scholarly journals Synthesis of procaine analogues containing pentafluoroethoxy groups in the aromatic nucleus

2021 ◽  
pp. 64-72
Author(s):  
I.I. Gaidarzhy ◽  
◽  
L.A. Motnyak ◽  
B.V. Kunshenko
Keyword(s):  
Mass Spectrometry ◽  
13C Nmr Spectroscopy ◽  
Amino Group ◽  
Ortho Position ◽  
Benzoic Acids ◽  
Anesthetic Activity ◽  
Local Anesthetic Activity ◽  
Structural Analogue ◽  
Benzene Nucleus ◽  
Structural Analogues

In order to synthesize procaine analogs containing one or two pentafluoroethoxy groups, a method for the synthesis of benzoic acids containing a pentafluoroethoxy group in the ortho-position of the benzene nucleus has been developed. An effective method for the synthesis of procaine structural analogues containing one or two pentafluoroethoxy groups has been proposed. It has been shown that the replacement of the amino group by the pentafluoroethoxy group in the procaine molecule leads to a significant increase in the local anesthetic activity of the obtained compounds. The most active compound was a structural analogue of procainamide containing two pentafluoroethoxy groups in positions 2 and 4. The formation of fluorine-containing analogues of procaine was confirmed by 1H, 19F and 13C NMR spectroscopy and mass spectrometry.

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

Acridine Synthesis by the Reaction of 2-(Perfluoroalkyl)aniline with ortho-Alkyl-Substituted Aromatic Grignard Reagent: Mechanistic Studies

2015 ◽  
Vol 68 (2) ◽  
pp. 196
Author(s):  
Lucjan Strekowski ◽  
Jianguo Zhang ◽  
Jaroslaw Saczewski ◽  
Ewa Wolinska
Keyword(s):  
Mass Spectrometry ◽  
Grignard Reagent ◽  
Fast Atom Bombardment ◽  
Ortho Position ◽  
Mechanistic Studies ◽  
Ethyl Group ◽  
Electron Impact Mass ◽  
Perfluoroalkyl Group ◽  
First Time ◽  
Impact Mass

The reaction of 2-(perfluoroethyl)aniline and its higher perfluoroalkyl analogues with an arylmagnesium bromide substituted with a methyl or ethyl group at the ortho position furnishes an acridine containing a shorter perfluoroalkyl group at the 9-position and devoid of the methyl or ethyl group of the Grignard reagent. Yields are in the range of 46–93 %. The intermediary of a substituted aza-ortho-xylylene has been postulated for related transformations in the literature previously, but this intermediate product has never been isolated. As part of this work, the labile product E-27 (half-life of 6 h at 23°C) was isolated for the first time and characterized by infrared spectroscopy, electron impact mass spectrometry, fast atom bombardment mass spectrometry, and 1H NMR. Experimental evidence was also obtained regarding the elimination of the ortho-alkyl group of the Grignard reagent during the course of the reaction as an alcohol.

ChemInform Abstract: SYNTHESIS AND LOCAL ANESTHETIC ACTIVITY OF 6-(Ω-AMINO-Ω-ARYLALKYL)BENZO-1,4-DIOXANES

1985 ◽  
Vol 16 (17) ◽  
Author(s):  
V. K. DAUKSHAS ◽  
YU. YU. RAMANAUSKAS ◽  
E. B. UDRENAITE ◽  
A. B. BRUKSHTUS ◽  
V. V. LAPINSKAS ◽  
...  
Keyword(s):  
Local Anesthetic ◽  
Anesthetic Activity ◽  
Local Anesthetic Activity

scholarly journals Mechanism of Intrinsic Resistance to Vancomycin in Clostridium innocuum NCIB 10674

2004 ◽  
Vol 186 (11) ◽  
pp. 3415-3422 ◽  
Author(s):  
Véronique David ◽  
Bülent Bozdogan ◽  
Jean-Luc Mainardi ◽  
Raymond Legrand ◽  
Laurent Gutmann ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Pressure ◽  
Amino Group ◽  
Intrinsic Resistance ◽  
Chromosomal Fragment ◽  
High Affinity ◽  
C Terminus ◽  
Low Levels ◽  
Enterococcus Gallinarum ◽  
Level Resistance

ABSTRACT We have studied the basis for intrinsic resistance to low levels of vancomycin in Clostridium innocuum NCIB 10674 (MIC = 8 μg/ml). Analysis by high-pressure liquid chromatography (HPLC) and mass spectrometry of peptidoglycan nucleotide precursors pools revealed the presence of two types of UDP-MurNac-pentapeptide precursors constitutively produced, an UDP-MurNAc-pentapeptide with a serine at the C terminus which represented 93% of the pool and an UDP-MurNAc-pentapeptide with an alanine at the C terminus which represented the rest of the pool. C. innocuum cell wall muropeptides containing pentapeptide[Ser], either dialanine substituted on the epsilon amino group of lysine or not, were identified and represented about 10% of the monomers while only 1% of pentapeptide[d-Ala] monomers were found. The sequence of a 2,465-bp chromosomal fragment from C. innocuum was determined and revealed the presence of ddlc. innocuum and C. innocuum racemase genes putatively encoding homologues of d-Ala:d-X ligases and amino acid racemases, respectively. Analysis of the pool of precursors of Enterococcus faecalis JH2-2, containing cloned ddlc. innocuum and C. innocuum racemase genes showed in addition to the UDP-MurNAc-pentapeptide[d-Ala], the presence of an UDP-MurNAc-pentapeptide[d-Ser] precursor. However, the expression of low-level resistance to vancomycin was observed only when both genes were cloned in E. faecalis JH2-2 together with the vanXYc gene from Enterococcus gallinarum BM4174 which encodes a d,d-peptidase which eliminates preferentially the high affinity vancomycin UDP-MurNAc-pentapeptide [d-Ala] precursors produced by the host. We conclude that resistance to vancomycin in C. innocuum NCIB 10674 was related to the presence of the two chromosomal ddlc. innocuum and C. innocuum racemase genes allowing the synthesis of a peptidoglycan precursor terminating in serine with low affinity for vancomycin.

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