- New Photochemically Labile Protecting Group for Phosphates
-
New photochemically labile phosphate protecting group was developed.These phosphate esters have high molar extinction coefficient (ε340=34500 dm3 mol-1cm-1) and rapidly release parent phosphates upon irradiation (>300 nm) with high quantum efficiency for disappearance (φdis=0.22 at 340 nm).
- Furuta, Toshiaki,Torigai, Hiromi,Osawa, Tomoko,Iwamura, Michiko
-
-
Read Online
- Novel photolabile protecting group for phosphate compounds
-
A novel photolabile protecting group, thiochromone S,S-dioxide, containing the diazomethyl group for protection of phosphate derivatives is described. Deprotection of the successfully protected phosphate derivatives proceeded smoothly under photoirradiation using an ultrahigh-pressure mercury lamp to recover the corresponding phosphates quantitatively, and the photoproduct derived from the thiochromone derivative showed high fluorescence intensity. Georg Thieme Verlag Stuttgart · New York.
- Zhang, Youlai,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Morimoto, Tsumoru,Kakiuchi, Kiyomi
-
scheme or table
p. 367 - 370
(2012/03/11)
-
- MANNOSE PHOSPHATE DERIVATIVES AS ANTAGONISTS OF BACTERIAL ADHESION
-
Compounds of the formula (I) (I) wherein n is 0, 1 or 2, R1 is aryl, heteroaryl or heterocyclyl, and R2 and R3 are, independent of each other, hydrogen or a substituent as described in the specification, and one of RA, RB, RC and RD is P02(OH)2 and the other ones are hydrogen; are orally available medicaments useful for the prevention and treatment of bacterial infections, in particular of urinary infections caused by E. coli.
- -
-
Page/Page column 45
(2013/02/28)
-
- Efficient catalyst turnover in the phosphitylation of alcohols with phosphoramidites
-
We report a method for catalytic phosphitylation utilizing phosphoramidites. Traditionally, this reaction is inefficient unless an excess of catalyst is present due to catalyst deactivation by an amine by-product. Isocyanate additives have been evaluated
- Brady, Patrick B.,Morris, Elizabeth M.,Fenton, Owen S.,Sculimbrene, Bianca R.
-
scheme or table
p. 975 - 978
(2009/05/27)
-
- IMMUNOMODULATORY COMPOUNDS AND TREATMENT OF DISEASES RELATED TO AN OVERPRODUCTION OF INFLAMMATORY CYTOKINES
-
Method of using immunomodulatory compounds for treating diseases related to an overproduction of inflammatory cytokines, including diseases selected from asthma, atopic dermatitis, allergic rhinitis, prostatitis, inflammatory bowel disease, diabetes, and rhumatoid arthritis, the compounds being of general formula (I): wherein: m and n, independently from each other, are an integer ranging from 1 to 4,X and Y represent —COOH, —O—P(O)(OH)2, —O—SO2(OH), —NH2, —OH, —CONH(CH2)n1—NH2, —CO—NH—CH(COOH)—(CH2)n1—COOH, —CO—NH—CH(COOH)—(CH2)n1—NH2, —O—CO—(CH2)n1—NH2, —O—CO—(CH2)n1—CHOH—CH2OH, —O—CO—(CH2)n1—OH, O—CO—(CH2)n1—COOH, —O—CO—(CH2)n1—CHO, —O—CO—(CH2)n1—NH—CO—(CH2)n2—COOH,R1 and R2 each designate an acyl group derived from a saturated or unsaturated, straight- or branched-chain carboxylic acid having from 2 to 18 carbon atoms, which is unsubstituted or bears one to three substituents selected among hydroxyl, dihydroxyphosphoryloxy, alkyl of 2 to 10 carbon atoms, alkoxy of 2 to 10 carbon atoms, acyloxy of 2 to 18 carbon atoms in the acyl moiety, amino, acylamino.
- -
-
-
- Novel acyl-dipeptide-like compounds bearing an accessory functional side chain spacer, a method for preparing the same and pharmaceutical compositions containing such products
-
The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.
- -
-
-
- Tubulin binding ligands and corresponding prodrug constructs
-
A diverse set of tubulin binding agents have been discovered which are structurally characterized, in a general sense, by a semi-rigid molecular framework capable of maintaining aryl-aryl, pseudo pi stacking distances appropriate for molecular recognition of tubulin. In phenolic or amino form, these ligands may be further functionalized to prepare phosphate esters, phosphate salts, phosphoramidates, and other prodrugs capable of demonstrating selective targeting and destruction of tumor cell vasculature.
