125734-44-3Relevant articles and documents
Use of the Kohonen neural network for rapid screening of ex vivo anti-HIV activity of styrylquinolines
Polanski, Jaroslaw,Zouhiri, Fatima,Jeanson, Laurence,Desma?le, Didier,D'Angelo, Jean,Mouscadet, Jean-Fran?ois,Gieleciak, Rafal,Gasteiger, Johann,Le Bret, Marc
, p. 4647 - 4654 (2002)
Using the Kohonen neural network, the electrostatic potentials on the molecular surfaces of 14 styrylquinoline derivatives were drawn as comparative two-dimensional maps and compared with their known human immunodeficiency virus (HIV)-1 replication blocki
Reversing Chemoselectivity: Simultaneous Positive and Negative Catalysis by Chemically Equivalent Rims of a Cucurbit[7]uril Host
Rad, Nazar,Danylyuk, Oksana,Sashuk, Volodymyr
, p. 11340 - 11343 (2019/07/16)
Enzyme catalysis has always been an inspiration and an unattainable goal for chemists due to features such as high specificity, selectivity, and efficiency. Here, we disclose a feature neither common in enzymes nor ever described for enzyme mimics, but one that could prove crucial for the catalytic performance of the latter, namely the ability to catalyze and inhibit two different reactions at the same time. Remarkably, this can be realized by two identical, spatially resolved catalytic sites. In the future, such a synchronized catalyst action could be used not only for controlling chemoselectivity, as in the present case, but also for regulating other types of chemical reactivity.
ETHER COMPOUNDS AND USES THEREOF
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Paragraph 0183, (2019/03/12)
The present invention provides compounds that modulate protein function, to restore protein homeostasis and/or cell-cell adhesion. The invention provides methods of modulating protein-mediated diseases, such as cytokine-mediated diseases, disorders, conditions, or responses. Compositions of these compounds are also provided. Methods of treatment, amelioration, or prevention of protein-mediated diseases, disorders, and conditions are also provided.
Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
, p. 10145 - 10149 (2016/08/16)
A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
GLUCOSE SENSOR MOLECULE
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Page/Page column 14-15, (2012/07/28)
The present invention provides a glucose sensor having a glucose receptor containing a binding site of formula (I): wherein X, n, m and R1 are defined herein. Also provided is a glucose sensor molecule for use in such a glucose sensor, the glucose sensor molecule containing the binding site of formula (I). The binding site has been found to have particularly good selectivity for glucose.
Novel monocyclam derivatives as HIV entry inhibitors: Design, synthesis, anti-HIV evaluation, and their interaction with the CXCR4 co-receptor
Pettersson, Sofia,Perez-Nueno, Violeta I.,Mena, Maria Pau,Clotet, Bonaventura,Este, Jose A.,Borrell, Jose I.,Teixido, Jordi
scheme or table, p. 1272 - 1281 (2011/02/21)
The CXCR4 receptor has been shown to interact with the human immunodeficiency virus (HIV) envelope glycoprotein gp120, leading to fusion of viral and cell membranes. Therefore, ligands that can attach to this receptor represent an important class of therapeutic agents against HIV, thus inhibiting the first step in the cycle of viral infection: the virus-cell entry/ fusion. Herein we describe the in silico design, synthesis, and biological evaluation of novel monocyclam derivatives as HIV entry inhibitors. In vitro activity testing of these compounds in cell cultures against HIV strains revealed EC50 values in the low micromolar range without cytotoxicity at the concentrations tested. Docking and molecular dynamics simulations were performed to predict the binding interactions between CXCR4 and the novel monocyclam derivatives. A binding mode of these compounds is proposed which is consistent with the main existing site-directed mutagenesis data on the CXCR4 coreceptor. Moreover, molecular modeling comparisons were performed between these novel monocyclams, previously reported non-cyclam compounds from which the monocyclams are derived, and the well-known AMD3100 bicyclam CXCR4 inhibitors. Our results suggest that these three structurally diverse CXCR4 inhibitors bind to overlapping but not identical amino acid residues in the transmembrane regions of the receptor.
