2186-25-6Relevant academic research and scientific papers
Tandem H/D Exchange-SET Reductive Deuteration Strategy for the Synthesis of α,β-Deuterated Amines Using D2O
An, Jie,Ding, Yuxuan,Li, Ke,Ling, Chen,Luo, Shihui,Ma, Yuan,Qin, Zixuan,Weng, Chaoqun,Zhao, Tianxiao
, p. 11862 - 11870 (2021)
α,β-Deuterated amines are crucial for the development of deuterated drugs. We intend to introduce the novel tandem H/D exchange-single electron transfer (SET) reductive deuteration strategy with high pot- and reagent-economy by the synthesis of α,β-deuterated amine using nitrile as the precursor. The H/D exchange of the -CH2CN group was achieved by D2O/Et3N, which were also the required reagents in the tandem SmI2-mediated SET reductive deuteration of the α-deuterated nitrile. The potential application of this method was further showcased by the synthesis of bevantolol-d4.
Facile microwave-assisted synthesis and antitubercular evaluation of novel aziridine derivatives
Sarojini, Perumal,Jeyachandran, Malaichamy,Sriram, Dharmarajan,Ranganathan, Palraj,Gandhimathi
, (2021/02/26)
Novel 2-(aryloxymethyl)aziridines and 2-((3-aryl-1-phenylallyloxy)methyl)aziridine derivatives were prepared via ring-opening reaction of epoxides. The synthesized derivatives were characterized by using elemental analysis (EA), FT-IR, 13C NMR, and 1H NMR. The in vitro antitubercular activities of the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB H37Rv) strain using MTT-MABA assay. All the aziridine derivatives exhibited improved persuasive antitubercular activity against MTB H37Rv in comparison with standard drugs. Among the tested compounds, 2-(naphthalene-1-yloxy) methyl aziridine (5b), 2-(naphthalene-2-yloxy)methylaziridine (5c), 2-(m-tolyloxymethyl)aziridine (5e), 2-(3-(4-methoxyphenyl)-1-phenylalloxy)methylaziridine (12b) and 2-(3-(2-chlorophenyl)-1-phenylallyloxy)methylaziridine (12c) revealed promising activity against MTB H37Rv. Specifically, compound 5b and 12 b showed three-times more active (MIC = 0.5 μg/mL) than the standard drugs ethambutol (MIC = 1.56 μg/mL) and ciprofloxacin (MIC = 1.56 μg/mL).
NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b] [1,4]oxathiin-3-yl)methanols from aryloxymethylthiiranes
Dong, Jun,Xu, Jiaxi
, p. 9037 - 9044 (2018/06/08)
(2,3-Dihydrobenzo[b][1,4]oxathiin-3-yl)methanols were synthesized via reactions of aryloxymethylthiiranes and N-bromosuccinimide (NBS) in DMSO under microwave irradiation. The reaction mechanism was proposed as an intramolecular aromatic electrophilic substitution of 1-bromo-2-(aryloxymethyl)thiiran-1-iums, generated from aryloxymethylthiiranes and NBS, and the subsequent DMSO nucleophilic ring opening reaction of thiiran-1-iums followed by the water displacement. The current method provides a direct and simple strategy in the efficient preparation of (2,3-dihydrobenzo[b][1,4]oxathiin-3-yl)methanols from readily available aryloxymethylthiiranes.
Facile synthesis of thietanes via ring expansion of thiiranes
Dong, Jun,Xu, Jiaxi
, p. 836 - 844 (2017/02/05)
Thietanes are pharmaceutically important cores of some biological compounds and intermediates of organic synthesis. Various thietanes were prepared from thiiranes via ring expansion through a reaction with trimethyloxosulfonium iodide in the presence of sodium hydride. The reaction process is a nucleophilic ring-opening reaction of thiiranes with dimethyloxosulfonium methylide, generated from trimethyloxosulfonium iodide and sodium hydride, and subsequent intramolecular displacement (cyclization) of thiolates to the dimethyloxosulfonium moiety. The current method provides a new strategy for efficient preparation of thietanes from readily available thiiranes.
