- Pseudorotaxane capped mesoporous silica nanoparticles for 3,4-methylenedioxymethamphetamine (MDMA) detection in water
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Mesoporous silica nanoparticles loaded with fluorescein and capped by a pseudorotaxane, formed between a naphthalene derivative and cyclobis(paraquat-p-phenylene) (CBPQT4+), were used for the selective and sensitive fluorogenic detection of 3,4-methylenedioxymethamphetamine (MDMA).
- Lozano-Torres, Beatriz,Pascual, Lluís,Bernardos, Andrea,Marcos, María D.,Jeppesen, Jan O.,Salinas, Yolanda,Martínez-Má?ez, Ramón,Sancenón, Félix
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Read Online
- OXIME ESTER COMPOUND AND POLYMERIZATION INITIATOR COMPRISING THE COMPOUND
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PROBLEM TO BE SOLVED: To provide a novel compound that has low sublimability and serves as a polymerization initiator with high sensitivity that absorbs near-ultraviolet light of e.g. 365 nm to be activated, and a polymerization initiator and a photosensitive composition prepared with the compound. SOLUTION: The present invention provides a novel oxime ester compound represented by formula (I) and a polymerization initiator prepared with the compound (R1 is a cyclopentylmethyl methyl group or the like; R2 is a methyl group or the like; R3-R6, R8, and R9 are each H or the like; and R7 is a methoxy group or the like). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0105-0107
(2018/08/25)
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- Different Steric-Twist-Induced Ternary Memory Characteristics in Nonconjugated Copolymers with Pendant Naphthalene and 1,8-Naphthalimide Moieties
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Herein, novel random copolymers PMNN and PMNB were designed and synthesized, and the memory devices Al/PMNN and PMNB/ITO both exhibited ternary memory performance. The switching voltages of the OFF–ON1 and ON1–ON2 transitions for both memory devices are around ?2.0 and ?3.5 V, respectively, and the ON1/OFF, ON2/ON1 current ratios are both up to 103. The observed tristable electrical conductivity switching could be attributed to field-induced conformational ordering of the naphthalene rings in the side chains, and subsequent charge trapping by 1,8-naphthalimide moieties. More interestingly, by adjusting the connection sites of 1,8-naphthalimide moieties to tune the steric-twist effect, different memory properties were achieved (PMNN showed nonvolatile write once, read many (WORM) memory behavior, whereas PMNB showed volatile static RAM (SRAM) memory behavior). This result will offer a guideline for the design of different high-performance multilevel memory devices by tuning the steric effects of the chemical moieties.
- Wang, Ming,Li, Zhuang,Li, Hua,He, Jinghui,Li, Najun,Xu, Qingfeng,Lu, Jianmei
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supporting information
p. 2744 - 2748
(2017/10/07)
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- Indane derivative and synthetic method and medicinal application thereof
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The invention discloses an indane derivative and a synthetic method and medicinal application thereof. The structural general formula is as shown in the specification. The indane derivative disclosed by the invention has excellent inhibitory activity and high selectivity on MAO-B.
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Paragraph 0056; 0057; 0058
(2017/09/02)
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- Activity of Fluorine-Containing Analogues of WC-9 and Structurally Related Analogues against Two Intracellular Parasites: Trypanosoma cruzi and Toxoplasma gondii
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Two obligate intracellular parasites, Trypanosoma cruzi, the agent of Chagas disease, and Toxoplasma gondii, an agent of toxoplasmosis, upregulate the mevalonate pathway of their host cells upon infection, which suggests that this host pathway could be a potential drug target. In this work, a number of compounds structurally related to WC-9 (4-phenoxyphenoxyethyl thiocyanate), a known squalene synthase inhibitor, were designed, synthesized, and evaluated for their effect on T. cruzi and T. gondii growth in tissue culture cells. Two fluorine-containing derivatives, the 3-(3-fluorophenoxy)- and 3-(4-fluorophenoxy)phenoxyethyl thiocyanates, exhibited half-maximal effective concentration (EC50) values of 1.6 and 4.9 μm, respectively, against tachyzoites of T. gondii, whereas they showed similar potency to WC-9 against intracellular T. cruzi (EC50values of 5.4 and 5.7 μm, respectively). In addition, 2-[3- (phenoxy)phenoxyethylthio]ethyl-1,1-bisphosphonate, which is a hybrid inhibitor containing 3-phenoxyphenoxy and bisphosphonate groups, has activity against T. gondii proliferation at sub-micromolar levels (EC50=0.7 μm), which suggests a combined inhibitory effect of the two functional groups.
