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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 216 Supplementary Information Design, synthesis, and biological evaluation of novel asiatic acid derivatives as potential anticancer agents Bruno M.F. Gonçalves, a,b Jorge A. R. Salvador, a,b* Diana S. M. Santos, a Silvia Marín, c,d and Marta Cascante c,d* a Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Coimbra, Portugal. Fax: ; Tel: ; salvador@ci.uc.pt. b Center for Neuroscience and Cell Biology, Coimbra, Portugal. c Department of Biochemistry and Molecular Biology, Faculty of Biology, University of Barcelona, Diagonal 643, 828 Barcelona, Spain; Tel ; martacascante@ub.edu d Institute of Biomedicine of University of Barcelona (IBUB) and Associated Unit to CSIC, Barcelona, Spain. 1
2 Table of Contents 1. NMR data for compound H-NMR spectrum for compound 7 recorded in CDCl C-NMR spectrum for compound 7 recorded in CDCl DEPT135 spectrum for compound 7 recorded in CDCl NMR data for compound H-NMR spectrum for compound 8 recorded in CDCl C-NMR spectrum for compound 8 recorded in CDCl DEPT135 spectrum for compound 8 recorded in CDCl NMR data for compound H-NMR spectrum for compound 9 recorded in CDCl C-NMR spectrum for compound 9 recorded in CDCl DEPT135 spectrum for compound 9 recorded in CDCl NMR data for compound H-NMR spectrum for compound 1 recorded in CDCl C-NMR spectrum for compound 1 recorded in CDCl DEPT135 spectrum for compound 1 recorded in CDCl NMR data for compound 11: H-NMR spectrum for compound 11 recorded in CDCl C-NMR spectrum for compound 11 recorded in CDCl DEPT135 spectrum for compound 11 recorded in CDCl NMR data for compound H-NMR spectrum for compound 12 recorded in CDCl C-NMR spectrum for compound 12 recorded in CDCl DEPT135 spectrum for compound 12 recorded in CDCl NMR data for compound H-NMR spectrum for compound 13 recorded in CDCl C-NMR spectrum for compound 13 recorded in CDCl DEPT135 spectrum for compound 13 recorded in CDCl NMR data for compound H-NMR spectrum for compound 14 recorded in CDCl
3 C-NMR spectrum for compound 14 recorded in CDCl DEPT135 spectrum for compound 14 recorded in CDCl NMR data for compound H-NMR spectrum for compound 15 recorded in CDCl C-NMR spectrum for compound 15 recorded in CDCl DEPT135 spectrum for compound 15 recorded in CDCl NMR data for compound H-NMR spectrum for compound 16 recorded in CDCl C-NMR spectrum for compound 16 recorded in CDCl DEPT135 spectrum for compound 16 recorded in CDCl NMR data for compound H-NMR spectrum for compound 17 recorded in CDCl C-NMR spectrum for compound 17 recorded in CDCl DEPT135 spectrum for compound 17 recorded in CDCl
4 1. NMR data for compound H-NMR spectrum for compound 7 recorded in CDCl 3 H N H E+8 6E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E
5 C-NMR spectrum for compound 7 recorded in CDCl 3 H N H E+7 5E+7 4E+7 4E+7 4E+7 3E+7 2E+7 2E+7 2E+7 1E+7 5E+6-5E
6 1.3 DEPT135 spectrum for compound 7 recorded in CDCl 3 H N H E+8 6E+8 5E+8 4E+8 3E E+8-4E+8-5E
7 2. NMR data for compound H-NMR spectrum for compound 8 recorded in CDCl 3 CH 3 N H E+8 6E+8 6E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E
8 C-NMR spectrum for compound 8 recorded in CDCl 3 CH 3 N H E+7 8E+7 7E+7 6E+7 5E+7 4E+7 3E+7 2E+7 1E+7-1E
9 2.3 DEPT135 spectrum for compound 8 recorded in CDCl 3 CH 3 N H E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E+7-5E E+8-4E
