ChemInform Abstract: Potential Acetylcholinesterase Reactivators: Pyridine and α‐Oxooxime Derivatives.

Daroszewski, Jacek; Serafin, B.; Borkowska, G; Rump, S

doi:10.1002/chin.198717218

Cited by 4 publications

(5 citation statements)

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“…Evaporation of the solvent under reduced pressure afforded crude products which were purified by crystallization from ethanol -ether. Melting points of compounds 3a, 3b, 3c, 4 correspond with those reported in the literature (Ginsburg and Wilson 1957, Daroszewski et al 1986, Hampl et al 1995.…”

Section: Synthetic Partsupporting

confidence: 82%

Synthesis of the three monopyridinium oximes and evaluation of their potency to reactivate acetylcholinesterase inhibited by nerve agents

Kuča¹,

Pícha²,

Cabal³

et al. 2004

JAB

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Three potential reactivators of nerve agents-inhibited acetylcholinesterase: 2-[(hydroxyimino)phenylmethyl]-1-methylpyridinium iodide 3a, 2 -[(hydroxyimino)pyridin-2ylmethyl]-1-methylpyridinium iodide 3b and 2-[(1-hydroxyimino) ethyl]-1-methylpyridinium iodide 3c were synthesized. Their reactivation potency was examined using a standard in vitro reactivation test. A rat brain homogenate was used as the source of acetylcholinesterase. Their reactivation potency was compared with a currently used acetylcholinesterase reactivator -2-PAM (pralidoxime) 4. All tested reactivators were less effective acetylcholinesterase reactivators compared to 2-PAM. In this study, we also tested the reactivation potency of the oxime 2-PAM against inhibition of acetylcholinesterase by sarin, cyclosarin, VX and tabun. Satisfactory results are shown only for the reactivation sarin-and VX-inhibited acetylcholinesterase.

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Section: Synthetic Partsupporting

confidence: 82%

Synthesis of the three monopyridinium oximes and evaluation of their potency to reactivate acetylcholinesterase inhibited by nerve agents

Kuča¹,

Pícha²,

Cabal³

et al. 2004

JAB

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“…(1E,2E)-2,2 -Dipyridylglyoxime (1) was synthesized by the method of Richardson and coworkers [16], which, in contrast to previously reported procedures [12][13][14][15], gives a single isomer of the compound. The synthesis protocol (Scheme 2) involves the reaction of 2,2 -pyridyl with hydroxylammonium chloride in the presence of an excess of sodium hydroxide.…”

Section: Resultsmentioning

confidence: 99%

“…Note that oximes can exist both in the E-and Z-form [13]. In addition, dipyridil glyoxal dioximes and their bisquaternary salts show the ability to reactivate inhibited cholinesterase [14] and their pharmacological activity in vitro and in vivo was tested [15]. Furthermore, dioximes of type I can cyclisize under pressure and in the presence of water to form the corresponding 1,2,5-oxadiazoles (II, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

The crystal structure of (1E,2E)‐2,2′‐dipyridylglyoxime

Sabaté¹,

Delalu²

2011

Heteroatom Chemistry

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1E,2E)-2,2 -dipyridylglyoxime (1) was synthesized by a literature method involving the reaction of 2,2 -pyridyl with an excess of hydroxylammonium chloride and sodium hydroxide in distilled water. 1 was characterized by elemental analysis, melting point, mass spectrometry, and NMR ( 1 H and 13 C) spectroscopy. In addition, the crystal structure of 1 was determined by low temperature X-ray analysis. 1 crystallizes in the monoclinic space group P2 1 /n with four formula units in the unit cell and the following unit cell parameters: a = 6.269(1)Å, b = 10.258(1) A, c = 9.132(1)Å, β = 107.59(1) • , and V = 559.7(1) A 3 . Strong O· · ·N hydrogen bonds link the molecules of 1, forming three-dimensional hydrogen-bonded networks; whereas the unclassical C· · ·O hydrogen bonds result in the formation of C1,1(9) and C2,2(18) infinite chains and dimmer pairs with the graph-set descriptor R2,2(16). Lastly, the structure of 1 was fully optimized using DFT calculations p)) and the NBO and Mulliken charges were calculated at the same level of theory. C 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:59-65, 2012; View this article online at wileyonlinelibrary.com.

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“…All solvent and reagents were used as received, unless otherwise stated. Compound 8 was obtained as previously reported 22…”

Section: Methodsmentioning

confidence: 99%

The Boulton–Katritzky Reaction: A Kinetic Study of the Effect of 5‐Nitrogen Substituents on the Rearrangement of Some (Z)‐Phenylhydrazones of 3‐Benzoyl‐1,2,4‐oxadiazoles

et al. 2014

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The kinetics of the ring‐into‐ring conversion of some new (Z)‐phenylhydrazones of 3‐benzoyl‐1,2,4‐oxadiazole containing different nitrogen‐substituents at C‐5 (3b–d; X = NHMe, NMe2, and NHCOMe) into the relevant triazoles 4b–d have been examined in a wide range of pS+ (0.1–11.9) in 1:1 (v/v) dioxane/water solution. The obtained results have been compared with previous data concerning the (Z)‐phenylhydrazone of 5‐amino‐3‐benzoyl‐1,2,4‐oxadiazole (3a; X = NH2). All of the studied (Z)‐phenylhydrazones rearrange through three different pathways (specific acid‐catalysed, uncatalysed and general base‐catalysed). The different effects of the substituents on the course of the rearrangement in the three pathways have been examined.

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ChemInform Abstract: Potential Acetylcholinesterase Reactivators: Pyridine and α‐Oxooxime Derivatives.

Abstract: The synthesis and pharmacological screening of the pyridine‐2‐carbaldoxime derivatives (I), (IX), and (XII) and of the α‐oxooximes (II) are described.

Cited by 4 publications

References 0 publications

Synthesis of the three monopyridinium oximes and evaluation of their potency to reactivate acetylcholinesterase inhibited by nerve agents

Synthesis of the three monopyridinium oximes and evaluation of their potency to reactivate acetylcholinesterase inhibited by nerve agents

The crystal structure of (1E,2E)‐2,2′‐dipyridylglyoxime

The Boulton–Katritzky Reaction: A Kinetic Study of the Effect of 5‐Nitrogen Substituents on the Rearrangement of Some (Z)‐Phenylhydrazones of 3‐Benzoyl‐1,2,4‐oxadiazoles

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