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(E)-2-Benzylidenecyclohexanones: Part XIX. Reaction Of (E)-2-(4′-X-benzylidene)-1-Tetralones with Cellular Thiols. Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs [1]
Version 1
: Received: 30 April 2024 / Approved: 30 April 2024 / Online: 2 May 2024 (07:59:52 CEST)
How to cite:
Kenari, F.; Pintér, Z.; Molnár, S.; Borges, I. D.; Camargo, A. J.; Napolitano, H. B.; Perjési, P. (E)-2-Benzylidenecyclohexanones: Part XIX. Reaction Of (E)-2-(4′-X-benzylidene)-1-Tetralones with Cellular Thiols. Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs [1]. Preprints2024, 2024050036. https://doi.org/10.20944/preprints202405.0036.v1
Kenari, F.; Pintér, Z.; Molnár, S.; Borges, I. D.; Camargo, A. J.; Napolitano, H. B.; Perjési, P. (E)-2-Benzylidenecyclohexanones: Part XIX. Reaction Of (E)-2-(4′-X-benzylidene)-1-Tetralones with Cellular Thiols. Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs [1]. Preprints 2024, 2024050036. https://doi.org/10.20944/preprints202405.0036.v1
Kenari, F.; Pintér, Z.; Molnár, S.; Borges, I. D.; Camargo, A. J.; Napolitano, H. B.; Perjési, P. (E)-2-Benzylidenecyclohexanones: Part XIX. Reaction Of (E)-2-(4′-X-benzylidene)-1-Tetralones with Cellular Thiols. Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs [1]. Preprints2024, 2024050036. https://doi.org/10.20944/preprints202405.0036.v1
APA Style
Kenari, F., Pintér, Z., Molnár, S., Borges, I. D., Camargo, A. J., Napolitano, H. B., & Perjési, P. (2024). (E)-2-Benzylidenecyclohexanones: Part XIX. Reaction Of (E)-2-(4′-X-benzylidene)-1-Tetralones with Cellular Thiols. Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs [1]. Preprints. https://doi.org/10.20944/preprints202405.0036.v1
Chicago/Turabian Style
Kenari, F., Hamilton B Napolitano and Pál Perjési. 2024 "(E)-2-Benzylidenecyclohexanones: Part XIX. Reaction Of (E)-2-(4′-X-benzylidene)-1-Tetralones with Cellular Thiols. Comparison of Thiol Reactivities of Open-Chain Chalcones and Their Six- and Seven-Membered Cyclic Analogs [1]" Preprints. https://doi.org/10.20944/preprints202405.0036.v1
Abstract
Non-enzyme-catalyzed thiol addition onto the α,β-unsaturated carbonyl system is associated with several biological effects. Kinetics and diastereoselectivity of non-enzyme catalyzed nucleophilic addition of GSH and NAC to the six-membered cyclic chalcone analogs 2a and 2b were investigated at different pH values (pH 3.2, 7.4 and 8.0). The selected compounds displayed in vitro cancer cell cytotoxicity (IC50) of different orders of magnitude. The chalcones intrinsically reacted with both thiols under all incubation conditions. The initial rates and compositions of the final mixtures depended both on the substitution and the pH. The stereochemical outcome of the reactions was evaluated by HPLC-UV method. The structure of the formed thiol-conjugates and the retro-Michael products (Z)-2a and (Z)-2b were confirmed by HPLC-MS. The frontier molecular orbitals and the Fukui function were carried out to investigate their effects on the six-membered cyclic analogs. Data were compared with those obtained with the open-chain (1) and the seven-membered (3) analogs. The observed reactivities do not directly relate to the difference in in vitro cancer cell cytotoxicity of the compounds.
Keywords
chalcone; glutathione; cysteine; thiols; Michael addition; diastereoselective addition
Subject
Chemistry and Materials Science, Medicinal Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
