- Enhancing Insulated Conjugated Polymer Fluorescence Quenching by Incorporating Dithia[3.3]paracyclophanes
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Insulated π-conjugated polymers exhibit enhanced chemical stability, photostability, fluorescence quantum yield, electroluminescence, solubility, and intrachain charge transport. However, insulated polymer fluorescence quenching by acceptor molecules is significantly hampered as the π-face is insulated. Photoinduced charge transfer is one of the key steps in amplified fluorescence quenching sensors and organic solar cells for charge generation. Inspired by the myelin sheath gaps in nerve cell axons, herein, we synthesized a series of insulated random copolymers of adamantanocyclophane with an increasing percentage of dithia[3.3]paracyclophane (PCP) from 5 to 30% to enhance the insulated polymer fluorescence quenching with acceptor molecules. As the percentage of the dithia[3.3]paracyclophane monomer increases, the copolymers showed an increase in absorption in the red region of the spectrum and also the copolymers' photoluminescence quantum yield reduced. The Stern-Volmer quenching constant of the 30% copolymer is ca. 4.5 times higher than that of the adamantanocyclophane homopolymer. A comparison with the control polymers indicated that the through-space-coupled interactions in PCP could be a plausible reason for the enhanced fluorescence quenching in copolymers in addition to the reduced steric hindrance by PCP. The developed copolymers combine the advantages of polymer insulation without significantly sacrificing the photoinduced charge transfer, which will help further their applicability as amplified fluorescence quenching sensors and in organic solar cells.
- Lillis, Ryan,Thomas, Maximillian R.,Mohanan, Manikandan,Gavvalapalli, Nagarjuna
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p. 3112 - 3119
(2021/05/05)
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- Synthesis and cytotoxicity of novel simplified eleutherobin analogues as potential antitumour agents
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Mixed simplified structures containing the paclitaxel and eleutherobin pharmacophore moieties were analyzed using molecular docking techniques and synthesized based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds. The crucial role of substituents' stereochemistry in biological activity is discussed. At micromolar concentrations the selected analogues interfered with tubulin dynamics in vitro and in a living organism. Furthermore, new compounds were cytotoxic against human tumour cell lines. The simplified eleutherobin analogues may be considered as prototypes of a new class of antitumour agents.
- Sosonyuk, Sergey E.,Peshich, Anita,Tutushkina, Anastasia V.,Khlevin, Dmitry A.,Lozinskaya, Natalia A.,Gracheva, Yulia A.,Glazunova, Valeria A.,Osolodkin, Dmitry I.,Semenova, Marina N.,Semenov, Victor V.,Palyulin, Vladimir A.,Proskurnina, Marina V.,Shtil, Alexander A.,Zefirov, Nikolay S.
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p. 2792 - 2797
(2019/03/12)
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- Amantadine nitrate compounds with neural protective effect, and preparation and medical use thereof
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The present invention relates to amantadine nitrate compounds having neural protective effect, and preparation method and medical use thereof. The compounds have the structure of the general formula (I). The compounds have multifunctional mechanisms, including inhibiting NMDA receptors, releasing NO, inhibiting calcium influxes, and having protective effects on cells particularly neurocytes. The compounds can be used in the preparation of medicaments having a cellular protective effect, for prevention or treatment of the diseases related to such as NMDA receptors and elevation of calcium anions in cells, including the diseases related to neurodegeneration such as Alzheimer's disease, Parkinson's disease, cerebral paralysis and glaucoma, and the diseases related to cardio-cerebral-vascular system such as Parkinson's syndrome combined with cerebral arteriosclerosis, as well as respiratory tract infections caused by influenza virus.
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- Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases
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A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.
