Synthesis and in vitro kinetic evaluation of N-thiazolylacetamido monoquaternary pyridinium oximes as reactivators of sarin, O-ethylsarin and VX inhibited human acetylcholinesterase (hAChE)

Valiveti, Aditya Kapil; Bhalerao, Uma M.; Acharya, Jyotiranjan; Karade, Hitendra N.; Acharya, Badri Narayan; Raviraju, G.; Halve, Anand K.; Kaushik, M. P.

doi:10.1016/j.bmc.2015.05.027

Cited by 13 publications

(3 citation statements)

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“…To reduce the overall cost, we chose to use (R)-1phenyl-1,2-ethanediol (12) to replace the expensive (R)styrene oxide (7). The terminal hydroxyl hydrogen in compound 12 was replaced by either p-toluenesufonyl or mesylsulfonyl group under the action of triethylamine and dibutyl tin oxide to produce (R)-1-phenyl-2tosylethanol (13) or (R)-2-(methylsulfonyl)-1phenylethanol, respectively [14][15][16][17][18]. We found that, during the production of compound 6, (R)-1-phenyl-2tosylethanol reacted faster and more efficient than (R)-2-(methylsulfonyl)-1-phenylethanol, which was possibly because of benzene ring conjugation effect.…”

Section: Resultsmentioning

confidence: 99%

Study on a New Method for Synthesis of Mirabegron

Mao

et al. 2017

Journal of Heterocyclic Chem

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Mirabegron is a muscle relaxing drug for the treatment of overactive bladder. The existing synthetic methods for mirabegron produced intermediate product 4‐(2‐(phenethylamino)ethyl)aniline, which complicated the final product purification process. In this study, we designed a new synthetic route for mirabegron with low cost starting materials and a production of mirabegron at a 99.6% purity and a 61% overall yield. Particularly, this new synthetic route did not produce side product 4‐(2‐(phenethylamino)ethyl)aniline, which significantly simplified the product purification process.

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Section: Resultsmentioning

confidence: 99%

Study on a New Method for Synthesis of Mirabegron

Mao

et al. 2017

Journal of Heterocyclic Chem

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“…Better reactivation with the studied bis-pyridinium oximes bearing oxime function at 4 th position could be attributed to electronic and steric effects 29 . The higher reactivation efficacy of 3a and 3d for DFP inhibited AChE at the lower concentration 10 -4 M in comparison to 2-PAM and obidoxime showed that they can be promising candidates for in-vivo reactivation as well.…”

Section: Discussionmentioning

confidence: 99%

In-vitro Evaluation of Bis-pyridinium Oximes Connected by Xylene Linkers as Reactivators of DFP-inhibited Electric EEL Acetylcholinesterase

et al. 2016

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Bis-pyridinium oximes connected by xylene linkers were synthesised and their in-vitro reactivation efficacy was evaluated for DFP inhibited AChE. The reactivation efficacy data were compared with those of 2-PAM and obidoxime. However, it was observed that none of these oximes were able to surpass the reactivation efficacy of 2-PAM and obidoxime in reactivating DFP inhibited AChE. 2-PAM and obidoxime respectively exhibited 52 per cent and 43 per cent reactivation of DFP inhibited AChE, where as the synthesised oximes 3a, 3d, and 3f showed 37 per cent, 30 per cent, and 31 per cent reactivation, respectively within 10 min at 10 -3 M.Keywords: Bis-pyridinium oximes, Reactivators, 2-PAM, DFP, organophosphorus pesticides, nerve agents, acetylcholinesterase, obidoxime Figure 1. organophosphorus pesticides and nerve agents.

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“…This nitrile-containing heterocycle is generally produced via the bromo precursor in a step-inefficient manner. The 2-aminothiazole is synthesized from readily available starting materials and then converted to 2-bromothiazole via a Sandmeyer reaction . Substitution of bromine by a nitrile group is then achieved by a copper-catalyzed coupling with ferricyanide, or via the aldehyde through lithium–halogen exchange …”

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confidence: 99%

Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2-Cyanothiazole Derivatives

et al. 2023

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The expeditious synthesis of an API building block, 2-cyanothiazole, from cyanogen gas and a readily available dithiane is reported. A previously undisclosed partially saturated intermediate is formed, which can be further functionalized and isolated by the acylation of the hydroxy group. Dehydration using trimethylsilyl chloride furnished 2-cyanothiazole, which could be further converted to the corresponding amidine. The sequence provided a 55% yield over 4 steps. We envision that this work will spark further interest in cyanogen gas as a reactive and costeffective synthetic reagent.

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Synthesis and in vitro kinetic evaluation of N-thiazolylacetamido monoquaternary pyridinium oximes as reactivators of sarin, O-ethylsarin and VX inhibited human acetylcholinesterase (hAChE)

Cited by 13 publications

References 51 publications

Study on a New Method for Synthesis of Mirabegron

Study on a New Method for Synthesis of Mirabegron

In-vitro Evaluation of Bis-pyridinium Oximes Connected by Xylene Linkers as Reactivators of DFP-inhibited Electric EEL Acetylcholinesterase

Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2-Cyanothiazole Derivatives

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