Late-Stage Oxygenation towards the Preparation of Metabolites of Agrochemical Active Ingredients †
1
Centro de Química Estrutural, Institute of Molecular Sciences, Universidade de Lisboa, 1049-001 Lisbon, Portugal
2
Department of Chemistry and Biochemistry, Faculdade de Ciências, Universidade de Lisboa, 1049-001 Lisbon, Portugal
3
ASCENZA Agro, S.A., Screening and Synthesis Laboratory, 2910-440 Setúbal, Portugal
*
Author to whom correspondence should be addressed.
†
Presented at the 8th International Electronic Conference on Medicinal Chemistry, 1–30 November 2022; Available online: https://ecmc2022.sciforum.net/ .
Med. Sci. Forum 2022, 14(1), 11; https://doi.org/10.3390/ECMC2022-13261
Published: 1 November 2022
(This article belongs to the Proceedings of The 8th International Electronic Conference on Medicinal Chemistry)
Abstract
:The development of plant protection products requires the safety profile analysis of active ingredients (AIs). This includes the toxicity determination of AI metabolites. A very common phase-one metabolism reaction is C-oxygenation catalyzed by cytochrome P450 enzymes. Thus, the synthesis of oxygenated AI metabolites is of great importance to agrochemical producing companies, namely ASCENZA Agro, for safety evaluation purposes. Herein, we describe the progress towards the synthesis of hydroxylated aromatic metabolites of several AIs using methods described by Tobias Ritter and co-workers. These methods allow the late-stage oxygenation of the aromatic and benzylic positions by generating mesylate derivatives with bis(methanesulfonyl) peroxide as an oxidant, followed by conversion to the corresponding phenols.
Supplementary Materials
The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/ECMC2022-13261/s1. Conference poster.
Funding
Financial support from Fundação para a Ciência e a Tecnologia (FCT, UIDB/00100/2020, UIDP/00100/2020, LA/P/0056/2020 and 2020/02383/CEECIND).
Institutional Review Board Statement
Not applicable.
Informed Consent Statement
Not applicable.
Data Availability Statement
Not applicable.
Conflicts of Interest
The authors declare no conflict of interest.
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MDPI and ACS Style
Clemente, D.B.; Monteiro, C.M.; Coelho, J.A.S. Late-Stage Oxygenation towards the Preparation of Metabolites of Agrochemical Active Ingredients. Med. Sci. Forum 2022, 14, 11. https://doi.org/10.3390/ECMC2022-13261
AMA Style
Clemente DB, Monteiro CM, Coelho JAS. Late-Stage Oxygenation towards the Preparation of Metabolites of Agrochemical Active Ingredients. Medical Sciences Forum. 2022; 14(1):11. https://doi.org/10.3390/ECMC2022-13261
Chicago/Turabian StyleClemente, Duarte B., Carlos M. Monteiro, and Jaime A. S. Coelho. 2022. "Late-Stage Oxygenation towards the Preparation of Metabolites of Agrochemical Active Ingredients" Medical Sciences Forum 14, no. 1: 11. https://doi.org/10.3390/ECMC2022-13261