- Chao, María N.,Li, Catherine,Storey, Melissa,Falcone, Bruno N.,Szajnman, Sergio H.,Bonesi, Sergio M.,Docampo, Roberto,Moreno, Silvia N. J.,Rodriguez, Juan B.
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p. 2690 - 2702
(2016/12/23)
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- Synthesis and inhibitory evaluation of 3-linked imipramines for the exploration of the S2 site of the human serotonin transporter
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The human serotonin transporter is the primary target of several antidepressant drugs, and the importance of a primary, high affinity binding site (S1) for antidepressant binding is well documented. The existence of a lower affinity, secondary binding site (S2) has, however, been debated. Herein we report the synthesis of 3-position coupled imipramine ligands from clomipramine using a copper free Sonogashira reaction. Ligand design was inspired by results from docking and steered molecular dynamics simulations, and the ligands were utilized in a structure-activity relationship study of the positional relationship between the S1 and S2 sites. The computer simulations suggested that the S2 site does indeed exist although with lower affinity for imipramine than observed within the S1 site. Additionally, it was possible to dock the 3-linked imipramine analogs into positions which occupy the S1 and the S2 site simultaneously. The structure activity relationship study showed that the shortest ligands were the most potent, and mutations enlarging the proposed S2 site were found to affect the larger ligands positively, while the smaller ligands were mostly unaffected.
- Brink?, Anne,Larsen, Maja T.,Kolds?, Heidi,Besenbacher, Louise,Kolind, Anders,Schi?tt, Birgit,Sinning, Steffen,Jensen, Henrik H.
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supporting information
p. 2725 - 2738
(2016/06/08)
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- Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers
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A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is
- Liu, Yajun,Park, Se Kyung,Xiao, Yan,Chae, Junghyun
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supporting information
p. 4747 - 4753
(2014/06/24)
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- IRREVERSIBLE COVALENT INHIBITORS OF THE GTPASE K-RAS G12C
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Irreversible inhibitors of K-Ras, H-Ras or N-ras protein comprising a G12C mutation are provided. Also disclosed are methods to regulate the activity of K-Ras, H-Ras or N-ras protein comprising G12C mutation and methods to disease mediated by K-Ras, H-Ras or N-ras G12C.
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Page/Page column 70
(2014/09/29)
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- Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions
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Starting from cyclohexanone derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. The process was also used with tetralone derivatives and polyols. Several reactions were performed to propose a mechanism for this transformation. The formation of an enol ether followed by a dehydrogenation reaction seem to be the key steps of this reaction. Aryl ethers were prepared in good yields and with good selectivities in a solvent-free and heterogeneous catalytic dehydrogenative alkylation of cyclohexanones with various alcohols. Three different complementary routes were used, and for the first time, non-aerobic, safe conditions could be used. Moreover, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. Copyright
- Sutter, Marc,Lafon, Romain,Raoul, Yann,Metay, Estelle,Lemaire, Marc
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supporting information
p. 5902 - 5916
(2013/09/23)
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- High refractive index pressure-sensitive adhesives
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The present invention provides pressure-sensitive adhesives having a refractive index of at least 1.48. The pressure-sensitive adhesives comprise at least one monomer containing a substituted or an unsubstituted aromatic moiety.