- -
-
-
- Acyl pseudodipeptides which carry a functionalised auxialiary arm
-
The present invention is directed in particular to dipeptide-like compounds derived from functionally substituted amino acids, having fatty acid chains bound thereto through amidification of the amine functional groups of said dipeptide-like compounds, one end portion of which bears an accessory functional side chain spacer, with the other end portion being an acid group either in neutral or charged state. Compounds of the present invention have immunomodulating properties like adjuvants, In addition, compounds of the invention can be grafted on a given antigen in order to modulate or tune the immune response or can be equally grafted on a pharmaceutical carrier to enhance the therapeutic effect or targetting thereof. Accordingly, compounds of the invention find use in human and veterinary medicine both as immunogens and diagnostic tools.
- -
-
-
- Substrate analogs that substitute for lipid I as a substrate for MurG
-
General methods for monitoring the activity of MurG, a GlcNAc transferase involved in bacterial cell wall biosynthesis, is disclosed. More particularly, the synthesis of simplified substrate analogs of Lipid I (the natural substrate for MurG), which function as acceptors for UDP-GlcNAc in an enzymatic reaction catalyzed by MurG, is described. Assays using the substrate analogs of the invention are further disclosed, which are useful for identifying a variety of other substrates, including inhibitors of MurG activity, for facilitating mechanistic and/or structural studies of the enzyme and for other uses. High throughput assays are also described.
- -
-
-
- Tetrahydrofuran antifungal phosphate
-
A compound of the formula I STR1 wherein G is H or PO3 H2 or a pharmaceutical acceptable salt thereof, pharmaceutical compositions containing such compounds and method of using such compounds or pharmaceutical compositions containing them to treat or prevent fungal infection are disclosed.
- -
-
-
- Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin
-
An improved procedure to accomplish the O-phosphorylation of 4-hydroxy- N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-O-benzylpyrophosphate. The O- benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following catalytic O- debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.
- Nichols, David E.,Frescas, Stewart
-
p. 935 - 938
(2007/10/03)
-
- Prodrugs of paclitaxel derivatives
-
The present invention concerns novel paclitaxel derivatives, their use as antitumor agents, and pharmaceutical formulations.
- -
-
-
- Lipopeptide derivatives
-
The present invention is directed to water-soluble derivatives of antibiotic lipopeptides having the formula. STR1 wherein R is H or OH and R' is a phosphono, sulfo or acyl radical possessing a charged group at neutral pH. The derivatives are esters but having a charged group, have good solubility properties in aqueous medium, rendering them more useful as therapeutic agents.
- -
-
-
- A NEW, CONVENIENT AND EFFICIENT GENERAL PROCEDURE FOR THE CONVERSION OF ALCOHOLS INTO THEIR DIBENZYL PHOSPHOROTRIESTERS USING N,N-DIETHYL DIBENZYL PHOSPHORAMIDITE
-
A general procedure is described for the near-quantitative preparation of alkyl dibenzyl phosphates by treating primary, secondary or tertiary alcohols with N,N-diethyl dibenzyl phosphoramidite/1H,5-methyltetrazole followed by mild oxidation of the resultant alkyl dibenzyl phosphites with 3-chloroperoxybenzoic acid.
- Perich, J. W.,Johns, R. B.
-
p. 101 - 102
(2007/10/02)
-
- HYDROLYSE BASIQUE COMPAREE D'ESTERS ALLOPHANIQUES ET PHOSPHORIQUES EN MILIEU MIXTE ACETONITRILE/EAU FAIBLEMENT AQUEUX; MISE EN EVIDENCE D'UNE ENTITE CATALIQUE, INTERMEDIARE DE LA REACTION ENTRE BASE ET SOLVANT
-
Kinetic study of base catalysed hydrolysis in acetonitrile-water mixtures of allophanic esters (models of carboxybiotine) and phosphoric esters shows in the range of low water content (less than 1 molar) an enhancement in rate (103) with a maximum at 0.1-0.3 molar in water.This rate enhancement is ascribed to ground state desolvation and the maximum is interpreted by a change in the rate determining step: leaving group departure in the tetrahedral intermediate is indeed the slow step for the reactions in acetonitrile/water mixture less than 0.1 molar in water.For charged phosphoric esters the rate enhancement from an aqueous medium (pH=10) to organic is larger since as high as 106.On the other hand, in such a medium, an additional catalytic effect is observed; it is shown that it is due to the formation of a reactive species which results from reaction of the base on acetamide when accumulated in the medium from base catalysed hydrolysis of the solvent.
- Monnier, Par E.,Botella, J. M.,Murillo, A.,Klaebe, A.,Perie, J.
-
p. 1315 - 1332
(2007/10/02)
-
- Phosphorylation with Pyrophosphoric Acid
-
Dihydrogenphosphates of primary and secondary aliphatic alcohols as well as phenol were prepared by a very simple procedure with pyrophosphoric acid. t-Butyl and benzyl dihydrogenphosphates could be obtained by a slight modification of the reaction conditions.For the purpose of phosphorylation pyrophosphoric acid was more reactive than orthophosphoric acid.
- Yamaguchi, Hachiro,Ogura, Fumio,Otsubo, Tetsuo,Ikeura, Yasuhiro
-
p. 1891 - 1892
(2007/10/02)
-