650-16-8Relevant academic research and scientific papers
Design, Synthesis and Biological Evaluation of Highly Potent Simplified Archazolids
Rivière, Solenne,Vielmuth, Christin,Ennenbach, Christiane,Abdelrahman, Aliaa,Lemke, Carina,Gütschow, Michael,Müller, Christa E.,Menche, Dirk
supporting information, p. 1348 - 1363 (2020/06/17)
The archazolids are potent antiproliferative compounds that have recently emerged as a novel class of promising anticancer agents. Their complex macrolide structures and scarce natural supply make the development of more readily available analogues highly important. Herein, we report the design, synthesis and biological evaluation of four simplified and partially saturated archazolid derivatives. We also reveal important structure-activity relationship data as well as insights into the pharmacophore of these complex polyketides.
Total Synthesis of Archazolid F
Scheeff, Stephan,Menche, Dirk
supporting information, p. 271 - 274 (2019/01/04)
A partial bioinspired as well as the total synthesis of archazolid F, a highly potent V-ATPase inhibitory, antiproliferative polyketide macrolide, is described. Key features of the synthetic routes include a highly stereoselective aldol condensation of tw
Polyfluoroalkoxy phosphonic and phosphinic acid derivatives: II. Reversible esterase inhibitors
Krutikova,Krutikov,Erkin
scheme or table, p. 434 - 439 (2010/08/04)
Polyfluoroalkyl esters of phosphoric, alkylphosphonic and 1-hydroxypolyfluoroalkylphosphonic acids exhibited significant antiesterase activity against various esterases of animal and microbial origin. Moreover, with some compounds reversible inhibition of enzymes was observed due to the specific influence of hydrophobic fragments of the target products.
A practical synthesis of the ansa chain of benzenic ansamycin antibiotics: Total synthesis of an ansatrienol derivative
Kashin, Dmitry,Meyer, Axel,Wittenberg, Ruediger,Schoening, Kai-Uwe,Kamlage, Stefan,Kirschning, Andreas
, p. 304 - 319 (2007/10/03)
A practical and stereocontrolled synthetic approach towards the ansa chain of the benzenic ansamycins (mycotrienins) is described, which can be scaled up to multigram quantities. Key features of the synthesis are the formation of the Z-configured tri-subs
Fluorinated phosphorus compounds: Part 2. The synthesis of some bis(fluoroalkyl) alkylphosphonates
Timperley, Christopher M.,Broderick, John F.,Holden, Ian,Morton, Ian J.,Waters, Matthew J.
, p. 43 - 52 (2007/10/03)
Twenty bis(fluoroalkyl) alkylphosphonates of structure (RFO)2P(O)R were prepared in 28-69% yields by treatment of alkylphosphonic dichlorides Cl2P(O)R [R=Me, Et, n-Pr, i-Pr] with fluoroalcohols RFOH [RF=CF3CH2, H(CF2)2CH2, C2F5CH2, C3H7CH2, (CF3)2CH] in diethyl ether in the presence of triethylamine. Reactions of isopropylphosphonic dichloride with two molar equivalents of alcohols and fluoroalcohols were compared. After 12h at room temperature, the alcohols EtOH, n-PrOH, i-PrOH and n-BuOH gave mixtures of monoesters and diesters, except isopropanol, which gave the monoester exclusively. Electronic and steric effects caused by the alkoxy substituents satisfactorily account for the product ratios. With the fluoroalcohols CF3CH2OH, C2F5CH2OH, C3F7CH2OH and (CF3)2CHOH, the diesters predominated. Here the electronic effects of the fluoroalkoxy substituents stabilise the intermediate phosphoranes, eg. Cl2(RFO)P(OH)i-Pr and Cl(RFO)2P(OH)i-Pr, and drive the reactions to completion. Steric effects are clearly much less important in the case of attack by fluorinated alcohols.
A convenient method for the synthesis of bis-trifluoroethyl phosphonoacetates
Patois,Savignac,About-Jaudet,Collignon
, p. 2391 - 2396 (2007/10/02)
Bis-trifluoroethyl phosphonoacetates were easily obtained by condensation of bis-trifluoroethyl alkylphosphonates with alkyl chloroformates in the presence of 2 equivalents of lithium hexamethyldisilazane (LiHMDS).
