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1 Supplementary Information J. Braz. Chem. Soc., Vol. 27, No. 9, S1-S16, Printed in Brazil Sociedade Brasileira de Química $ Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles to Design New Acetylcholinesterase Inhibitors: Fast and Easy Generation of 4-Methylcoumarins/1,2,3-triazoles Conjugates via Click Chemistry Fernando C. Torres, a,b Guilherme A. Gonçalves, a Kenia L. Vanzolini, c Aloir A. Merlo, d Bruna Gauer, a Maribete Holzschuh, a Saulo Andrade, a Maristela Piedade, a Solange C. Garcia, a Ivone Carvalho, e Gilsane L. von Poser, a Daniel F. Kawano,*,f,g Vera L. Eifler-Lima*,a and Quezia B. Cass c a Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, Porto Alegre-RS, Brazil b Faculdade de Farmácia, Centro Universitário Ritter dos Reis, Porto Alegre-RS, Brazil c Departamento de Química, Universidade Federal de São Carlos, São Carlos-SP, Brazil d Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre-RS, Brazil e Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto-SP, Brazil f Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, Campinas-SP, Brazil g Departamento de Química Orgânica, Instituto de Química, Universidade Estadual de Campinas, Campinas-SP, Brazil Figure S1. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 3 (LaSOM 77). * veraeifler@ufrgs.br; daniel.kawano@fcf.unicamp.br

2 S2 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S2. 13 C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 3 (LaSOM 77). Figure S3. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 5 (LaSOM 183).

3 Vol. 27, No. 9, 2016 Torres et al. S3 Figure S4. 13 C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 5 (LaSOM 183). Figure S5. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7a (LaSOM 180).

4 S4 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S6. 13 C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 7a (LaSOM 180). Figure S7. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 7b (LaSOM 226).

5 Vol. 27, No. 9, 2016 Torres et al. S5 Figure S8. 13 C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 7b (LaSOM 226). Figure S9. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 7c (LaSOM 224).

6 S6 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 7c (LaSOM 224). Figure S11. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7d (LaSOM 190).

7 Vol. 27, No. 9, 2016 Torres et al. S7 Figure S C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 7d (LaSOM 190). Figure S13. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7e (LaSOM 221).

8 S8 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 7e (LaSOM 221). Figure S15. 1 H NMR spectrum (400 MHz, CDCl 3 ) of compound 7f (LaSOM 198).

9 Vol. 27, No. 9, 2016 Torres et al. S9 Figure S C NMR spectrum (100 MHz, CDCl 3 ) of compound 7f (LaSOM 198). Figure S17. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 7g (LaSOM 206).

10 S10 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 7g (LaSOM 206). Figure S19. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7h (LaSOM 199).

11 Vol. 27, No. 9, 2016 Torres et al. S11 Figure S C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 7h (LaSOM 199). Figure S21. 1 H NMR spectrum (400 MHz, CDCl 3 ) of compound 7i (LaSOM 218).

12 S12 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S C NMR spectrum (100 MHz, CDCl 3 ) of compound 7i (LaSOM 218). Figure S23. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7j (LaSOM 197).

13 Vol. 27, No. 9, 2016 Torres et al. S13 Figure S C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 7j (LaSOM 197). Figure S25. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7k (LaSOM 209).

14 S14 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S26. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 7l (LaSOM 196). Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 7l (LaSOM 196).

15 Vol. 27, No. 9, 2016 Torres et al. S15 Figure S28. 1 H NMR spectrum (300 MHz, DMSO-d 6 ) of compound 7m (LaSOM 191). Figure S C NMR spectrum (75 MHz, DMSO-d 6 ) of compound 7m (LaSOM 191).

16 S16 Combining the Pharmacophore Features of Coumarins and 1,4-Substituted 1,2,3-Triazoles J. Braz. Chem. Soc. Figure S30. 1 H NMR spectrum (400 MHz, DMSO-d 6 ) of compound 7n (LaSOM 213). Figure S C NMR spectrum (100 MHz, DMSO-d 6 ) of compound 7n (LaSOM 213).

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