New Preparations of 1,2,4,5,7,8-Hexoxonanes

SUPPORTING INFORMATION

Cyclic peroxides as promising anticancer agents: in vitro cytotoxicity study of synthetic ozonides and tetraoxanes on human prostate cancer cell lines

Ivan A. Yaremenko,1,2 Mikhail A. Syroeshkin,1 Dmitri O. Levitsky,2,3 Fabrice Fleury,3 and Alexander O. Terent’ev. 1,2

Table of contents 1Fabrice Fleury

[email protected]

Alexander O. Terent’ev [email protected]

Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences Leninsky Prospect 47, Moscow, 119991,

Russian Federation

2 All-Russian Research Institute of Phytopathology, Bol’shie Vyazemy, Moscow region, 143050, Russian

Federation

3 UFIP CNRS UMR 6286, Mechanism and regulation of DNA repair team Université de Nantes, 2 rue de la

Houssinière, 44322, Nantes, France S1 NMR spectra of ozonides 1H NMR of 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S4 2-yl)ethanone, 2a 13C NMR of 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S5 2-yl)ethanone, 2a 1H NMR of 1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S6 2-yl)ethanone, 3a 13C NMR of 1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct- S7 2-yl)ethanone, 3a 1H NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S8 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b 13C NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S9 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b 1H NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S10 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b 13C NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8- S11 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b 1H NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S12 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с 13C NMR of 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S13 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с 1H NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S14 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c 13C NMR of 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8- S15 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c 1H NMR of 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S16 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d 13C NMR of 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S17 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d 1H NMR of 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S18 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d 13C NMR of 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8- S19 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d 1H NMR of 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S20 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e 13C NMR of 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S21 trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e 1H NMR of 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S22

S2 trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e 13C NMR of 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8- S23 trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e NMR spectra of tetraoxanes 1H NMR of 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, S24 5a 13C NMR of 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6- S25 tetraoxabicyclo[2.2.1]heptane, 5a 1H NMR of 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b S26 13C NMR of 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b S27

S3 NMR spectra of ozonides 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2a

S4 1-((1R,2R,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2a

1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3a S5 1-((1R,2S,5S)-2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3a

S6 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b

S7 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2b

S8 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b S9 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-nitrobenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3b

S10 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с S11 1-((1R,2R,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2с

S12 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c S13 1-((1R,2S,5S)-1,5-Dimethyl-2-(4-methylbenzyl)-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3c

S14 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d S15 1-((1R,2R,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2d

S16 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d

S17 1-((1R,2S,5S)-2-(4-Chlorobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 3d

S18 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e

S19 1-((1R,2R,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2-yl)ethanone, 2e

S20 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e

S21 1-((1R,2S,5S)-2-(4-bromobenzyl)-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]oct-2- yl)ethanone, 3e

S22 S23 NMR spectra of 1,2,4,5-tetraoxanes 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5a

S24 7-(1-Adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5a

S25 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b

S26 1-(1-Adamantyl)-4-methyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane, 5b