10 3. NMR data for compound H-NMR spectrum for compound 9 recorded in CDCl 3 Ac NH H 9E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E
11 C-NMR spectrum for compound 9 recorded in CDCl 3 Ac NH H E+7 4E+7 4E+7 3E+7 2E+7 2E+7 2E+7 1E+7 5E
12 3.3 DEPT135 spectrum for compound 9 recorded in CDCl 3 Ac NH H E+9 9E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E E+8-4E
13 4. NMR data for compound H-NMR spectrum for compound 1 recorded in CDCl 3 Ac N N E+9 1E+9 9E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E ppm
14 C-NMR spectrum for compound 1 recorded in CDCl 3 Ac N N E+8 3E+8 5E ppm
15 4.3 DEPT135 spectrum for compound 1 recorded in CDCl 3 Ac N N E+8 5E+8 4E+8 3E E ppm
16 5 NMR data for compound 11: H-NMR spectrum for compound 11 recorded in CDCl 3 Ac NHCH E+8 6E+8 6E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E
17 C-NMR spectrum for compound 11 recorded in CDCl 3 Ac NHCH E+7 8E+7 7E+7 6E+7 5E+7 4E+7 3E+7 2E+7 1E+7-1E
18 5.3 DEPT135 spectrum for compound 11 recorded in CDCl 3 Ac NHCH E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E E+8-4E+8-5E+8-6E+8-7E
19 6. NMR data for compound H-NMR spectrum for compound 12 recorded in CDCl 3 Ac NHCH 2 CH E+8 8E+8 7E+8 6E+8 6E+8 6E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E ppm
20 C-NMR spectrum for compound 12 recorded in CDCl 3 Ac NHCH 2 CH E+7 6E+7 4E+7 2E+7-2E ppm
21 6.3 DEPT135 spectrum for compound 12 recorded in CDCl 3 Ac NHCH 2 CH E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E E+8-4E+8-5E+8-6E+8-7E+8-8E ppm
22 7. NMR data for compound H-NMR spectrum for compound 13 recorded in CDCl 3 Ac NHCH 2 CH 2 CH E+8 7E+8 6E+8 6E+8 6E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E
23 C-NMR spectrum for compound 13 recorded in CDCl 3 Ac NHCH 2 CH 2 CH E ppm
24 7.3 DEPT135 spectrum for compound 13 recorded in CDCl 3 Ac NHCH 2 CH 2 CH E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E+7-5E E+8-4E+8-4E ppm
25 8. NMR data for compound H-NMR spectrum for compound 14 recorded in CDCl 3 Ac H N CH E+9 9E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E
26 C-NMR spectrum for compound 14 recorded in CDCl 3 Ac H N CH E+7 6E+7 4E+7 2E+7-2E
27 8.3 DEPT135 spectrum for compound 14 recorded in CDCl 3 Ac H N CH E+8 7E+8 6E+8 5E+8 4E+8 3E E+8-4E+8-5E
28 9. NMR data for compound H-NMR spectrum for compound 15 recorded in CDCl 3 Ac H N F E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E
29 C-NMR spectrum for compound 15 recorded in CDCl 3 Ac H N F E+7 8E+7 7E+7 6E+7 5E+7 4E+7 3E+7 2E+7 1E+7-1E+7-2E ppm
30 9.3 DEPT135 spectrum for compound 15 recorded in CDCl 3 Ac H N F E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E E+8-4E ppm
31 1. NMR data for compound H-NMR spectrum for compound 16 recorded in CDCl 3 Ac NHCH 2 CCH E+8 6E+8 6E+8 5E+8 4E+8 4E+8 4E+8 3E+8 5E E
32 C-NMR spectrum for compound 16 recorded in CDCl 3 Ac NHCH 2 CCH E+7 8E+7 7E+7 6E+7 5E+7 4E+7 3E+7 2E+7 1E+7-1E+7-2E
33 1.3 DEPT135 spectrum for compound 16 recorded in CDCl 3 Ac NHCH 2 CCH E+8 5E+8 4E+8 3E E+8-4E+8-5E
34 11. NMR data for compound H-NMR spectrum for compound 17 recorded in CDCl 3 Ac NHCH(CH 3 )CCH E+8 4E+8 4E+8 3E+8 5E
35 C-NMR spectrum for compound 17 recorded in CDCl 3 Ac NHCH(CH 3 )CCH E+7 8E+7 7E+7 6E+7 5E+7 4E+7 3E+7 2E+7 1E+7-1E
36 11.3 DEPT135 spectrum for compound 17 recorded in CDCl 3 Ac NHCH(CH 3 )CCH E+8 8E+8 7E+8 6E+8 5E+8 4E+8 3E E+8-4E+8-5E+8-6E
37 37
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