Selenophosphorus Compounds as Powerful Cholinesterase Inhibitors

Åkerfeldt, Stig; Fagerlind, Lars.

doi:10.1021/jm00313a032

Cited by 16 publications

(11 citation statements)

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“…Reaction with Selenium Nucleophiles. The reactions of selenium nucleophiles are similar to those of the sulfur nucleophiles: selenophosphates can be aminoalkylated (135). A dihydroselenazine has been obtained by reaction of diethyl ketone, elementary selenium, and ethyleneimine (136).…”

Section: Reaction With Nitrogenmentioning

confidence: 96%

Imines, Cyclic

Scherr¹,

Steuerle²,

Fikentscher³

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Section: Reaction With Nitrogenmentioning

confidence: 96%

Imines, Cyclic

Scherr¹,

Steuerle²,

Fikentscher³

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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“…Class 2 are the phosphorylated thiocholines (or phosphorylated analogs of class 1), such as the VG. Classes 3 and 4 encompass the phosphonylated and phosphorylated selenocholines, respectively, which are more toxic than their sulfur analogs; however, they are likely not of military importance since they are easily decomposed in the presence of air and release elemental selenium [12]. Class 5 includes V-agents that contain a thiocholine-like moiety (-SCH 2 CH 2 SCH 2 CH 3 ), while V-agents belonging to classes 6 and 7 do not contain a choline moiety at all.…”

Section: General Structures and (Sub)categories Of V-agentsmentioning

confidence: 99%

Chemical, Physical, and Toxicological Properties of V-Agents

Pampalakis

Kostoudi

2023

IJMS

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V-agents are exceedingly toxic organophosphate nerve agents. The most widely known V-agents are the phosphonylated thiocholines VX and VR. Nonetheless, other V-subclasses have been synthesized. Here, a holistic overview of V-agents is provided, where these compounds have been categorized based on their structures to facilitate their study. A total of seven subclasses of V-agents have been identified, including phospho(n/r)ylated selenocholines and non-sulfur-containing agents, such as VP and EA-1576 (EA: Edgewood Arsenal). Certain V-agents have been designed through the conversion of phosphorylated pesticides to their respective phosphonylated analogs, such as EA-1576 derived from mevinphos. Further, this review provides a description of their production, physical properties, toxicity, and stability during storage. Importantly, V-agents constitute a percutaneous hazard, while their high stability ensures the contamination of the exposed area for weeks. The danger of V-agents was highlighted in the 1968 VX accident in Utah. Until now, VX has been used in limited cases of terrorist attacks and assassinations, but there is an increased concern about potential terrorist production and use. For this reason, studying the chemistry of VX and other less-studied V-agents is important to understand their properties and develop potential countermeasures.

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“…In fact the pre-halogen nonmetals share more distinctive properties than any other class of elements. While the noble gases, as elemental substances, can be characterized by their invisibility and torpidity, and the halogens by their variegated appearance and acridity, the non-metallic pre-halogen elements exhibit the following characteristics: (i) being sandwiched between the strongly electronegative halogen nonmetals and the 'weakly (non)metallic' metalloids, their physical and chemical character is overall 'moderately nonmetallic'; (ii) the elemental substances have a semi-metallic [graphitic carbon, black phosphorus (the most stable form under ambient conditions, now easily prepared by Tiouitchi et al, 2019), selenium] or colored (sulfur) or colorless (hydrogen, nitrogen, and oxygen) appearance and possess a brittle comportment if in solid phase (including N under high pressure: Cheng et al, 2020;Ji et al, 2020;Laniel et al, 2020); (iii) they show an overall tendency to form covalent compounds featuring localized and catenated bonds as chains, rings, and layers; (iv) in light of their relatively small atomic radii and sufficiently low ionization energy values, a capacity to form interstitial and refractory compounds (West, 1931;Goldschmidt, 1967;Glasson and Jayaweera, 1968;Wulfsberg, 2000); (v) prominent geological, biochemical (beneficial and toxic), organocatalytic, and energetic aspects (Akerfeldt and Fagerlind, 1967;Hutzinger, 1980;Dalko and Moisan, 2004;Nancharaiah and Lens, 2015;Vernon, 2020a).…”

Section: Periodically Unexpected Facts Finally Accommodatedmentioning

confidence: 99%

Understanding Periodic and Non-periodic Chemistry in Periodic Tables

et al. 2021

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The chemical elements are the “conserved principles” or “kernels” of chemistry that are retained when substances are altered. Comprehensive overviews of the chemistry of the elements and their compounds are needed in chemical science. To this end, a graphical display of the chemical properties of the elements, in the form of a Periodic Table, is the helpful tool. Such tables have been designed with the aim of either classifying real chemical substances or emphasizing formal and aesthetic concepts. Simplified, artistic, or economic tables are relevant to educational and cultural fields, while practicing chemists profit more from “chemical tables of chemical elements.” Such tables should incorporate four aspects: (i) typical valence electron configurations of bonded atoms in chemical compounds (instead of the common but chemically atypical ground states of free atoms in physical vacuum); (ii) at least three basic chemical properties (valence number, size, and energy of the valence shells), their joint variation across the elements showing principal and secondary periodicity; (iii) elements in which the (sp)8, (d)10, and (f)14valence shells become closed and inert under ambient chemical conditions, thereby determining the “fix-points” of chemical periodicity; (iv)peculiar elements at the top and at the bottom of the Periodic Table. While it is essential that Periodic Tables display important trends in element chemistry we need to keep our eyes open for unexpected chemical behavior in ambient, near ambient, or unusual conditions. The combination of experimental data and theoretical insight supports a more nuanced understanding of complex periodic trends and non-periodic phenomena.

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Selenophosphorus Compounds as Powerful Cholinesterase Inhibitors

Cited by 16 publications

References 0 publications

Imines, Cyclic

Imines, Cyclic

Chemical, Physical, and Toxicological Properties of V-Agents

Understanding Periodic and Non-periodic Chemistry in Periodic Tables

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