- Structure-activity relationship (SAR) studies on the mutagenic properties of 2,7-diaminofluorene and 2,7-diaminocarbazole derivatives
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We discovered that 2,7-diaminofluorene or 2,7-diaminocarbazole moiety can be employed as a core structure of highly effective NS5A inhibitors that are connected through amide bonds to proline-valine-carbamate motifs. Amide bonds can be easily cleaved via various metabolic pathways upon administration into the body, and metabolites containing 2,7-diaminofluorene and 2,7-diaminocarbazole core structures have been known to be strong mutagens. To avoid the mutagenesis issue of these core structures, we examined various functional groups at the C9 or N9 position of 2,7-diaminofluorene or 2,7-diaminocarbazole, respectively, through the Ames test in TA98 and TA100 mutants of Salmonella typhimurium LT-2. We discovered that, through proper alkyl substitution at the C9 or N9 position, 2,7-diaminofluorene and 2,7-diaminocarbazole moieties can be successfully employed in drug discovery without necessarily causing mutagenicity problems.
- Kim, Byeong Wook,Lee, Hwa,Keum, Gyochang,Kim, B. Moon
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- Expanded hexapyrrolohexaazacoronenes. Near-infrared absorbing chromophores with interrupted peripheral conjugation
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A family of azacoronenes containing up to two saturated bridges at the periphery was synthesized from substituted hexapyrrolylbenzenes using a two-step condensation-aromatization procedure. The introduction of peripheral bridges provides access to nonplanar, sterically crowded systems that display complex reactivity patterns, involving stereospecific aromatization of bridges and nucleophile additions. Despite the interrupted conjugation on the periphery, the new azacoronenes have easily accessible higher oxidation levels, and a quadruply charged species was chemically generated by reaction with SbCl5. These oxidized species show extensive π-electron conjugation and are efficient UV-vis-NIR absorbers, active up to ca. 2400 nm. Interruption of peripheral conjugation is shown to induce a tendency toward biradicaloid electron configurations in doubly oxidized species.
- Goka, Elzbieta,Chmielewski, Piotr J.,Lis, Tadeusz,Stpie, Marcin
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p. 16399 - 16410
(2015/02/05)
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- Amphiphilic dendritic dipeptides and their self-assembly into helical pores
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An amphiphilic dendritic dipeptide, comprises a dipeptide(s) comprising one or more of a naturally occurring or synthetic amino acids and a dendron. These are suitable for use in various formulations, films, coatings, membranes and sensors, among other ap
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Page/Page column 45
(2008/06/13)
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- Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents
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Structure-activity relationship studies of a new series of tripentones (thieno[2,3-b]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2,3-b]pyrrolizin-8-one 20 (leukemia L1210, IC50 = 15 nM) was shown to be a potent inhibitor of tubulin polymerization.
- Lisowski, Vincent,Enguehard, Cecile,Lancelot, Jean-Charles,Caignard, Daniel-Henri,Lambel, Stephanie,Leonce, Stephane,Pierre, Alain,Atassi, Ghanem,Renard, Pierre,Rault, Sylvain
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p. 2205 - 2208
(2007/10/03)
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- Synthesis and characterization of end-functionalized oligo- (vinylthiophenes) with liquid crystal properties
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A general scheme for the synthesis of end-functionalized conjugated (E)-vinylthiophene oligomers with liquid crystal and potential second-order non-linear optical properties is described. These push-pull thiophene-containing aromatic molecules show mesogenic properties over different temperature ranges depending on the chain length and the functional end-groups.
- Maertens, Christophe,Zhang, Jian-Xin,Dubois, Philippe,Jerome, Robert
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p. 713 - 718
(2007/10/03)
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- Molecular Recognition Directed Self-Assembly of Tubular Liquid Crystalline and Crystalline Supramolecular Architectures from Taper Shaped (15-Crown-5)methyl 3,4,5-Tris(p-alkyloxybenzyloxy)benzoates and (15-Crown-5-)methyl 3,4,5-Tris(p-dodecyloxy)benzoate
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The syntheses and characterization of a series of (15-crown-5-)methyl 3,4,5-tris(p-alkyloxybenzyloxy)benzoates with alkyl tails of four 25, six 26, and twelve 27 carbon atoms and of (15-crown-5-)methyl 3,4,5-tris(p-dodecyloxybenzoate) 28 are described.Complexation of the crown ether endo-receptor with NaCF3SO3 destabilizes the crystalline phase of 25, 26, 27 and 28 and induces for the case of 27 and 28 the self-assembly of a supramolecular cylindral channel-like architecture which displays a thermotropic hexagonal columnar (Φh) mesophase.Most remarkably, in the crystalline phase of the complexes of 27 with NaCF3SO3 the cylindrical structure of the Φh mesophase is maintained.Characterization of these supramolecular architectures was performed by a combination of differential scanning calorimetry (DSC), thermal optical polarized microscopy, X-ray scattering and molecular modelling.A model is proposed in which a stratum of the column is formed by six molecules of 27 and 28 with the crown ether receptors residing in the column centre and the alkyl tails radiating toward the column periphery. endo-Recognition generated via the (15-crown-5)methyl receptor upon complexation, and exo-recognition provided by the tapered 3,4,5-tris(p-dodecyloxybenzyloxy)benzoate and 3,4,5-tris(p-dodecyloxy)benzoate fragments of 27 and 28 provide the driving force for the self-assembly of this cylindrical supramolecule.
- Johansson, Gary,Percec, Virgil,Ungar, Goran,Abramic, Darija
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p. 447 - 460
(2007/10/02)
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- Liquid crystalline cyclohexylphenyl derivatives
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Cyclohexylphenyl derivatives of the formula STR1 wherein X is --CH2 --CH2 --, --CH2 --O--, --CH2 --S--, --O--CH2 -- or --S--CH2 --; R1 is alkyl of up to 8 carbon atoms; R2/
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