- A Family of Amphiphilic Cyclodextrin Liquid Crystals Governed by Dipole–Dipole Interactions
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A novel family of amphiphilic cyclodextrin(CD)-based liquid crystals that bear O-acetylated oligoethylene glycol chains at the secondary face is reported. Unlike most of the previously reported liquid crystals (LC) based on chemically modified CDs, which depend on H-bonding as the primary intermolecular forces, the present CD derivatives self-assemble into highly ordered smectic liquid crystal phases via the weaker dipole–dipole intermolecular interactions. The obtained materials are found to display much improved properties such as improved thermostability, reduced clearing temperatures, and better fluidity. The present work opens up new possibilities to design CD-based LC materials.
- Champagne, Pier-Luc,Ester, David,Ward, Sandra,Williams, Vance E.,Ling, Chang-Chun
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- Synthesis Toward and Stereochemical Assignment of Clathsterol: Exploring Diverse Strategies to Polyoxygenated Sterols
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Herein we describe a synthesis of the trisulfate derivative of clathsterol (1), a marine sterol endowed with impressive structural features and moderate inhibitory activity against HIV-1 reverse transcriptase. By synthesizing two possible isomers of the side chain, the stereochemistry of 1 is assigned. In creating chiral side chains from steroidal lactone, our strategies, including an addition/reduction procedure to give C22R-OH, an epoxide-opening reaction, and a [3.3]-rearrangement to induce the generation of C24S-Et and C24R-Et respectively, are highly flexible and complementary to each other.
- Zhou, Tao,Feng, Feng,Shi, Yong,Tian, Wei-Sheng
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- HYDANTOIN CONTAINING DEOXYURIDINE TRIPHOSPHATASE INHIBITORS
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Provided herein are dUTPase inhibitors, compositions comprising such compounds and methods of using such compounds and compositions.
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Paragraph 0927
(2018/06/12)
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- Triazine-Based Cationic Leaving Group: Synergistic Driving Forces for Rapid Formation of Carbocation Species
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A new triazine-based cationic leaving group has been developed for the acid-catalyzed alkylation of O- and C-nucleophiles. There are two synergistic driving forces, namely, stable C=O bond formation and charge-charge repulsive effects, involved in the rapid generation of the carbocation species in the presence of trifluoromethanesulfonic acid (~200 mol %). Considerable rate acceleration of benzylation, allylation, and p-nitrobenzylation was observed as compared to the reactions with less than 100 mol % of the acid catalyst. The triazine-based leaving group showed superior p-nitrobenzylation yield and stability in comparison to common leaving groups, trichloroacetimidate and bromide. A plausible reaction mechanism (the cationic leaving group pathway) was proposed on the basis of mechanistic and kinetic studies, NMR experiments, and calculations.
- Fujita, Hikaru,Kakuyama, Satoshi,Fukuyoshi, Shuichi,Hayakawa, Naoko,Oda, Akifumi,Kunishima, Munetaka
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supporting information
p. 4568 - 4580
(2018/04/26)
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- THIAZOLIDINONE COMPOUNDS AND USE THEREOF
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A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.
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Paragraph 0990-0991
(2017/09/21)
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- A strategy for the targeting of photosensitizers. Synthesis, characterization, and photobiological property of porphyrins bearing glycodendrimeric moieties
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This paper describes the conception, synthesis, and characterization of new tetrapyrrolic chromophores bearing glycodendrimeric moieties inducing a potential increase of tumor targeting by a cluster effect. Two families of monoglycodendrimeric photosensitizers bearing three glycosyl units were designed, prepared with an acceptable overall efficiency and characterized by NMR, UV-visible, and fluorescence spectroscopies. The polarity and log P were evaluated by HPLC and the stir-flask method, respectively. The in vitro photoefficiency against two human tumor cell lines was assessed. The presence of the glycodendrimeric group does not appear to increase the tumor in vitro targeting.
- Ballut, Severine,Naud-Martin, Delphine,Loock, Bernard,Maillard, Philippe
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experimental part
p. 2010 - 2028
(2011/06/17)
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- Synthesis of analogues of Acyclic nucleoside diphosphates containing a (phosphonomethyl)phosphanyl moiety and studies of their phosphorylation
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Acyclic nucleoside diphosphonate derivatives of purines and pyrimidines were prepared by Mitsunobu reaction of suitably protected heterocyclic bases with alcohols containing the (phosphonomethyl)phosphanyl moiety. Furthermore, nonhydrolyzable acyclic analogues of dUDP were prepared as potential inhibitors of dUTPase. Their phosphorylation to analogues of dUTP, however, gave mixtures of linear and branched phosphates. The courses of the phosphorylation reactions were followed by 31P NMR spectroscopy, and we discovered that both phosphonate and phosphinate moieties react with 1,1'-carbonyldiimidazole and tri-n-butylammonium phosphate. The pKa values of the (phosphonomethyl)phosphanyl system were also determined by 31P NMR spectroscopy ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009).
- Dolakova, Petra,Dracinsky, Martin,Fanfrlik, Jindrich,Holy, Antonin
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experimental part
p. 1082 - 1092
(2009/07/19)
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- Heterocyclic benzenesulphonamide compounds as bradykinine antagonists
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The invention concerns compounds selected among the group consisting of (i) compounds of formula (I) wherein: Het1 represents a nitrogenous heterocycle with 5 apices, in particular imidazole, pyrazole, or triazole; Het2 represents a nitrogenous heterocycle with 4, 5 or 6 apices, selected among the heterocycles: (II) wherein R1and R2are defined as mentioned in the description; and (ii) their additive salts. The invention also concerns the method for preparing said compounds and their use in therapy, in particular for treating pathologies involving bradykinine.
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- Kinetics and mechanism of oxidation of aliphatic acetals with N-chlorobenzamide
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The oxidation kinetics of thirteen aliphatic acetals of normal aliphatic aldehydes and substituted aliphatic aldehydes with aliphatic and substituted aliphatic as well as with aromatic alcohols by N-chlorobenzamide (NCB) in aqueous acetic acid medium follows first order and zero order dependence in [NCB] and [acetal] respectively and yields the corresponding esters as the main product of oxidation. (H2OCl)+ has been postulated as the oxidizing species.
- Basheer Ahamed
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p. 222 - 224
(2007/10/03)
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