Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

Rossetti, Arianna; Sacchetti, Alessandro; Bonfanti, Marta; Roda, Gabriella; Rainoldi, Giulia; Silvani, Alessandra

doi:10.1016/j.tet.2017.06.022

Cited by 11 publications

(2 citation statements)

References 47 publications

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“…Following from this, it is likely that the 441 degradation product results from the hydrogenation of the alkene in 3E‐ZIPR to form 3‐ethyl‐ziprasidone (3A‐ZIPR). This is supported by literature reports on the reduction of 3‐alkylidene oxindoles to 3‐alkyl oxindoles in the presence of Saccharomyces cerevisiae 43 and the reduction of caffeic acid to dihydrocaffeic acid by C. perfringens 44 . C. perfringens was also the dominant microorganism present in the inoculated, unpreserved blood specimens in the quantitative blood experiments 27 .…”

Section: Resultssupporting

confidence: 80%

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In vitro degradation of ziprasidone in human whole blood

Castle

Butzbach

Walker

et al. 2022

Drug Testing and Analysis

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A systematic study was performed into the degradation of ziprasidone in simulated postmortem blood. Fifteen potential degradation products not previously reported in the literature were observed. Four resulted from degradation in human blood, whereas the remaining products resulted from reaction with solvents: four from alkaline degradation, four from reaction with acetaldehyde, and three from reaction with acetone.To identify possible degradation products, a liquid chromatograph-diode array detector (LC-DAD) and liquid chromatograph quadrupole-time-of-flight mass spectrometer (LC-QTOF-MS) operating in auto-MS/MS mode were used. It was indicated from redshifted UV-Vis spectra, accurate mass data, mass fragmentation data, and a deuteration experiment that the site of ziprasidone degradation, in the in vitro blood experiments, was the methylene carbon of the oxindole moiety. The major in vitro blood degradation products were proposed to be E/Z isomers of 3-ethylidene-ziprasidone.Further, another in vitro degradation product in microbially inoculated blood specimens was proposed to be 3-ethyl-ziprasidone. 3-Ethylidene-ziprasidone was hypothesized to form from the reaction of ziprasidone with acetaldehyde derived from the ethanol used to spike ziprasidone into the in vitro blood experiments. Data from two postmortem investigations were available for retrospective reanalysis. Attempts were made to detect degradation products of ziprasidone, but none were found.

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Section: Resultssupporting

confidence: 80%

“…alkyl oxindoles in the presence of Saccharomyces cerevisiae43 and the reduction of caffeic acid to dihydrocaffeic acid by C. perfringens 44. C. perfringens was also the dominant microorganism present in the inoculated, unpreserved blood specimens in the quantitative blood experiments 27.…”

mentioning

confidence: 99%

In vitro degradation of ziprasidone in human whole blood

Castle

Butzbach

Walker

et al. 2022

Drug Testing and Analysis

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Part II: Diastereoselective Reactions Involving β‐Mono‐ and β,β′‐Disubstituted Alkylidene Oxindoles: Pondering Alkene Geometry

Ganesh¹,

Rao²

2017

Asian J Org Chem

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Part II encompasses synthetic efforts towards the construction of acyclic and cyclic structures that contain carbon and heteroatoms by employing diastereoselective reactions of β,β′‐disubstituted alkylidene oxindole as the primary substrate. In addition to the construction of acyclic structures, carbocyclic and heterocyclic rings that contain three‐, five‐, six‐, and seven‐membered spirocycles or fused‐rings are also described. A few examples of the arylative cyclization of dienes have also been presented.

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