208244-48-8Relevant academic research and scientific papers
Broadening the chemical scope of laccases: Selective deprotection of N-benzyl groups
Martínez-Montero, Lía,Díaz-Rodríguez, Alba,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information, p. 2794 - 2798 (2015/05/27)
Laccase from Trametes versicolor together with TEMPO has been found to be a very efficient system to deprotect N-benzylated primary amines, differing from previously described methods since it uses oxygen as a mild oxidant in aqueous medium. Chemoselective removal of the benzyl group was achieved with excellent yields when secondary amines and alcohol moieties were also present.
Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds
Sasano, Yusuke,Nagasawa, Shota,Yamazaki, Mai,Shibuya, Masatoshi,Park, Jaiwook,Iwabuchi, Yoshiharu
supporting information, p. 3236 - 3240 (2014/04/03)
The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.
Acid promoted cyclodehydration of amino alcohols with amide acetal
Hwang, Soonho,Park, Heemin,Kwon, Yongseok,Kim, Sanghee
, p. 60017 - 60024 (2015/02/19)
A convenient acid-promoted cyclization protocol for the formation of azaheterocycles from amino alcohols is described. The reaction involves the use of N,N-dimethylacetamide dimethyl acetal (DMADA) as the activating reagent of the hydroxyl group. Using this protocol, pyrrolidines or piperidines with various substituents can be synthesized in good to high yields.
Benzo-21-crown-7/secondary dialkylammonium salt [2]pseudorotaxane- and [2]rotaxane-type threaded structures
Zhang, Chuanju,Li, Shijun,Zhang, Jinqiang,Zhu, Kelong,Li, Ning,Huang, Feihe
, p. 5553 - 5556 (2008/09/17)
We demonstrate that secondary dialkylammonium salts can thread through the cavity of benzo-21-crown-7 to form [2]pseudorotaxanes with binding constants (527-1062 M-1 in acetone) higher than the corresponding values (135-261 M-1 in acetone) of the analogous complexes with their traditionally used host, dibenzo-24-crown-8. Based on this new benzo-21-crown-7/secondary dialkylammonium salt recognition motif, a [2]rotaxane was successfully prepared. The formation of these threaded structures was confirmed by proton NMR spectroscopy, electrospray ionization mass spectrometry, and X-ray single crystal analysis.
New anti-HIV derivatives: Synthesis and antiviral evaluation
De Michelis,Rocheblave,Priem,Chermann,Kraus
, p. 1253 - 1262 (2007/10/03)
A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT4 cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC50 values for compounds (31, 40, 34, 37 and 46Scheme 3(i) Na2SO4, CH2Cl2, rt; (ii) NaBH4, EtOH, 0°C; (iii) Boc2O, CH2Cl2, 0°C; (iv) DMSO, TFAA, Et3N, CH2Cl2, -60°C; (v) TFA, CH2Cl2, rt; (vi) BOP, RCOOH, Et3N, CH2Cl2, rt.) range from 0.1 to 1μM. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. Copyright (C) 2000 Elsevier Science Ltd.
Synthesis and anti-HIV evaluation of new 2',3'-dideoxy-3'-thiacytidine prodrugs
Mourier, Nicolas,Camplo, Michel,Della Bruna, Giovanna Schioppacassi,Pellacini, Francesco,Ungheri, Domenico,Chermann, Jean-Claude,Kraus, Jean-Louis
, p. 1057 - 1091 (2007/10/03)
A series of anti-HIV prodrugs possessing various polyaminated side arms have been developed. The incorporation of a N-Boc protected monoamine or diamine side arm into the backbone of the 2',3'-dideoxy-3'-thiacytidine 1 (BCH-189) provided an increase in antiviral potency, which could be several orders magnitude greater than the parent drug (1) depending on the cell culture systems used (MT-4 or MDMs). Twenty six 2',3'-dideoxy-3'-thiacytidine prodrugs which differ from each other by the length, the nature of the 5'-O function and the 5'-O or/and N-4 position on the nucleoside moiety were synthesized. Among this new series of prodrugs, several congeners (12c and 12a) were found to inhibit HIV-1 replication in cell culture with 50% effective concentrations EC50 of 10 and 50 nM respectively, in MT-4 cells. Compound 12c was found more active on infected MDMs cells with 50% effective concentration of 0.01 nM. The synthesis and the antiviral properties of these compounds are discussed.
