- STUDIES DIRECTED TOWARD THE PREPARATION OF POLYENE MACROLIDE MIMICS
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Cyclodimerization of two symmetrical but dissimilar fragments provides a facile route to macrocyclic dilactones containing conjugated polyolefins.Methods have been developed for the stereoselective synthesis of cis-2,4,6-triacetoxyheptanedial and the simple acylation of alcohols with dimethyl phosphonoacetic acid.
- Floyd, David M.,Fritz, Alan W.
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- Synthesis of fluorescent probes directed to the active site gorge of acetylcholinesterase
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Six organophosphorus compounds linked to fluorophore groups were prepared in an effort to selectively modify the active site of acetylcholinesterase and deliver probes to the gorge region. Two compounds that vary by the length of a methylene (CH2) group, pyrene-SO2NH(CH2)(n)NHC(O)CH2CH2P(O)(OEt)(F) (where n = 2 or 3) were found to be potent, irreversible inhibitors of recombinant mouse AChE (K(i)?105 M-1 min-1). Size exclusion chromatography afforded a fluorescently-labeled cholinesterase conjugate. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Saltmarsh, Jennifer R.,Boyd, Aileen E.,Rodriguez, Oscar P.,Radic, Zoran,Taylor, Palmer,Thompson, Charles M.
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- Synthesis of the C1-C11 western fragment of madeirolide A
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The stereocontrolled synthesis of a fully elaborated C1-11 subunit of madeirolide A is described, utilizing an asymmetric boron aldol reaction and a cis-selective hetero-Michael cyclization to form the tetrahydropyran ring, followed by efficient formation of the required C5 α-glycoside.
- Paterson, Ian,Haslett, Gregory W.
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supporting information
p. 1338 - 1341
(2013/05/09)
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- Phosphonate terminated PPH dendrimers: Influence of pendant alkyl chains on the in vitro anti-HIV-1 properties
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The synthesis, characterization and in vitro anti-HIV activity of a series of generation one dendrimers having phosphonate groups with pendant alkyl chains are described. The influence of the lateral alkyl chains on the biological properties was correlate
- Perez-Anes, Alexandra,Spataro, Gregory,Coppel, Yannick,Moog, Christiane,Blanzat, Muriel,Turrin, Cedric-Olivier,Caminade, Anne-Marie,Rico-Lattes, Isabelle,Majoral, Jean-Pierre
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experimental part
p. 3491 - 3498
(2010/01/06)
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- An efficient preparation of β-aryl-β-ketophosphonates by the TFAA/H3PO4-mediated acylation of arenes with phosphonoacetic acids
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(Chemical Equation Presented) β-Aryl-β-ketophosphonates can be efficiently prepared in good yield by using a TFAA/85% H3PO 4-mediated acylation of electron-rich arenes with phosphonoacetic acids. The conditions offer advantages over
- Luke, George P.,Seekamp, Christopher K.,Wang, Zhe-Qing,Chenard, Bertrand L.
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p. 6397 - 6400
(2008/12/21)
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- A convenient method for the preparation of chiral phosphonoacetamides and their Horner-Wadsworth-Emmons reaction
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Chiral phosphonoacetamides bearing (S)-(α-methylbenzyl)benzylamine, (S,S)-bis(α-methylbenzyl)amine, l-phenylglycine methyl ester and l-phenylglycinol were easily prepared in good yield by means of the Michaelis-Arbuzov reaction of chiral bromoacetamides obtained in quantitative yield, with trimethyl phosphite, which under Horner-Wadsworth-Emmons conditions with several aryl and alkyl aldehydes under Masamune-Roush procedure using LiCl and DBU in THF or toluene gave the corresponding chiral α,β-unsaturated amides. The present procedure is a convenient and efficient methodology for the preparation of phosphonoacetamides and chiral α,β-unsaturated amides in high E-selectivity.