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Page/Page column 7
(2010/02/14)
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- Structure-affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101
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A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the α1a-AR with respect to the other two α1 subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the α1a-AR, α1b-AR, α1d-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific α1a affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high α1a affinity of (S)-1 and its α1a versus α1b selectivity slightly increasing the α1a/α1d and α1a/5HT 1A affinity ratios. The SAR data were evaluated in the light of known α1 subtype pharmacophores and of the α1a-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models.
- Bolchi, Cristiano,Catalano, Paolo,Fumagalli, Laura,Gobbi, Marco,Pallavicini, Marco,Pedretti, Alessandro,Villa, Luigi,Vistoli, Giulio,Valoti, Ermanno
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p. 4937 - 4951
(2007/10/03)
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- A new route to amino-2-propanol structures with adrenergic β-blocker activity using low valent titanium
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Amino-2-propanol structures can be obtained by addition to dibenzyl acetals of in situ generated dihalocarbenes using LTV (Low Valent Titanium). This methodology can be used to obtain adrenergic β-blockers with amino-2-propanol structure. Tetrahalomethane are the best dihalocarbene precursors. The yields obtained using halofluromethanes can be increased by addition of carbontetrachloride. A process that can imply halogen transfer may be proposed.
- Bermudez,Del Campo,Sinisterra,Llama
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p. 4137 - 4140
(2007/10/03)
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- 2-(1-naphthyloxy)ethylamines with enhanced affinity for human 5-HT(1Dβ) (h5-HT(1B)) serotonin receptors
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Although the β-adrenergic antagonist propanolol (1) binds at rodent 5- HT(1B) serotonin receptors, it displays low affinity (K(i) > 10 000 nM) for its species homologue 5-HT(1DB) (i.e., h5-HT(1B)) receptors. The structure of propanolol was systematically modified in an attempt to enhance its affinity for the latter population of receptors. Removal of the alkyl hydroxyl group, shortening of the O-alkyl chain from three to two methylene groups, and variation of the terminal amine substituent resulted in compounds, such as N- monomethyl-2-(1-naphthyloxy)-ethylamine (11; K(i) = 26 nM), that display significantly higher h5-HT(1B) affinity than propanolol. Compound 11 was shown to bind equally well at human 5-HT(1Dα) (h5-HT(1D) receptors (K(i) = 34 nM) and was further demonstrated to possess h5-HT(1B) agonist character in an adenylate cyclase assay. It would appear that such (aryloxy)alkylamines may represent a novel class of 5-HT(1D) receptor agonists.
- Ismaiel,Dukat,Law,Kamboj,Fan,Lee,Mazzocco,Buekschkens,Teitler,Pierson,Glennon
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p. 4415 - 4419
(2007/10/03)
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- Synthesis of 5'-polyarene-tethered oligo-DNAs and the thermal stability and spectroscopic properties of their duplexes and triplexes
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Eleven different planar hydroxy alkylated polyarenes 1-11 with different geometry, bulk and electronic characteristics were synthesised, and used for tethering to the 5'-phosphate of a 9-mer and a 18-mer DNA sequences through solid-phase synthesis. The 5'-polyarene-tethered 9-mers 30-40 were tested for their ability to form stable duplexes with four complementary target DNA-strands 25-28 of different length. The 5'-polyarene-tethered 18-mers 44-54 were tested for their ability to form stable triplexes with a 24-mer duplex target 41+42. The T(m) measurements of duplexes at low salt and pH 7.3 showed that the angular nitro phenanthrene and phenanthrene conjugates 31 and 30 gave the highest duplex stabilisations with targets 25 (ΔT(m) 13.8°C and 11.8°C) and 26 (ΔT(m), 12.3°C and 11.9°C). With the mismatch sequence 28, only 30 and 31 gave a high ΔT(m), of 11.6°C and 10.8°C respectively, while lower ΔT(m), values were observed for other conjugates (ΔT(m), -4.0-5.0°C). The T(m) measurements of triplexes between 43-54 