76280-60-9Relevant 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.
A systematic study of peripherally multiple aromatic ester-functionalized poly(benzyl ether) dendrons for the fabrication of organogels: Structure-property relationships and thixotropic property
Feng, Yu,Liu, Zhi-Xiong,Chen, Hui,Yan, Zhi-Chao,He, Yan-Mei,Liu, Chen-Yang,Fan, Qing-Hua
, p. 7069 - 7082 (2014/06/09)
A new class of peripherally multiple aromatic ester-functionalized poly(benzyl ether) dendrons and/or dendrimers with different focal point substituents, surface groups, interior structures, as well as different generations have been synthesized and their structure-property relationships with respect to their gelation ability have been investigated systematically. Most of these dendrons are able to gel organic solvents over a wide polarity range. Evident dendritic effects were observed not only in gelation capability but also in thermotropic, morphological, and rheological characterizations. It was disclosed that subtle changes in peripheral ester functionalities and interior dendritic structures affected the gelation behavior of the dendrons significantly. Among all the dendrons studied, the second- and third-generation dendrons G0G2-Me and G0G3-Me with dimethyl isophthalates (DMIP) as peripheral groups exhibited the best capability in gelation, and stable gels were formed in more than 22 aromatic and polar organic solvents. The lowest critical gelation concentration (CGC) reached 2.0 mg mL-1, indicating that approximately 1.35×104 solvent molecules could be entrapped by one dendritic molecule. Further study on driving forces in gel formation was carried out by using a combination of single-crystal/powder X-ray diffraction (XRD) analysis and concentration- dependent (CD)/temperature-dependent (TD) 1H NMR spectroscopy. The results obtained from these experiments revealed that the multiple π-π stacking of extended π-systems due to the peripheral DMIP rings, cooperatively assisted by non-conventional hydrogen-bonding, is the key contributor in the formation of the highly ordered supramolecular and fibrillar network. In addition, these dendritic organogels exhibited unexpected thixotropic-responsive properties, which make them promising candidates with potential applications in the field of intelligent soft materials. s
Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes
Schmidt, Bernd,Elizarov, Nelli,Berger, René,H?lter, Frank
, p. 3674 - 3691 (2013/06/27)
4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.
Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives
Kim, Taejung,Lee, Woojung,Jeong, Kyu Hyuk,Song, Jung Ho,Park, Soon-Hye,Choi, Pilju,Kim, Su-Nam,Lee, Seokjoon,Ham, Jungyeob
, p. 4122 - 4126 (2012/07/03)
Amorphastilbol (APH-1), isolated from a Robinia pseudoacacia var. umbraculifer seed extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki-Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2-APH-12 for PPAR agonist activity. APH-4 and APH-11 were effective PPARα/γ transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARα/γ agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.
TRISUBSTITUTED BORON-CONTAINING MOLECULES
-
, (2011/02/24)
This invention largely relates to 3,4,6-trisubstituted benzoxaborole compounds, and their use for treating bacterial infections.
Efficient and general preparation of pyranostilbenes: First total synthesis of artocarbene and pawhuskin B
Byung, Ho Park,Yong, Rok Lee,Won, Seok Lyoo
experimental part, p. 2146 - 2154 (2010/02/28)
An efficient and general synthesis providing pyranostilbenes in moderate yields has been developed. It consists of the reaction of pinosylvin with the appropriate a,β-unsaturated aldehyde catalyzed by ethylenediamine diacetate. As an application of this m
Total synthesis of (+)-machaeriols B and C and of their enantiomers with a cannabinoid structure
Hee, Jin Lee,Yong, Rok Lee,Sung, Hong Kim
experimental part, p. 1404 - 1412 (2009/10/17)
An efficient and concise synthesis of the biologically interesting (+)-machaeriol B (2) and its enantiomer 5 was accomplished from O-phenylhydroxylamine (7) in four steps (Scheme 2). In addition, the first total synthesis of natural (+)-machaeriol C (3) a
HSP90 FAMILY PROTEIN INHIBITORS
-
Page/Page column 28, (2010/11/28)
The present invention provides Hsp90 family protein inhibitors comprising, as an active ingredient, a benzoic acid derivative represented by General Formula (I): [wherein n represents an integer of 0 to 10; R1 represents substituted or unsubsti