- Ordonez, Mario,Hernandez-Fernandez, Eugenio,Montiel-Perez, Martin,Bautista, Rafael,Bustos, Paola,Rojas-Cabrera, Haydee,Fernandez-Zertuche, Mario,Garcia-Barradas, Oscar
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p. 2427 - 2436
(2008/03/13)
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- Reactions of trialkyl phosphites with mono- and diacylals of halo-substituted acetic acids
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Trialkyl phosphites react with diacylals of di- and trichloroacetic acids by the pathway of the Perkow reaction; with monoacylals of bromo- and iodoacetic acids, by the pathway of the classical Arbuzov reaction; and with monoacylals of di- and trichloroacetic acids, by the pathway of the nonclassical Arbuzov reaction.
- Gazizov,Gaisin,Khairullin,Safina,Karimova,Petrova
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p. 1738 - 1741
(2007/10/03)
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- Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-D-glyceric acid (1,3-diPG) analogues
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Various phosphono-phosphates and diphophonates were synthesized as 1,3-diphosphoglycerate 1,3-diPG) analogues by using a β-ketophosphonate, an α-fluoro,β-ketophosphonate or a β-ketophosphoramidate to mimic the unstable carboxyphosphate part of the natural
- Ladame, Sylvain,Bardet, Michel,Périé, Jacques,Willson, Michèle
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p. 773 - 783
(2007/10/03)
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- Farnesyl pyrophosphate analogs
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The present invention is directed to farnesyl pyrophosphate analogs which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the com
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- A SYNTHESIS OF 15,16-DIMETHOXYERYTHRIN-6-EN-8-ONE
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A synthesis of 15,16-dimethoxyerythrin-6-en-8-one was accomplished using an intramolecular Wadsworth-Emmons reaction for constructing five-membered lactam, indicating a convenient method to the synthesis of the erythrinan skeleton.
- Zhang, Yong,Takeda, Shigeko,Kitagawa, Takao,Irie, Hiroshi
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p. 2151 - 2154
(2007/10/02)
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- Effect of Phosphono Substituents on Acyl Transfer Reactions
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The rate of release of p-nitrophenoxide from esters of phosphono-substituted carboxylic acids was examined as a function of pH(D), temperature, divalent metal ion (Mg2+ and Ca2+) concentration, and acyl acceptor (-OH and the thiolate of N-acetylcysteine).The hydrolysis of p-nitrophenyl 3-phosphonopropionate involves intramolecular nucleophilic catalysis by the dianionic phosphono substituent (pKa2(*) = 7.5) and is characterized by a first-order rate constant of 94 min-1 at 37 deg C.A comparison of the rate constant of the unimolecular reaction with that of the corresponding bimolecular reaction (corrected for the inductive effect of the acyl substituent and for the phosphonate basicity) yields a rate constant ratio of kuni/kbi = 7(+/-6)*103 M.The magnitude of this rate enhancement is similar to those of analogous intramolecular reactions (e.g., hydrolysis of mono-p-nitrophenyl succinate or of p-nitrophenyl 4-(N,N-dimethylamino)butyrate but, unlike these reactions, the rate acceleration resulting from intramolecular nucleophilic catalysis by the dianionic phosphono group is enthalpic in origin (Δ(*) ca. 8 kcal/mol).The entropy of activation for the intramolecular reaction is less favorable than that for the bimolecular reaction (Δ(*) ca. 9 eu).The alkaline hydrolysis and the thiolysis rates of p-nitrophenyl phosphonoacetate are accelerated over 100-fold by the association of Mg2+ or Ca2+ with the ester.This rate acceleration is attributed to the formation of a six-membered bidentate coordination complex between the divalent cation and the incipient tetrahedral intermediate.The metal-promoted acyl transfer reactions of p-nitrophenyl phosphonoacetate provide a convenient system for the quantitative assessment of the role of metal ions in the catalysis of aqueous reactions.
- Shames, Spencer L.,Byers, Larry D.
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p. 6177 - 6184
(2007/10/02)
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- PHOSPHONOACYL PROLINES AND RELATED COMPOUNDS
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New phosphonoacyl prolines and related compounds have the general formula STR1 wherein R 1 and R 2 each is hydrogen, lower alkyl, lower alkenyl, unsustituted or substituted phenyl-lower alkyl, or a metal ion;R 3 is hydrogen or lower alkyl; R 4 is hydrogen, lower alkyl, phenyl-lower alkyl or a metal ion; andN IS 0 OR 1. These compounds are useful as hypotensive agents.
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