- Liu, Zheng,Yang, Si,Jin, Xiaoyong,Zhang, Gaoxiao,Guo, Baojian,Chen, Haiyun,Yu, Pei,Sun, Yewei,Zhang, Zaijun,Wang, Yuqiang
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p. 135 - 147
(2017/02/05)
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- AMANTADINE NITRATE COMPOUND HAVING A NEUROPROTECTIVE EFFECT AND PREPARATION AND MEDICAL USE THEREOF
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The present invention relates to amantadine nitrate compounds having neural protective effect, and preparation method and medical use thereof. The compounds have the structure of the general formula (I). The compounds have multifunctional mechanisms, including inhibiting NMDA receptors, releasing NO, inhibiting calcium influxes, and having protective effects on cells particularly neurocytes. The compounds can be used in the preparation of medicaments having a cellular protective effect, for prevention or treatment of the diseases related to such as NMDA receptors and elevation of calcium anions in cells, including the diseases related to neurodegeneration such as Alzheimer's disease, Parkinson's disease, cerebral paralysis and glaucoma, and the diseases related to cardio-cerebral-vascular system such as Parkinson's syndrome combined with cerebral arteriosclerosis, as well as respiratory tract infections caused by influenza virus.
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- DUAL MOLECULES CONTAINING A PEROXIDE DERIVATIVE, THEIR SYNTHESIS AND THERAPEUTIC USES
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The invention concerns dual molecules corresponding to formula (I): in which: A represents a molecular residue with antimalarial activity of formula (IIa) or (IIIa) or a residue facilitating bioavailability; B represents a cycloalkyl group potentially substituted, or B represents a bi- or tricyclic group capable of being substituted, or B represents 2 cycloalkyl groups linked together through either a single bond or an alkylene chain; m and n represent independently of one another 0, 1 or 2; R5 represents a hydrogen atom, an alkyl, cycloalkyl or C1-3-alkylene-cycloakyl group; Z1 and Z2 represent an alkyl radical, the group Z1+Z2+Ci+Cj representing a mono- or polycyclic structure, with one of the Z1 or Z2 being able to represent a single bond; R1 and R2, identical or different, represent a hydrogen atom or a functional group capable of increasing hydrosolubility; Rx and Ry forming together a cyclic peroxide including 4 to 8 links and including 1 or 2 additional oxygen atoms in the cyclic structure, possibly substituted by one or more R3 groups; as a base or a salt to be added to an acid, as a hydrate or solvate, in racemic form, isomers and their mixtures, in addition to their diasteroisomers and their mixtures. Preparation method and use as medications with antimalarial activity.
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- Radical addition of alkyl halides to formaldehyde in the presence of cyanoborohydride as a radical mediator. A new protocol for hydroxymethylation reaction
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Hydroxymethylation of alkyl halides was achieved using paraformaldehyde as a radical C1 synthon in the presence of tetrabutylammonium cyanoborohydride as a hydrogen source. The reaction proceeds via a radical chain mechanism involving an alkyl radical addition to formaldehyde to form an alkoxy radical, which abstracts hydrogen from a hydroborate anion.
- Kawamoto, Takuji,Fukuyama, Takahide,Ryu, Ilhyong
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supporting information; experimental part
p. 875 - 877
(2012/02/15)
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- Synthesis and evaluation of dimeric lipophilic iminosugars as inhibitors of glucosylceramide metabolism
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Four dimeric and four monomeric lipophilic iminosugars were synthesized and subsequently evaluated on their inhibitory potential towards mammalian glucosylceramide synthase, glucocerebrosidase, β-glucosidase 2, sucrase and lysosomal α-glucosidase. Compared to their monomeric counterparts the dimeric inhibitors showed decreased inhibition of glucosylceramide synthase and generally a comparable inhibitory potency for the glycosidases.
- Wennekes, Tom,van den Berg, Richard J.B.H.N.,Bonger, Kimberly M.,Donker-Koopman, Wilma E.,Ghisaidoobe, Amar,van der Marel, Gijsbert A.,Strijland, Anneke,Aerts, Johannes M.F.G.,Overkleeft, Herman S.
