Nancy P.
supporting information, p. 1590 - 1594 (2013/04/10)
Biosynthetic crosstalk: Most gene clusters in fungi are orphans with no known associated metabolites. NMR-based comparative metabolomics was used to identify the products of two highly homologous orphan clusters in Aspergillus flavus. The two clusters enc
Total synthesis of mycocyclosin
Cochrane, James R.,White, Jonathan M.,Wille, Uta,Hutton, Craig A.
, p. 2402 - 2405 (2012/06/18)
The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura-Suzuki cross-coupling to generate the biaryl linkage.
Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus
Donkor,Sanders, M. Lee
, p. 2647 - 2649 (2007/10/03)
The reported diketopiperazine calpain inhibitor, cis-L-L-3,6-bis-(4-hydroxybenzyl)-1,4-dimethylpiperazine-2,5-dione 1, and its analogues 3 and 4 were synthesized from the corresponding amino acids. The previously assigned structure of 1 is confirmed but n
