213698-56-7Relevant academic research and scientific papers
Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis
Noble, Adam,Roesner, Stefan,Aggarwal, Varinder K.
, p. 15920 - 15924 (2016/12/16)
Short and highly stereoselective total syntheses of the sesquilignan natural product tatanan A and its C3 epimer are described. An assembly-line synthesis approach, using iterative lithiation–borylation reactions, was applied to install the three contiguo
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents
Wang, Guangcheng,Wang, Fang,Cao, Dong,Liu, Yibin,Zhang, Ronghong,Ye, Haoyu,Li, Xiuxia,He, Lin,Yang, Zhuang,Ma, Liang,Peng, Aihua,Xiang, Mingli,Wei, Yuquan,Chen, Lijuan
, p. 3158 - 3163 (2014/06/24)
A series of barbigerone analogues (7a-7w, 13a-13x) were designed, synthesized and biologically evaluated for their anti-proliferative and anti-angiogenic activities. Among these compounds, compound 13a exhibited the most potent inhibitory effect on the proliferation of HUVECs, HepG2, A375, U251, B16, and HCT116 cells (IC50 = 3.80, 0.28, 1.58, 3.50, 1.09 and 0.68 μM, respectively). Compound 13a inhibited the angiogenesis in zebrafish embryo assay in a concentration-dependent manner. Furthermore, 13a also effectively inhibited the migration and capillary like tube formation of human umbilical vein endothelial cell in vitro. These results support the further investigation of this class of compounds as potential anti-proliferative and anti-angiogenesis agents.
Studies toward the development of antiproliferative neoclerodanes from salvinorin A
Vasiljevik, Tamara,Groer, Chad E.,Lehner, Kurt,Navarro, Hernan,Prisinzano, Thomas E.
, p. 1817 - 1824 (2014/11/07)
The success rate for central nervous system (CNS) drug candidates in the clinic is relatively low compared to the industry average across other therapeutic areas. Penetration through the blood-brain barrier (BBB) to reach the therapeutic target is a major obstacle in development. The rapid CNS penetration of salvinorin A has suggested that the neoclerodane nucleus offers an excellent scaffold for developing antiproliferative compounds that enter the CNS. The Liebeskind-Srogl reaction was used as the main carbon-carbon bond-forming step toward the synthesis of quinone-containing salvinorin A analogues. Quinone-containing salvinorin A analogues were shown to have antiproliferative activity against the MCF7 breast cancer cell line, but show no significant activity at the κ-opioid receptors. In an in vitro model of BBB penetration, quinone-containing salvinorin A analogues were shown to passively diffuse across the cell monolayer. The analogues, however, are substrates of P-glycoprotein, and thus further modification of the molecules is needed to reduce the affinity for the efflux transporter.
Synthesis of macrocyclic ketones exploiting palladium-catalyzed activation of carboxylic acids as an enabling step
Kapdi, Anant R.,Fairlamb, Ian J. S.
, p. 961 - 964 (2013/06/27)
The novel synthesis of macrocyclic arylketones via palladium-catalyzed cross-coupling of arylboronic acids and carboxylic acids, activated by the treatment with di(N-succinimidyl) carbonate, is disclosed. This allows the high yielding synthesis of various
Simple palladium(II) precatalyst for suzuki-miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners
Burns, Michael J.,Fairlamb, Ian J. S.,Kapdi, Anant R.,Sehnal, Petr,Taylor, Richard J. K.
, p. 5397 - 5400 (2008/09/17)
trans-PdBr(N-Succ)(PPh3)2 (1) is a universally effective precatalyst for Suzuki-Miyaura cross-couplings of benzylic halides with aryl- or heteroarylboronic acids. Substituted aryl halides and halogenated cyclic enones can be cross-coupled with aryl- or vinylboronic acids in excellent yields. Catalyst recycling is also demonstrated.