and duplex target 41+42 at low salt and pH 7.3, 6.5 and 6.0 without Mg2+ showed that the nitro phenanthrene conjugate 45 gave the best triplex stabilisation (ΔT(m), 4.1-5.4°C). The stabilisation of nitro phenanthrene conjugate 45 compared to phenanthrene conjugate 44 increased more remarkably when Mg2+ was present: 45 (ΔT(m), 15°C), 44 (ΔT(m), 10°C). These results imply that the electron density of the chromophore influences the π-π stacking interactions between the chromophore and nucleobases, and thereby influencing the duplex and triplex stability. Fluorescence measurements on single strand to double strand transition indicated that the 5'-tethered polyarenes are stacked only on the neighbouring nucleobases of the opposite strand. In case of 5'-9-N-ethylphenazinium conjugate 36, a comparative NMR and fluorescence measurement has unambiguously shown that the tethered phenazinium ion is indeed intercalated between the nucleotides of the opposite target strand 26. Thermodynamic calculations showed the most stable ΔG°(298K) for 30, 31(+targets 25, 26, 28) and 35, 36(+targets 25, 26) compared to the blank 29 ΔΔG°(298K) ~-10kJ mol-1). The non-palindromic target 27 was shown by T(m) measurements to form a stable tertiary structure, which was very little affected by addition of any 5'-tethered conjugate, thereby showing the importance of the tertiary structures of an in vivo antisense target and its implication in regard to its bioavailablity to complementary antisense probes.
- Puri, Nitin,Zamaratski, Edouard,Sund, Christian,Chattopadhyaya, Jyoti
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p. 10409 - 10432
(2007/10/03)
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- Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3'-azido-3'-deoxythymidine
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A series of new ether lipid-3'-azido-3'-deoxythymidine (AZT) conjugates (11a-g) were synthesized and evaluated for anti-HIV activity. The effect of chirality on the antiviral activity was examined through the synthesis of AZT conjugates bearing alkoxypropanols in the lipid portion of the molecule (11a-d). In addition, the long alkyl chain of alkoxyethyl ether lipid-AZT analogs was replaced with aromatic groups (11e-g), and the effect of this structural modification on activity is reported. The results of the biological tests indicate that analogs with a methyl group α to the phosphate moiety (11c,d) exhibit a marked degree of stereoselectivity with regard to their anti-HIV activity. Also, replacement of the long alkyl chain with aromatic groups in the oxyalkyl ether phospholipid-AZT conjugates leads to substantially more potent compounds (11e-g) with an anti-HIV activity comparable to that of AZT.
- Tsotinis, Andrew,Calogeropoulou, Theodora,Koufaki, Maria,Souli, Charikleia,Balzarini, Jan,De Clercq, Erik,Makriyannis, Alexandros
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p. 3418 - 3422
(2007/10/03)
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- Pyridinium derivatives, their production and use
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Novel pyridinium derivatives represented by the formula (I): STR1 wherein STR2 is an optionally substituted pyridinium ring; R1 is a lower alkyl group or aralkyl group; R7 and R10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group; l is 0 or 1; R5 is a phenylene group or an alkylene group which may be substituted; R11 is an alkyl group or aryl group; X is a group of the formula: --CH2 OCH2 -- or a group of the formula: STR3 wherein R6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3; U is a group of the formula: STR4 wherein R4 is hydrogen, a lower alkyl group, aryl group or aralkyl group; Y and Z are independently a divalent chain group consisting of one to six members which is selected from the class consisting of groups of the formulae: STR5 wherein R is hydrogen, a lower alkyl group, acyl group or aryl group and at least one of which is a group of the formula: STR6 with the proviso that R may be the same or different from each other, or may form a ring together when two or more groups of the formula: STR7 are present, that R may be bonded to R4 when Y contains a group of the formula: STR8 and that R may be bonded to R11 when Z contains a group of the formula: STR9 and W? is a counter anion; are useful as a platelet activating factor antagonist.
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