49763-69-1Relevant articles and documents
Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands
Dilauro, Giuseppe,Azzollini, Claudia S.,Vitale, Paola,Salomone, Antonio,Perna, Filippo M.,Capriati, Vito
supporting information, p. 10632 - 10636 (2021/04/09)
Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.
Boronic ester-linked macrocyclic lipopeptides as serine protease inhibitors targeting Escherichia coli type I signal peptidase
Sza?aj, Natalia,Lu, Lu,Benediktsdottir, Andrea,Zamaratski, Edouard,Cao, Sha,Olanders, Gustav,Hedgecock, Charles,Karlén, Anders,Erdélyi, Máté,Hughes, Diarmaid,Mowbray, Sherry L.,Brandt, Peter
supporting information, p. 1346 - 1360 (2018/09/13)
Type I signal peptidase, with its vital role in bacterial viability, is a promising but underexploited antibacterial drug target. In the light of steadily increasing rates of antimicrobial resistance, we have developed novel macrocyclic lipopeptides, linking P2 and P1′ by a boronic ester warhead, capable of inhibiting Escherichia coli type I signal peptidase (EcLepB) and exhibiting good antibacterial activity. Structural modifications of the macrocyclic ring, the peptide sequence and the lipophilic tail led us to 14 novel macrocyclic boronic esters. It could be shown that macrocyclization is well tolerated in terms of EcLepB inhibition and antibacterial activity. Among the synthesized macrocycles, potent enzyme inhibitors in the low nanomolar range (e.g. compound 42f, EcLepB IC50 = 29 nM) were identified also showing good antimicrobial activity (e.g. compound 42b, E. coli WT MIC = 16 μg/mL). The unique macrocyclic boronic esters described here were based on previously published linear lipopeptidic EcLepB inhibitors in an attempt to address cytotoxicity and hemolysis. We show herein that structural changes to the macrocyclic ring influence both the cytotoxicity and hemolytic activity suggesting that the P2 to P1’ linker provide means for optimizing off-target effects. However, for the present set of compounds we were not able to separate the antibacterial activity and cytotoxic effect.
An unsymmetrically π-extended porphyrin-based single-crystal field-effect transistor and its anisotropic carrier-transport behavior
Choi, Soojung,Chae, Seung Hyun,Hoang, Mai Ha,Kim, Kyung Hwan,Huh, Jung A,Kim, Youngmee,Kim, Sung-Jin,Choi, Dong Hoon,Lee, Suk Joong
supporting information, p. 2247 - 2251 (2013/03/28)
Anisotropic charge transport: Single-crystal organic field-effect transistor devices derived from aggregates of thiophene-appended porphyrins display very high mobility (0.27 cm2 V-1 s-1). This behavior is due to staircase stacking of the porphyrins with distances between layers of 3.17(7) A. Furthermore, the charge-transport behavior is anisotropic owing to an anisotropic molecular arrangement in the single-crystal microplates. Copyright
