- PROCESS FOR PREPARING AN ALKOXYMETHYL ALKYNYL ETHER COMPOUND HAVING A TERMINAL TRIPLE BOND
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The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4):H-CtriplebondC(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and "a" represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H-CtriplebondC(CH2)aOH (1), wherein "a" is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.
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Paragraph 0150; 0151; 0153-0157
(2021/06/26)
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- PROCESS FOR PREPARING AN ALKOXYMETHYL ALKYNYL ETHER COMPOUND HAVING A TERMINAL TRIPLE BOND
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The present invention provides a process for preparing an alkoxymethyl alkynyl ether compound having a terminal triple bond of the following formula (4): H—C≡C(CH2)aOCH2OCH2R (4), wherein R represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, and “a” represents an integer of 1 to 10, the method comprising subjecting an alkynol compound having a terminal triple bond of the following formula (1): H—C≡C(CH2)aOH (1), wherein “a” is as defined above, to an alkoxymethylation with a halomethyl alkyl ether compound of the following formula (3): RCH2OCH2X (3), wherein X represents a halogen atom, and R is as defined above, in the presence of a dialkylaniline compound of the following formula (2): [CH3(CH2)b][CH3(CH2)c]NC6H5 (2), wherein b and c represent, independently of each other, an integer of 0 to 9, to form the alkoxymethyl alkynyl ether compound (4) having a terminal triple bond.
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Paragraph 0125; 0126
(2021/07/02)
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- Development of Acidic Imidazolium Ionic Liquids for Activation of Kraft Lignin by Controlled Oxidation: Comprehensive Evaluation and Practical Utility
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A novel, eco-friendly method for the activation of lignin by controlled oxidation was studied. The results obtained for six acidic imidazolium ionic liquids containing the hydrogen sulfate anion were compared. The key goal of this research was to increase the content of carbonyl groups in the lignin structure because these may play the main role in the transport of protons and electrons in active materials for electrochemical applications. By means of a variety of analytical techniques (FTIR, 13C CP/MAS NMR, and X-ray photoelectron spectroscopy; selected reactions to determine the presence of carbonyl groups; SEM; zeta-potential analysis; thermogravimetric analysis/differential thermogravimetric analysis; and porous structure analysis), it was determined that the product obtained after treatment with 3-cyclohexyloxymethy-1-methylimidazolium hydrogen sulfate had favorable properties, in terms of the target application. Electrochemical tests proved that the obtained materials could be used as anodes in lithium batteries. The results show that the activation of lignin with ionic liquids can increase its capacity and maintain stability.
- Klapiszewski, ?ukasz,Szalaty, Tadeusz J.,Kurc, Beata,Stanisz, Ma?gorzata,Zawadzki, Bartosz,Skrzypczak, Andrzej,Jesionowski, Teofil
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p. 361 - 374
(2018/06/04)
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- 6-Biphenylmethyl-3-hydroxypyrimidine-2,4-diones potently and selectively inhibited HIV reverse transcriptase-associated RNase H
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Human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated ribonuclease H (RNase H) remains an unvalidated drug target. Reported HIV RNase H inhibitors generally lack significant antiviral activity. We report herein the design, synthesis, biochemical and antiviral evaluations of a new 6-biphenylmethyl subtype of the 3-hydroxypyrimidine-2,4-dione (HPD) chemotype. In biochemical assays, analogues of this new subtype potently inhibited RT RNase H in low nanomolar range without inhibiting RT polymerase (pol) or integrase strand transfer (INST) at the highest concentrations tested. In cell-based assays, a few analogues inhibited HIV in low micromolar range without cytotoxicity at concentrations up to 100 μM.
- Wang, Lei,Tang, Jing,Huber, Andrew D.,Casey, Mary C.,Kirby, Karen A.,Wilson, Daniel J.,Kankanala, Jayakanth,Parniak, Michael A.,Sarafianos, Stefan G.,Wang, Zhengqiang
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supporting information
p. 680 - 691
(2018/07/29)
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- 3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase
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Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.
