87102-64-5Relevant articles and documents
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).
Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation
Pchelka, Beata Krystyna,Loupy, Andre,Plenkiewicz, Jan,Blanco, Luis
, p. 2719 - 2732 (2007/10/03)
Kinetic resolution of racemic 1-azido-3-aryloxy-2-propanols 1a-g was performed using supported lipase of Candida antarctica-B (Novozym() SP 435) in toluene at 4°C with isopropenyl acetate as the acyl donor to afford the optically active (S)-alcohols 2a-g and their corresponding (R)-acetates 3a-g with E values from 56 to 72. Copyright (C) 2000 Elsevier Science Ltd.
Synthesis and Chromatographic Separation of the Glucuronides of (R)- and (S)-Propranolol
Oatis, J. E.,Baker, J. P.,McCarthy, J. R.,Knapp, D. R.
, p. 1687 - 1691 (2007/10/02)
One of the major metabolites of propranolol (Inderal) is the O-glucuronide.In order to further study its disposition, possible metabolism, and contribution to the antihypertensive effect of propranolol, we have synthesized and separated the two diastereometric propranolol O-β-D-glucuronides (9a,b).These compounds were prepared by reaction of naphthol with epichlorohydrin and treatment of the resulting (2RS)-1'-(2,3-epoxypropoxy)naphthalene (2) with sodium azide to give (2RS)-1-(1'-naphthoxy)-3-azido-2-propanol (3).Alkylation of 3 with methyl (2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranosid)uronate (4) gave methyl (2RS)-uronate (5a,b).Reductive alkylation, followed by HPLC separation of the diastereomers, gave methyl (2R)- and (2S)-uronate (6a,b).Hydrolytic removal of the acetyl and methyl protecting groups gave the free glucuronides, which were then converted to the sodium salts, 9a,b.The stereochemistry of the glycoside linkage was deduced from the 400-MHz 1H NMR spectra.The absolute configuration of the aglycon portion was determined after Glusulase hydrolysis by derivatization with (R)-(+)- or-(-)-α-methylbenzyl isocyanate and comparison of the HPLC retention volumes with those of derivatized reference (R)- and (S)-propranolols.