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Experimental details for compounds 1a-f, 2a-f, 3a-f and 4a-f. General methodsCommercially available reagents and solvents were used as received. Alkynes I, 12 II, 13 III 23 and IV 22 were synthesized as reported in the literature. Compound 3a has been reported elsewhere 5 and its spectroscopic characterization is consistent with the one described in this article. Flash column chromatography was performed on Kieselgel silica gel 60 (230-400 mesh). Melting points were determined on a Fisher-Johns apparatus and are uncorrected. IR spectra were recorded on a Bruker Alpha FT-IR/ATR spectrometer. NMR spectra were obtained with a JEOL ECA-500 (500 MHz) spectrometer. Chemical shifts (δ) are given in ppm downfield from Me 4 Si as an internal reference; coupling constants are given in Hertz.High-resolution mass spectra (HRMS) were recorded on a JEOL JMS-SX 102a and Agilent-MSD-TOF-1069A spectrometers 41. Typical procedure for the synthesis of 1,2,3-triazoles derived from methylaniline(1-Benzyl-1H-1,2,3-triazole-4-ylmethyl)-methyl-phenyl-amine (1a). To a 20 mL roundbottomed flask equipped with a magnetic stirrer, were charged 11 mg (0.053 mmol, 5 mol%) of Cu(OAc) 2 •H 2 O, 10 mg (0.053 mmol, 5 mol%) of 1,10-phenanthroline monohydrate, and 204 mg (1.03 mmol) of sodium L-ascorbate. After addition of 7 mL of a mixture EtOH-H 2 O (4:1 v/v), the resulting suspension was stirred for five minutes at room temperature. Subsequently, 150 mg (1.03 mmol) of (I), 81 mg (1.24 mmol) of sodium azide, and 0.14 mL (1.24 mmol) of benzyl chloride were added to the reaction mixture, which was stirred during 18 h at room temperature. 5 mL of H 2 O were added to the reaction mixture and the precipitate was filtered off, washed thoroughly with H 2 O, petroleum ether, and dried under vacuum. The crude product was purified by column chromatography

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Senna villosa (Miller) is a plant that grows in México. In traditional Mexican medicine, it is used topically to treat skin infections, pustules and eruptions and to heal wounds by scar formation. However, studies of its potential anti-inflammatory effects have not been performed. The aim of the present study was to determine the anti-inflammatory OPEN ACCESSMolecules 2014, 19 10262 effect of extracts from the leaves of Senna villosa and to perform a bioassay-guided chemical study of the extract with major activity in a model of ear edema induced by 12-O-tetradecanoylphorbol 13-acetate (TPA). The results reveal that the chloroform extract from Senna villosa leaves has anti-inflammatory and anti-proliferative properties. Nine fractions were obtained from the bioassay-guided chemical study, including a white precipitate from fractions 2 and 3. Although none of the nine fractions presented anti-inflammatory activity, the white precipitate exhibited pharmacological activity. It was chemically characterized using mass spectrometry and infrared and nuclear magnetic resonance spectroscopy, resulting in a mixture of three aliphatic esters, which were identified as the principal constituents: hexyl tetradecanoate (C 20 H 40 O 2 ), heptyl tetradecanoate (C 21 H 42 O 2 ) and octyl tetradecanoate (C 22 H 44 O 2 ). This research provides, for the first time, evidence of the anti-inflammatory and anti-proliferative properties of compounds isolated from Senna villosa.