184366-20-9Relevant academic research and scientific papers
Synthesis, antimycobacterial activity and influence on mycobacterial InhA and PknB of 12-membered cyclodepsipeptides
Laqua, Katja,Klemm, Marcel,Richard-Greenblatt, Melissa,Richter, Adrian,Liebe, Linda,Huang, Tingting,Lin, Shuangjun,Guardia, Ana,Pérez-Herran, Esther,Ballell, Lluís,Av-Gay, Yossef,Imming, Peter
, p. 3166 - 3190 (2018/05/05)
In recent years, several small natural cyclopeptides and cyclodepsipeptides were reported to have antimycobacterial activity. Following this lead, a synthetic pathway was developed for a small series of 12-membered ring compounds with one amide and two ester bonds (cyclotridepsipeptides). Within the series, the ring system proved to be necessary for growth inhibition of Mycobacterium smegmatis and Mycobacterium tuberculosis in the low micromolar range. Open-chain precursors and analogues were inactive. The compounds modulated autophosphorylation of the mycobacterial protein kinase B (PknB). PknB inhibitors were active at μM concentration against mycobacteria while inducers were inactive. PknB regulates the activity of the mycobacterial reductase InhA, the target of isoniazid. The activity of the series against Mycobacterium bovis BCG InhA overexpressing strains was indistinguishable from that of the parental strain suggesting that they do not inhibit InhA. All substances were not cytotoxic (HeLa > 5 μg/ml) and did not show any significant antiproliferative effect (HUVEC > 5 μg/ml; K-562 > 5 μg/ml). Within the scope of this study, the molecular target of this new type of small cyclodepsipeptide was not identified, but the data suggest interaction with PknB or other kinases may partly cause the activity.
Benzylation of nitroalkanes using copper-catalyzed thermal redox catalysis: Toward the facile C-alkylation of nitroalkanes
Gildner, Peter G.,Gietter, Amber A. S.,Cui, Di,Watson, Donald A.
supporting information; experimental part, p. 9942 - 9945 (2012/08/07)
The C-alkylation of nitroalkanes under mild conditions has been a significant challenge in organic synthesis for more than a century. Herein we report a simple Cu(I) catalyst, generated in situ, that is highly effective for C-benzylation of nitroalkanes using abundant benzyl bromides and related heteroaromatic compounds. This process, which we believe proceeds via a thermal redox mechanism, allows access to a variety of complex nitroalkanes under mild reaction conditions and represents the first step toward the development of a general catalytic system for the alkylation of nitroalkanes.
Azepine derivatives useful as nitric oxide synthase inhibitors
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, (2008/06/13)
The current invention discloses azepine derivatives useful as nitric oxide synthase inhibitors.
2-Iminopyrrolidines as potent and selective inhibitors of human inducible nitric oxide synthase
Hagen, Timothy J.,Bergmanis, Arija A.,Kramer, Steven W.,Fok, Kam F.,Schmelzer, Albert E.,Pitzele, Barnett S.,Swenton, Lydia,Jerome, Gina M.,Kornmeier, Christine M.,Moore, William M.,Branson, Linda F.,Connor, Jane R.,Manning, Pamela T.,Currie, Mark G.,Hallinan, E. Ann
, p. 3675 - 3683 (2007/10/03)
A series of substituted 2-iminopyrrolidines has been prepared and shown to be potent and selective inhibitors of the human inducible nitric oxide synthase (hiNOS) isoform versus the human endothelial nitric oxide synthase (heNOS) and the human neuronal ni