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experimental part
p. 836 - 846
(2009/10/02)
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- Carbenes in polycyclic systems: Generation and fate of potential adamantane-1,3-dicarbenes
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Potential formation and reactions of adamantane-1,3-dicarbenes 1-3 generated under different conditions and from different precursors, such as sodium salt of adamantane-1,3-dicarbaldehyde ditosylhydrazone (4a), sodium salt of 1,3-diacetyladamantane ditosylhydrazone (5a), sodium salt of 1,3-dibenzoyladamantane ditosylhydrazone (6a), and 1,3-bis(diazobenzyl) adamantane (7) are reported. Carbene species generated thermally from 4a yielded bishomoa-damantane (15), as a final product, via intramolecular insertion into adjacent C - C bond and formation of putative anti-Bredt olefin species, followed by hydrogen abstraction. Pyrolysis of the same sodium salt 4a in the presence of hydrogen donor n-Bu3SnH afforded 1,3-dimethyladamantane (17). Thermal decomposition of sodium salt 5a afforded 1,3-divinyladamantane (14). However, thermal decomposition of sodium salt 6a and diazo-precursor 7 gave benzonitrile as a sole identified product. On the contrary, photolysis of 7 afforded dimeric azine 21. Finally, the synthetic pathways of novel tosylhydrazone derivatives 4, 5, 6 and their corresponding sodium salts, as well as bis-diazocompound 7 are described. Copyright
- Klaic, Lada,Aleskovic, Marija,Veljkovic, Jelena,Mlinaric-Majerski, Kata
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p. 299 - 305
(2008/09/20)
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- NITRATION OR CARBOXYLATION CATALYSTS
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In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1): ???wherein R1and R2represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1and R2may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3;, a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy(e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring. According to such reaction, the substrate can be efficiently nitrated or carboxylated even in a mild or moderate condition.
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- Compositions and methods to prevent toxicity induced by nonsteroidal antiinflammatory drugs
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Nonsteroidal antiinflammatory drugs which have been substituted with a nitrogen monoxide group; compositions comprising (i) a nonsteroidal antiinflammatory drug, which can optionally be substituted with a nitrogen monoxide group and (ii) a compound that directly donates, transfers or releases a nitrogen monoxide group (preferably as a charged species, particularly nitrosonium); and methods of treatment of inflammation, pain, gastrointestinal lesions and/or fever using the compositions are disclosed. The compounds and compositions protect against the gastrointestinal, renal and other toxicities that are otherwise induced by nonsteroidal antiinflammatory drugs.
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- A Chiral Adamantanophane: Preparation, Enantiomer Separation, Theoretical and Experimental Circular Dichroism and Absolute Configuration
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Exchange of aromatic units (e.g. benzene) for aliphatic/alicyclic building blocks (e.g. adamantane) in cyclophanes leads to molecules of the "araliphane" type.The synthesis of the highly strained (1,3)adamantanometacyclophanes 5a-c is described.The cyclophane skeletons of these molecules are conformationally rigid and therefore 5a-c are planar-chiral.The circular dichroism of 5c has been calculated theoretically with NDDO/MRD-CI methods and was measured.Agreement of theory and experiment is good, a comparison of both allows the assignment of the absolute configuration of the two enantiomers of 5c with high probability.Furthermore, analysis of the n?* band in the CD spectrum yields a simple general rule to determine the conformation of the carboxyl group in phenyl ester substructures.Theoretical calculations of the strain energy (Es) of 5c reveal the distribution of strain within the molecule. - Key Words: Adamantanophanes / Calculations, CI / Circular dichroism / Cyclophanes / Strain energy
- Grimme, Stefan,Lemmerz, Ralf,Voegtle, Fritz
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p. 2081 - 2088
(2007/10/02)
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- Adamantane as a Building Block of New Araliphanes - Synthesis, Spectroscopy, and Crystal Structures
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Exchange of benzene units for aliphatic building blocks in cyclophanes leads to new molecules of the "araliphane" type.With adamantane the araliphanes 2 - 4 are synthesized.Their stereochemical behavior as shown by NMR studies and X-ray crystallographic analyses differs significantly from that of their aromatic counterparts.The signals of the intraannular adamantane hydrogens are strongly shifted upfield up to δ = -2.18 (in 2). 4 is obtained as a racemic mixture of enantiomers (in the crystalline state) and shows a boat-like deformation of the benzene moiety.
- Dohm, Joachim,Nieger, Martin,Rissanen, Kari,Voegtle, Fritz
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p. 915 - 922
(2007/10/02)
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