16165-66-5Relevant articles and documents
Phosphonate inhibitors of antigen 85C, a crucial enzyme involved in the biosynthesis of the Mycobacterium tuberculosis cell wall
Gobec, Stanislav,Plantan, Ivan,Mravljak, Janez,Wilson, Rosalind A.,Besra, Gurdyal S.,Kikelj, Danijel
, p. 3559 - 3562 (2004)
The first phosphonate inhibitors of antigen 85C - a major protein component of the Mycobacterium tuberculosis cell wall possessing mycolyltransferase activity were prepared using structure-based design. These potential novel antituberculosis agents, consisting of a phosphonate moiety, hydrophobic alkyl chain and a simple trehalose-mimicking aromatic structure, were designed as tetrahedral transition-state analogue inhibitors of antigen 85C, which catalyzes the key mycolyltransferase reaction involved in cell wall biosynthesis.
Conjugate Addition of Alkyl- and Vinyl-copper Complexes to α,β-Unsaturated Phosphonic Esters. Stereospecific Syntheses of γ,δ-Unsaturated Phosphonates
Nicotra, Francesco,Panza, Luigi,Russo, Giovanni
, p. 5 - 6 (1984)
Alkylcopper complexes add to diethyl ethenylphosphonate to afford phosphonic esters with the alkyl chain increased by two carbon atoms; analogously vinylcopper complexes afford γ,δ-unsaturated phosphonic esters with retention of configuration in the double bond.
Selective esterification of phosphonic acids
Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
, (2021/09/27)
Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.
Organic Compounds
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Page/Page column 7, (2010/05/13)
Disclosed are compounds having the ability to inhibit cytochrome P450 2A6, 2A13, and/or 2B6 and tobacco products comprising them. Also disclosed are pharmaceutical compositions comprising them.
