816462-34-7Relevant academic research and scientific papers
A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine
Tian, Guilong,Song, Liangliang,Li, Zhenghua,Robeyns, Koen,Van Meervelt, Luc,Van Der Eycken, Erik V.
supporting information, p. 8441 - 8445 (2020/11/03)
A concise and flexible procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope and good functional group tolerance. The total synthesis of (±)-seco-antofine and (±)-septicine were realized employing this strategy.
Synthesis, and cyclization to aurones and flavones, of alkoxy-substituted aryl, arylalkynyl ketones
Kerr, Penelope J.,Pyke, Simon M.,Ward, A. David
, p. 350 - 358 (2008/09/19)
Acylation of 1,3,5-tribenzyloxybenzene with alkoxy-substituted phenylpropioloyl chlorides provides the corresponding aryl alkoxylarylalkynyl ketones in which one of the benzyl groups has been removed. Cyclization of these phenolic ketones using basic reagents (potassium carbonate in acetone is best) provides the corresponding aurone system. When the phenolic group of the alkynyl ketones is protected as the t-butyldimethylsilyl ether followed by cyclization, using 18-crown-6 and potassium fluoride, mixtures of the corresponding aurones and flavones are produced. A by-product from the formation of the ketones is the corresponding β-chlorochalcone, which can also be cyclized to an aurone product using basic conditions. Similarly, the t-butyldimethylsilyl ethers of the HCl adducts can also be cyclized to a mixture of the corresponding aurones and flavones. CSIRO 2008.
An efficient synthesis of neoflavonoid antioxidants based on Montmorillonite K-10 catalysis
Lee,Tseng,Lee
, p. 2247 - 2254 (2007/10/03)
A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.
Studies on disease-modifying antirheumatic drugs. III. Bone resorption inhibitory effects of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4- triazol-1-ylmethyl)quinoline-3-carboxylate (TAK-603) and related compounds
Baba, Atsuo,Oda, Tsuneo,Taketomi, Shigehisa,Notoya, Kohei,Nishimura, Atsushi,Makino, Haruhiko,Sohda, Takashi
, p. 369 - 374 (2007/10/03)
In the course of our studies aimed at obtaining new drugs for treatment of bone and joint diseases, chemical modification of the potent bone resorption inhibitors justicidins, was performed and various naphthalene lactones, quinoline lactones and quinoline derivatives bearing an azole moiety at the side chain were prepared. Their inhibitory effects on bone resorption were evaluated by Raisz's method, and several compounds, including ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4-triazol-1- ylmethyl)quinoline-3-arboxylate (6c, TAK-603), were found to have activities comparable with or superior to the justicidins. The 4-(3-isopropoxy-4- methoxy)phenyl derivative (6d), in particular, displayed a marked increase in potency. TAK-603 and compound 6d were very effective in preventing osteoclast formation and bone resorption by mature osteoelasts. Further, TAK-603 was shown to be effective in preventing bone loss in ovariectomized mice.
Synthesis of Amido-ureas and the Nature of Caracasanamide, the Hypotensive Principle of Verbesina caracasana
Crombie, Leslie,Jarrett, Sandra R. M.
, p. 3179 - 3184 (2007/10/02)
Syntheses of the (E)-1 and (Z)-2 forms of 1-(3-methylbut-2-enyl)-3-(4-butyl)urea, proposed structures for the natural hypotensive caracasanamide, have been carried out.The compounds were found not to be identical wit
