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At least 343 records · Page 19Linked to original sources
PubMed2006

Photooxidation of acyclovir with thermally generated triplet excited ketones. A comparison with type I and II photosensitizers.

The antiviral drug acyclovir (Ac, 1) was treated with triplet excited ketones, which have been generated in thermal decomposition of 3-(hydroxymethyl)-3,4,4-trimethyl-1,2-dioxetane (HTMD), in the dark. Three major oxidation products were detected by means of spectroscopic measurements. The products were (2-hydroxyethoxy) methyl spiroiminodihydantoin (2), (2-hydroxyethoxy) methyl (amino)-2-imino-1,2-dihydroimidazole-5-one (3), and 2,2-diamino-4-[(2-hydroxyethoxy) methyl) amino)-5-[2H]-oxazolone (4). Equal amounts of type I and type II photooxidation products were found, as could be established by comparison with predominant type I (riboflavin) and type II (rose bengal) photosensitizers. The concentration and time profiles for the HTMD-induced oxidation of Ac were also determined. The participation of singlet oxygen in HTMD-induced oxidation was confirmed by the substantial D(2)O effect in the formation of spiroiminodihydantoin (2).

Acyclovir↗
PubMed2006

Quantitative GC-ECD analysis of halogenated metabolites: determination of surface and within-thallus elatol of Laurencia obtusa.

Information on natural concentrations or variability of secondary metabolites in marine organisms may be important both to ecological/evolutionary and applied approaches. A gas chromatographic procedure with an electron capture detector (GC-ECD) was developed to quantify the sesquiterpenoid elatol at the surface and within-thalli of 70 specimens of the red seaweed Laurencia obtusa. The concentration of elatol was highest within-thalli [9.89 mg g(-1) of L. obtusa, dry weight (d.w.)], compared to lower values found at the surface [0.006 mg g(-1) of L.obtusa (d.w.), or 0.5-10.0 ng cm(-2)]. This method provides a rapid and inexpensive quantification of small quantities of elatol, and probably may also be used to quantify other halogenated compounds usually found in red seaweeds.

Chromatography, Gas↗
PubMed2006

Synthesis of bisbenzannulated spiroketals-model studies for a modular approach to rubromycins.

[reaction: see text] A highly flexible synthesis of bisbenzannulated spiroketals is described with additions of lithiated methoxyallene to aryl aldehydes and Heck reactions as key steps. Subsequent hydrogenations and ketalizations afforded the desired spiroketals in good yields and with predominating trans-configuration. With model compound 30, already bearing the fully substituted naphthyl core of rubromycins, the ketalization proceeded efficiently providing the expected product 31 and the isopropoxy compound 32. Both products are advanced model compounds of heliquinomycin.

Benzoquinones↗
PubMed2000

A novel approach in drug discovery: synthesis of estrone--talaromycin natural product hybrids.

Hetero-Diels-Alder reaction of the steroidal exocyclic enol ethers 14 and 15, obtained from the secoestrones 8 and 9 by reduction, iodoetherification, and elimination, with ethyl O-benzoyldiformylacetate (16) leads to the spiroacetals 17 and 18 as a mixture of four diastereomers. Reduction of the major diastereomers 17a and 18a with DIBAH and subsequent hydrogenation yields the novel natural product hybrids 21, 23, 24, and 25, which possess the structural features of the steroid estrone (7) and the mycotoxin talaromycin 6.

Acetals↗
PubMedDate not supplied

Annulation of primary amines to piperazines and diazaspirocycles utilizing alpha-methyl benzyl resin.

The microwave-assisted solid-phase synthesis of piperazines, 3,9-diazaspiro[5.5]undecanes and 2,9-diazaspiro[5.5]undecanes is reported. The synthesis relies on the direct annulation of primary amines with resin-bound bismesylates. Critical to the success of this chemistry was the development of alpha-methyl benzyl carbamate resin linker. This resin permits the cleavage of the heterocycles under mildly acidic conditions, free of contaminating linker-derived N-alkylated byproducts.

Amines↗
PubMed1970

Detection of griseofulvin and dechlorogriseofulvin by thin-layer chromatography and gas-liquid chromatography.

A rapid and accurate method is described for the determination of griseofulvin and dechlorogriseofulvin extracted from Penicillium urticae with chloroform. Thinlayer chromatography was used to tentatively identify griseofulvin or dechlorogriseofulvin, or both. Two gas-liquid chromatographic systems provided additional qualitative information and simultaneous quantitation of the individual compounds.

Chloroform↗
PubMed2005

Photopolymerization of developmental monomers for dental cationically initiated matrix resins.

