- Anti-HIV-Active Nucleoside Triphosphate Prodrugs
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We disclose a study on nucleoside triphosphate (NTP) analogues in which the γ-phosphate is covalently modified by two different biodegradable masking units and d4T as nucleoside analogue that enable the delivery of d4TTP with high selectivity in phosphate buffer (pH 7.3) and by enzyme-triggered reactions in human CD4+ T-lymphocyte CEM cell extracts. This allows the bypass of all steps normally needed in the intracellular phosphorylation. These TriPPPro-nucleotides comprising an acyloxybenzyl (AB; ester) or an alkoxycarbonyloxybenzyl (ACB; carbonate) in combination with an ACB moiety are described as NTP delivery systems. The introduction of these two different groups led to the selective formation of γ-(ACB)-d4TTPs by chemical hydrolysis and in particular by cell extract enzymes. γ-(AB)-d4TTPs are faster cleaved than γ-(ACB)-d4TTPs. In antiviral assays, the compounds are highly active against HIV-1 and HIV-2 in wild-type CEM/O cells and more importantly in thymidine kinase-deficient CD4+ T-cells (CEM/TK-).
- Jia, Xiao,Schols, Dominique,Meier, Chris
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- Synthesis, physicochemical properties and biological activities of novel alkylphosphocholines with foscarnet moiety
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A series of alkylphosphocholines with foscarnet moiety was synthesized. The structure of these zwitterionic amphiphiles was modified in both polar and non-polar parts of surfactant molecule. Investigations of physicochemical properties are represented by the determination of critical micelle concentration, the surface tension value at the cmc and the surface area per surfactant head group utilising surface tension measurements. Hydrodynamic diameter of surfactant micelles was determined using the dynamic light scattering technique. Alkylphosphocholines exhibit significant cytotoxic, anticandidal (Candida albicans) and antiamoebal (Acanthamoeba spp. T4 genotype) activity. The relationship between the structure, physicochemical properties and biological activity of the tested compounds revealed that lipophilicity has a significant influence on biological activity of the investigated surfactants. More lipophilic alkylphosphocholines with octadecyl chains show cytotoxic activity against cancer cells which is higher than that of the compounds with shorter alkyl chains. The opposite situation was observed in case of anticandidal and antiamoebal activity of these surfactants. The most active compounds were found to have pentadecyl chains. The foscarnet analogue of miltefosine C15-PFA-C showed the highest anticandidal activity. The minimum value of anticandidal activity of this compound is 1,4 μM thus representing the highest anticandidal activity found within the group of alkylphosphocholines.
- Mrva, Martin,Bukovsky, Marián,Devínsky, Ferdinand,Garajová, Mária,Juhásová, Anna,Luká?, Milo?,Moj?i?, Ján,Moj?i?ová, Gabriela,Pisár?ik, Martin,Timko, Luká?
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- Synthesis method of photosensitive material stabilizing agent of 4-hexadecyloxy carbonyloxy-3,5-dichlorobenzene ethyl formate
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The invention relates to a novel synthesis method of a photosensitive material stabilizing agent of 4-hexadecyloxy carbonyloxy-3,5-dichlorobenzene ethyl formate. 4-hydroxyl-3,5-dichlorobenzene ethyl formate is used as raw materials to take a reaction with hexadecyloxy carbonyl acyl chloride under the effect of acid-binding agents to obtain the 4-hexadecyloxy carbonyloxy-3,5-dichlorobenzene ethyl formate. The invention relates to a synthesis method of intermediates of 4-hydroxy-3,5-dichlorobenzene ethyl formate and the hexadecyloxy carbonyl acyl chloride, and the optimum reaction condition of the synthesis of the 4-hexadecyloxy carbonyloxy-3,5-dichlorobenzene ethyl formate, and provides a novel economical and practical method realizing simple operation.
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Paragraph 0021; 0022; 0024
(2017/07/21)
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- Fluorescent gelators for detection of explosives
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Carbazole-, quinoline-, benzothiazole-, and stilbene-containing fluorescent gelators are synthesized by connecting gelationdriving segments, and their gelation abilities are studied with 13 solvents. Fibrous thin-layer films are prepared on quartz plates
- Hanabusa, Kenji,Takata, Shingo,Fujisaki, Masafumi,Nomura, Yasushi,Suzuki, Masahiro
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p. 1391 - 1401
(2017/08/02)
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- Pyrene-derived novel one- and two-component organogelators
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A new class of alkyl-chainappended pyrene derivatives 4 - 14 were synthesized and evaluated for their gelation abilities. Depending on the nature of the linking group, these compounds gelated a number of organic solvents, either in the presence or in the absence of the acceptor molecule 2,4,7-trinitrofluorenone (TNF). Compounds with ester, ether, or alkyl linkages gelated a number of hydroxylic and hydrocarbon solvents by means of a charge-transfer interaction with TNF, while compounds with amide, urethane and urea linkers formed gels on their own in a variety of solvents by means of π-π stacking and hydrogen-bonding interactions. The X-ray crystal structure of urethane (S)-12 showed hydrogen-bonding and stacking features, as suggested by the model. The gels obtained were investigated by spectroscopic and electron microscopic techniques which provided structural insights.
- Babu,Sangeetha,Vijaykumar,Maitra, Uday,Rissanen, Kari,Raju
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p. 1922 - 1932
(2007/10/03)
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- A safe and efficient procedure to prepare alkyl and alkoxyalkyl chlorides and dichlorides by catalytic decomposition of the corresponding alkyl and alkoxyalkyl chloroformates and bischloroformates with hexabutylguanidinium chloride
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Small amounts of hexabutylguanidinium chloride (0.01 mol%) decomposes pure chloroformates or bischloroformates with different lengths of carbon chains by a semicontinuous process to diminish run-away risk, leading to chloride compounds with high yield and purity.
- Violleau,Thiebaud,Borredon,Le Gars
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p. 367 - 373
(2007/10/03)
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- New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin
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Irradiation with visible light of S-alkoxycarbonyl xanthates derived from various alcohols gives rise to alkoxycarbonyl radicals with bifurcate reactivity: loss of carbon dioxide leads to deoxygenated derivatives (i.e. alkyl xanthates) whereas intramolecular addition to a suitably located double bond produces lactones; these new reactions were applied to the total synthesis of (±)-cinnamolide and (±)-methylenolactocin.
- Forbes, Judith E.,Saicic, Radomir N.,Zard, Samir Z.
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p. 3791 - 3802
(2007/10/03)
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- Heat-sensitive recording materials and phenol compounds
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Heat-sensitive recording materials contain an electron-donating chromogenic compound and an electron-attracting compound. The recording materials also contain at least one compound represented by the following formula: STR1 wherein R1 and R3 mean a hydrogen atom or an alkyl, aralkyl or aryl group, R2 and R4 denote an alkyl, alkenyl, aralkyl or aryl group, X1, X2, Y1 and Y2 stand for an oxygen or a sulfur atom, and --Z1 -- and --Z2 -- are a specific aromatic group. Also provided are phenol compounds represented by the following formula: STR2 wherein R1, R2, X1 and Y1 have the same meanings as defined above; R5 and R6 are a hydrogen or halogen atom or an alkyl, alkoxy, aralkyl, aryl or hydroxyl group; p and q stand for an integer of 1-4; R5 and R6 may be either the same or different when p and q represent an integer of 2 or greater; and --Z3 -- means a specific divalent group.
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