AROMATIC GLYCOL ETHERS AS WRITING MONOMERS IN HOLOGRAPHIC PHOTOPOLYMER FORMULATIONS
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Paragraph 0160; 0161; 0162; 0163; 0164; 0165, (2017/04/11)
The invention relates to a photopolymer formulation comprising specific aromatic glycol ethers as writing monomers, matrix polymers and a photoinitiator. The invention further provides an unexposed holographic medium obtainable using an inventive photopolymer formulation, and an exposed holographic medium obtainable by exposing a hologram into an inventive unexposed holographic medium. The invention likewise provides a visual display comprising an inventive exposed holographic medium, for the use of an inventive exposed holographic medium for production of chip cards, identification documents, 3D images, product protection labels, labels, banknotes or holographic optical elements, and specific aromatic glycol ethers.
The effective direct resolution procedure for the chiral drug bevantolol hydrochloride
Bredikhina, Zemfira A.,Antonovich, Olga A.,Zakharychev, Dmitry V.,Bredikhin, Alexander A.
, p. 397 - 403 (2016/05/19)
The solubility of the chiral drug bevantolol hydrochloride 1 in water and the azeotropic mixture ethanol-water has been investigated. It was found that rac-1 meets the requirements of Meyerhoffer's rule, so it was possible to reduce the ternary diagram, describing the solubility of 1, to a pseudo binary form, which facilitates the analysis of crystallization processes caused by temperature changes. On this basis, the effective and robust resolution procedure of racemic bevantolol hydrochloride by a preferential crystallization approach has been realized successfully.
DIMETHOXYPHENYL INHIBITORS OF VESICULAR MONOAMINE TRANSPORTER 2
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Paragraph 00173, (2016/09/15)
Described are dimethoxyphenyl inhibitors of VMAT2, pharmaceutical compositions thereof, and methods of use thereof.
Synthesis and evaluation of 4-(2-hydroxypropyl)piperazin-1-yl) derivatives as Hsp90 inhibitors
Cherfaoui, Bahidja,Guo, Tian-Kun,Sun, Hao-Peng,Cheng, Wei-Lin,Liu, Fang,Jiang, Fen,Xu, Xiao-Li,You, Qi-Dong
supporting information, p. 2423 - 2432 (2016/05/24)
We previously reported 4-(3-((6-bromonaphthalen-2-yl)oxy)-2-hydroxypropyl)-N,N-dimethylpiperazine-1-sulfonamide (1) as a novel heat shock protein 90 inhibitor with moderate activity. In our ongoing efforts for the discovery of Hsp90 modulators we undertake structural investigations on 1. Series of the titled compound were designed, synthesized and evaluated. We have found that compounds with a hydroxyl group at C-4 of the aryl ring on the piperazine moiety possess Hsp90 inhibition properties. Compound 6f with improved activity could be further developed and optimized as Hsp90 inhibitor.
Bevantolol drug intermediate 3-m-tolyloxy-1, 2-epoxypropane synthetic method
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Paragraph 0014-0015, (2017/02/17)
A bevantolol drug intermediate 3-m-tolyloxy-1, 2-epoxypropane synthetic method comprises the following steps: 0.61mol of m-cresol, 0.71mol of a potassium hydrogen sulfite solution and 0.16mol of propionitrile are added into a reaction vessel provided with a stirrer, a reflux condenser and dropping funnel, stirring speed is controlled at 130-170rpm, 1.3-1.5mol of epoxy aminopropane propylene are slowly added, the dropwise addition time is controlled in 90-120min, the solution temperature is raised to 60-65 DEG C, the solution is stirred for 4-5h, extracted for 3-5 times with nitromethane, washed with a saline solution, dehydrated with a dehydrating agent, washed with toluene, and recrystallized in cyclohexane to obtain crystal 3-m-tolyloxy-1,2-epoxypropane.
THERAPEUTIC COMPOUNDS
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Paragraph 00118; 00125, (2015/02/02)
The present invention relates to therapeutic compounds useful for the treatment of neurodegenerative and neuromuscular diseases and/or triplet repeat diseases (e.g. Friedreich's ataxia). The compounds have the structural formula I shown below: wherein Q, X, p, R1, q, R3 and R4 are as defined herein. The present invention also relates to pharmaceutical compositions comprising the compounds defined herein, the use of these compositions for the treatment of neurodegenerative and neuromuscular diseases and/or triplet repeat diseases (e.g. Friedreich's ataxia), and to processes for the preparation of the pharmaceutical compositions defined herein.