OBJECTIVES: The objectives were to investigate the structure and selected physical properties of products resulting from the photopolymerization of a binary mixture containing an aliphatic dioxirane, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate (ECHM-ECHC) and a potential expanding monomer, 3,9-bis(oxiranylcyclohexylmethyl)-1,5,7,11-tetraoxaspiro[5.5]undecane (BOCHM-TOSU). METHODS: Reaction mixtures were irradiated with a dental curing lamp at room temperature. Some reactions were quenched prior to gel point. Oligomeric products were separated from unreacted monomers by column chromatography, and analyzed by NMR. Physical properties of polymeric solids were measured using accepted standard methods. Protonation energies for monomers were calculated using semi-empirical quantum mechanical methods. RESULTS: Types of oligomers found included poly(ether)s and poly(carbonate)s. Quantum mechanical calculations indicated preferential attack at the more nucleophilic oxaspirocyclic ring sites. For cured solid polymer samples, the elastic modulus was 2.39 +/- 0.24 GPa and the fracture toughness was 0.73 +/- 0.10 MPa m(1/2). These values were similar to those measured for a cured conventional BISGMA/TEGDMA matrix resin. SIGNIFICANCE: The room-temperature photopolymerization of an aliphatic dioxirane and a potential expanding monomer demonstrates the possibility of making cross-linked copolymer resins with improved polymerization shrinkage characteristics for use in dental composites.

Alkanes↗
PubMed2006

Plasmodium vivax: in vitro susceptibility of blood stages to synthetic trioxolane compounds and the diamidine DB75.

Plasmodium vivax is an important human pathogen causing malaria in more temperate climates of the world. Similar to Plasmodium falciparum, the causative agent for malaria tropica, drug resistance is beginning to emerge for this parasite species and this hampers adequate treatment of infection. We have used a short-term ex vivo drug assay to monitor activity of OZ277 (RBx-11160), a fully synthetic anti-malarial peroxide, and the diamidine DB75 against P. vivax. For both compounds as well as the anti-malarial reference compounds artesunate, artemether, and chloroquine, the in vitro IC(50) values were determined in one-cycle hypoxanthine incorporation assays. Results from such assays were found to be very similar compared to IC(50) values obtained from one-cycle P. falciparum hypoxanthine assays. We demonstrate the anti-parasite activity of OZ277 and the reference compounds to be faster than that of DB75. These data warrant clinical testing of OZ277 against P. vivax malaria and support recent data on clinical activity against P. vivax for DB75.

Animals↗
PubMed1997

[3H]Alnespirone: a novel specific radioligand of 5-HT1A receptors in the rat brain.

Determination of the optimal assay conditions for the specific binding of a tritiated derivative of the novel potential anxiolytic drug alnespirone (S-20499, (+)-4-[N-(5-methoxy-chroman-3-yl)-N-propylamino]butyl-8-azaspiro-( 4,5)-decane-7,9-dione) allowed the demonstration that this radioligand bound with a high affinity (Kd = 0.36 nM) to a homogeneous class of sites in rat hippocampal membranes. The pharmacological properties of [3H]alnespirone specific binding sites matched exactly (r = 0.95) those of 5-HT1A receptors identified with [3H]8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) as radioligand. Furthermore, membrane binding experiments and autoradiographic labeling of tissue sections showed that the regional distribution of [3H]alnespirone specific binding sites in the rat brain and spinal cord superimposed over that of 5-HT1A receptors specifically labeled by [3H]8-OH-DPAT. However, the differential sensitivity of [3H]alnespirone and [3H]8-OH-DPAT specific binding to various physicochemical effectors (temperature, pH, Mn2+, N-ethyl-maleimide) supports the idea that these two agonist radioligands did not recognize 5-HT1A receptors exactly in the same way. These differences probably account for the reported inability of alnespirone, in contrast to 8-OH-DPAT, to induce some 5-HT1A receptor-mediated behavioural effects in rats.

8-Hydroxy-2-(di-n-propylamino)tetralin↗
PubMed2005

First synthesis and evaluation of the inhibitory effects of aza analogues of TSAO on HIV-1 replication.

Aza TSAO-T derivatives bearing a dihydroisothiazole dioxide ring instead of an oxathiole dioxide ring at the C-3' position on the sugar moiety were prepared. We have synthesized four families of compounds depending on substitution at both N-3 and N-2' '. Biological evaluation showed that these compounds are HIV-1(III(B))-specific and potent reverse transcriptase inhibitors with EC(50) values between 0.13 and 3.5 microM in cell culture.

Aza Compounds↗
PubMed2006

Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

Berkeley Pit Lake is an abandoned open-pit copper mine filled with 30 billion gallons of acidic, metal-contaminated water. This harsh environment is proving to be a source of unusual microorganisms that produce novel bioactive metabolites. Bioassay-guided fractionation using signal transduction enzyme assays led to the isolation of the novel spiroketal, berkelic acid 1, and of the known gamma-pyrone, spiciferone A 4. Berkelic acid has shown selective, nanomolar activity against OVCAR-3, an ovarian cancer cell line in the National Cancer Institute cell line screen. The isolation and characterization of these compounds are reported here.

Antineoplastic Agents↗
PubMed2001

A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) coupling approach to the phomactins.

[reaction: see text] Through a unified synthetic strategy, appropriately functionalized bicyclic starting materials can be elaborated via Ni(II)/Cr(II) macrocylization to [9.3.1] bicycles. Elaboration of these core structures allows access to phomactin C/D analogues and establishes the first synthetic approach to phomactin A affording an intact octahydrochromene/macrocyclic ring system.

Animals↗