Binding of acetylcholine and tetramethylammonium to flexible cyclophane receptors: Improving on binding ability by optimizing host's geometry
Sarri, Paolo,Venturi, Francesca,Cuda, Francesco,Roelens, Stefano
, p. 3654 - 3661 (2007/10/03)
The structure of a cyclophanic tetraester (1), previously employed for investigations on the cation-π interaction, has been optimized to better accommodate acetylcholine (ACh) and tetramethylammonium (TMA) guests. Following indications from molecular modeling calculations, a flexible cyclophane receptor of significantly improved binding properties has been obtained by removing the four carbonyl groups of the parent host. 2,11,20,29-Tetraoxa[3.3.3.3]paracyclophane (2) was prepared by an improved procedure, which was conveniently devised to avoid the formation of contiguous cyclooligomers that caused serious separation issues. Association of 2 with TMA picrate was measured in CDCl3 at T = 296 K by 1H NMR titrations and compared to binding data obtained for a set of reference hosts, including the parent tetraester 1, the corresponding cyclophanic tetraamine, the open-chain counterpart of 2, and its cyclooligomers from pentamer to octamer. Binding enhancements ranging from 15-fold (with respect to the tetraester and the tetraamine) to over 80-fold (with respect to the open-chain tetraether) were achieved by geometry optimization of the host. Binding of 2 to ACh and TMA was investigated for a variety of counterions. A constant binding free energy increment of nearly 8 kJ mol-1 with respect to 1 was observed, independent from the anion and irrespective of the different structure of the cationic guests. Results showed that the electrostatic inhibiting contribution of the counterion to the cation's binding is a characteristic constant of each anion. The value of -ΔG° = 44.9 kJ mol-1 extrapolated for TMA in the absence of a counterion indicates that 28-34 kJ mol-1 of binding free energy are lost in ion pairing.
Two-photon absorption in three-dimensional chromophores based on [2.2]-paracyclophane
Bartholomew, Glenn P.,Rumi, Mariacristina,Pond, Stephanie J. K.,Perry, Joseph W.,Tretiak, Sergei,Bazan, Guillermo C.
, p. 11529 - 11542 (2007/10/03)
A series of α,ω-bis donor substituted oligophenylenevinylene dimers held together by the [2.2]-paracyclophane core were synthesized to probe how the number of repeat units and through-space delocalization influence two-photon absorption cross sections. Specifically, the paracyclophane molecules are tetra(4,7,12,15)-(4′-dihexylaminostyryl)[2.2]paracyclophane (3R D), tetra(4,7,12,15)-(4″-(4′-dihexylaminostyryl)styryl) [2.2]paracyclophane (5RD), and tetra(4,7,12,15)-(4?-(4″- (4′-dihexylaminostyryl)styryl)styryl)[2.2]paracyclophane (7RD). The compounds bis(1,4)-(4′-dihexylaminostyryl)benzene (3R) and bis(1,4)-(4″-(4′-dihexylaminostyryl)styryl)benzene (5R) were also synthesized to reveal the properties of the "monomeric" counterparts. The two-photon absorption cross sections were determined by the two-photon induced fluorescence method using both femtosecond and nanosecond pulsed lasers as excitation sources. While there is a red shift in the linear absorption spectra when going from the "monomer" chromophore to the paracyclophane "dimer" (i.e., 3R → 3RD, 5R → 5RD), there is no shift in the two-photon absorption maxima. A theoretical treatment of these trends and the dependence of transition dipole moments on molecular structure rely on calculations that interfaced time-dependent density functional theory (TDDFT) techniques with the collective electronic oscillator (CEO) program. These theoretical and experimental results indicate that intermolecular interactions can strongly affect Bu states but weakly perturb Ag states, due to the small dipole-dipole coupling between Ag states on the chromophores in the dimer.
Synthesis and antirheumatic activity of the metabolites of esonarimod
Noguchi, Toshiya,Onodera, Akira,Tomisawa, Kazuyuki,Yamashita, Miyuki,Takeshita, Kimiyo,Yokomori, Sadakazu
, p. 2713 - 2721 (2007/10/03)
We have developed esonarimod, (±)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid, as a new antirheumatic drug. Now we describe herein the preparation of the enantiomers of (±)-deacetylesonarimod, the pharmaceutically active metabolites of esonar
Practical Synthesis of Vinyl-Substituted p-Phenylenevinylene Oligomers and Their Triethoxysilyl Derivatives
Sugiono, Erli,Metzroth, Thorsten,Detert, Heiner
, p. 351 - 359 (2007/10/03)
Luminescent semiconducting organic compounds are widely used as active layers in electro-optical devices. Apart from conjugated polymers, monodisperse oligomers also represent attractive materials. The synthesis of stilbenoid oligomers with polymerizable
