114566-93-7Relevant articles and documents
Dihydropyrrolones as bacterial quorum sensing inhibitors
Almohaywi, Basmah,Yu, Tsz Tin,Iskander, George,Chan, Daniel S.H.,Ho, Kitty K.K.,Rice, Scott,Black, David StC.,Griffith, Renate,Kumar, Naresh
, p. 1054 - 1059 (2019/03/13)
Bacteria regulate their pathogenicity and biofilm formation through quorum sensing (QS), which is an intercellular communication system mediated by the binding of signaling molecules to QS receptors such as LasR. In this study, a range of dihydropyrrolone (DHP) analogues were synthesized via the lactone-lactam conversion of lactone intermediates. The synthesized compounds were tested for their ability to inhibit QS, biofilm formation and bacterial growth of Pseudomonas aeruginosa. The compounds were also docked into a LasR crystal structure to rationalize the observed structure-activity relationships. The most active compound identified in this study was compound 9i, which showed 63.1% QS inhibition of at 31.25 μM and 60% biofilm reduction at 250 μM with only moderate toxicity towards bacterial cell growth.
Iron-catalyzed aerobic C-H functionalization of pyrrolones
Liu, Li-Wei,Wang, Zhen-Zhen,Zhang, Hui-Hui,Wang, Wan-Shu,Zhang, Ji-Zong,Tang, Yu
, p. 9531 - 9534 (2015/06/08)
The aerobic oxidation of pyrrolones catalyzed by Fe(OTf)3 to form reactive N-acyliminium ion intermediates that undergo nucleophilic additions with alcohols to give the corresponding products in moderate to good yields is described.
Enantioselective synthesis of (R)-(-)-baclofen via Ru(II)-BINAP catalyzed asymmetric hydrogenation
Thakur, Vinay V.,Nikalje, Milind D.,Sudalai
, p. 581 - 586 (2007/10/03)
A short and efficient enantioselective synthesis of (R)-(-)-baclofen, a selective GABAB agonist has been described with an overall yield of 26% and 90% ee. Ru(II)-(S)-BINAP catalyzed asymmetric hydrogenations of C=C and C=O groups constitute the key steps in introducing stereogenic centers into the molecule.