76280-61-0Relevant articles and documents
Stereoselective Synthesis of Baulamycin A
Sherman, David H.,Thielman, Jonathan R.,Williams, Robert M.
, p. 3812 - 3823 (2020/03/23)
New structural classes of antibiotics are rare, structurally novel broad-spectrum antibiotics exceptionally so. The recently discovered baulamycins constitute a remarkable example of these highly prized compounds and, as such, have attracted considerable attention in the form of both synthetic efforts and biological studies. For the first time, we report a gram-scale preparation of the common carbon framework of the baulamycin family, as well as the total synthesis of its most potent member, baulamycin A. Our approach employs highly stereoselective, catalyst-controlled asymmetric conjugate additions to thioesters to set key stereocenters, as well as the first reported use of "dry ozonolysis" to reveal a masked carboxylic acid in the total synthesis of a natural product.
Structural Revision of Baulamycin A and Structure-Activity Relationships of Baulamycin A Derivatives
Sengupta, Sandip,Bae, Munhyung,Oh, Dong-Chan,Dash, Uttam,Kim, Hak Joong,Song, Woon Young,Shin, Injae,Sim, Taebo
, p. 12947 - 12966 (2017/12/26)
Total synthesis of the proposed structure of baulamycin A was performed. The spectral properties of the synthetic compound differ from those reported for the natural product. On the basis of comprehensive NMR study, we proposed two other possible structur
New multi-target-directed small molecules against Alzheimer's disease: A combination of resveratrol and clioquinol
Mao, Fei,Yan, Jun,Li, Jianheng,Jia, Xian,Miao, Hui,Sun, Yang,Huang, Ling,Li, Xingshu
, p. 5936 - 5944 (2014/08/05)
Alzheimer's disease (AD) is currently one of the most difficult and challenging diseases to treat. Based on the 'multi-target-directed ligands' (MTDLs) strategy, we designed and synthesised a series of new compounds against AD by combining the pharmacophores of resveratrol and clioquinol. The results of biological activity tests showed that the hybrids exhibited excellent MTDL properties: a significant ability to inhibit self-induced β-amyloid (Aβ) aggregation and copper(ii)-induced Aβ aggregation, potential antioxidant behaviour (ORAC-FL value of 0.9-3.2 Trolox equivalents) and biometal chelation. Among these compounds, (E)-5-(4-hydroxystyryl)quinoline-8-ol (10c) showed the most potent ability to inhibit self-induced Aβ aggregation (IC50 = 8.50 μM) and copper(ii)-induced Aβ aggregation and to disassemble the well-structured Aβ fibrils generated by self- and copper(ii)-induced Aβ aggregation. Note that 10c could also control Cu(i/ii)-triggered hydroxyl radical (OH) production by halting copper redox cycling via metal complexation, as confirmed by a Cu-ascorbate redox system assay. Importantly, 10c did not show acute toxicity in mice at doses of up to 2000 mg kg-1 and was able to cross the blood-brain barrier (BBB), according to a parallel artificial membrane permeation assay. These results indicate that compound 10c is a promising multifunctional compound for the development of novel drugs for AD. This journal is the Partner Organisations 2014.