- Tang, Jing,Maddali, Kasthuraiah,Metifiot, Mathieu,Sham, Yuk Y.,Vince, Robert,Pommier, Yves,Wang, Zhengqiang
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experimental part
p. 2282 - 2292
(2011/06/17)
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- A systematic study on the activation of simple polyethers by MoCl 5 and WCl6
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MoCl5, 1a, and WCl6, 1b, activate 1,3-dioxolane at room temperature in chlorinated solvents: the compound [MoOCl 3{OC(H)OCH2CH2Cl}]2, 2, has been isolated from MoCl5/dioxolane. The mixed oxo-chloro species WOCl 4, 1c, reacts with 1,3-dioxolane, selectively giving the coordination adduct WOCl4(κ1-C3H6O 2), 3. Dimethoxymethane, CH2(OMe)2, undergoes activation including C-H bond cleavage when reacted with 1a to give the molybdenum complexes [MoOCl3{OC(H)OMe}]2, 4, and Mo 2Cl5(OMe)5, 5. The reactions of 1b with CH 2(OR)2 (R = Me, Et) proceed via O-abstraction with formation of the oxo-derivatives WOCl4[O(R)CH2Cl] (R = Me, 6a; R = Et, 6b) in admixture with equimolar amounts of RCl. The reactions of 1a,b with CMe2(OMe)2 lead to mesityl oxide, MeC(O)CHC(Me)2. A series of simple diethers of general formula ROCH2(CHR′)OR′′ are activated by 1a,b in CDCl 3, usually via cleavage of C-O bonds at high temperature. The complex WCl5(OCH2CH2OMe), 7, has been detected in solution as an intermediate species in the course of the degradation of 1,2-dimethoxyethane (dme) by 1b. The activation of CH(OMe)3 by 1 is limited to C-O bonds and selectively gives methyl chloride and methylformate, which has been found coordinated in WOCl4[OC(H)OMe], 8. The organic fragments produced in the reactions have been detected by GC-MS and NMR analyses, upon hydrolysis of the reaction mixtures. Compounds 2 and 5, which have had their molecular structures ascertained by X-ray diffraction, represent rare examples of crystallographically-characterized dinuclear Mo(v) species containing both halides and oxygen ligands.
- Dolci, Sara,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano
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experimental part
p. 5367 - 5376
(2010/08/04)
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- 3-Alkoxymethyl-1-(1R,2S,5R)-(-)-menthoxymethylimidazolium salts-based chiral ionic liquids
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A new group of imidazolium salt-based chiral ionic liquids have been prepared and characterized. The chiral ionic liquids obtained are stable in air, in contact with water and popular organic solvents. Their physicochemical properties, single-crystal X-ray structures, antimicrobial activities, and antielectrostatic effects have been determined. The chiral ionic liquids synthesized have proven to represent not only potential new solvents in asymmetric synthesis but also effective disinfectants with antielectrostatic activity.
- Feder-Kubis, Joanna,Kubicki, MacIej,Pernak, Juliusz
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experimental part
p. 2709 - 2718
(2011/02/16)
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- Heteropolyacid-catalyzed synthesis of chloromethyl methyl ether
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An efficient (in terms of experiment and time) synthetic procedure for chloromethyl methyl ether (MOM-Cl) is described using heteropolyacids as catalysts.
- Kishore, Pilli Satyananda,Viswanathan, Balasubramanian,Varadarajan, Thirukullam Kanthadai
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p. 429 - 431
(2007/10/03)
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- Simple, rapid procedure for the synthesis of chloromethyl methyl ether and other chloro alkyl ethers
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Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield. Reactions from millimole to mole scale are typically complete in 1-4 h with 0.01 mol % catalyst. The solutions of haloalkyl ethers thus obtained can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess haloalkyl ether is destroyed on workup, thereby minimizing exposure to this class of carcinogenic compounds.
- Berliner, Martin A.,Belecki, Katherine
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p. 9618 - 9621
(2007/10/03)
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- Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group
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A novel class of functionalised cationic surfactant has been obtained. The work-up procedure of synthesis is very simple, the yield is high and the pyridinium salts with alkoxymethyl hydrophobic group are easily purified. All the salts examined showed anti-microbial activities. Some of them exhibited strong activity and wide anti-bacterial spectra similar to the activity of benzalkonium chloride. The relationship between chemical structure and anti-microbial activity was analysed by the QSAR method.
- Pernak, Juliusz,Kalewska, Joanna,Ksycinska, Hanna,Cybulski, Jacek
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p. 899 - 907
(2007/10/03)
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- Process research for the synthesis of RWJ-51204, a novel anxiolytic agent
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RWJ-51204, the lead compound in our pyrido [1,2-α] benzimidazole (PBI) series, was shown to exhibit anxiolytic efficacy in animal models at doses which did not cause central nervous system side effects commonly observed with other anxiolytic agents. To prepare supplies of drug substance for early toxicological and clinical studies, we needed to develop a safe and scaleable synthesis. Our main focus was to improve the last two steps of the process which involved formation of the penultimate carboxamide intermediate followed by alkylation using potentially toxic chloromethyl ethyl ether. Due to safety issues concerning storage and handling of this reagent during the large scale synthesis, we investigated alternate routes to minimize potential exposure risks. The process research carried out for the final steps that led to the safe and cost-effective multi-kilogram synthesis of RWJ-51204 is described herein.
- Cohen, Judith H.,Maryanoff, Cynthia A.,Stefanick, Stephen M.,Sorgi, Kirk L.,Villani Jr., Frank J.
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p. 260 - 265
(2013/09/08)
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- Lower alkoxymethyl esters of 2,4,6-triiodobenzoic acid derivatives
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Esters of certain 2,4,6-triiodobenzoic acid derivatives are useful as X-Ray contrast media. Representative compounds are the ethoxymethyl esters of acetrizoic, iothalamic and iodobenzamic acids.
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