Eugenol derived immunomodulatory molecules against visceral leishmaniasis

Synthesis, Antimicrobial Activity and in silico Studies on Eugenol Eters

“…C 18 H 26 O 3 (M = 290.40); yield 86%; MS (EI): m/z (%) 290 (M + ), 165 (16.52), 164 (100), 149 (10.31), 133 (5.41), 132 (4.60), 131 (5.81), 103 (4.60), 91 (5.21), 57 (10.21), 55 (7.71); RI (HP5-MS): 2141; 1 H NMR (500.13 MHz, CDCl 3 ): δ 6.96 (1H, d, J = 8.3 Hz, H-6), 6.76-6.83 (2H, m, H-3 and H-5), 5.94-6.03 (1H, m, H-9), 5.09-5.18 (2H, m, H-10), 3.83 (3H, s, C-7), 3.40 (2H, d, J = 6.2 Hz, H-8), 2.59 (2H, t, J = 7.3 Hz, H-12), 1.79 (2H, quin, J = 7.3 Hz, H-13), 1.28-1.49 (8H, bm, H-14-H-17), 0.88-0.97 (3H, m, H-18); 13 C NMR (125.76 MHz, CDCl 3 ): δ 172.08 (C-11), 150.93 (C-2), 138.86 (C-1), 138.09 (C-4), 137.13 (C-9), 122.57 (C-6), 120.68 (C-5), 116.13 (C-10), 112.73 (C-3), 55.81 (C-7), 40.12 (C-8), 34.10 (C-12), 31.73 (C-16), 29.05 (C-15), 28.97 (C-14), 25.10 (C-13), 22.64 (C-17), 14.11 (C-18). Physical and spectroscopic data were in accordance with those reported 38. Eugenyl Nonanoate (3j)Chromatographic purification gave yellowish oil.C 19 H 28 O 3 (M = 304.42); yield 76%; MS (EI): m/z (%) 304 (M + ), 165 (11.31), 164 (100), 149 (9.01), 137 (1.90), 133 Lazarević et al: Synthesis, Antimicrobial Activity ...…”

“…40), 132 (4.60), 131 (3.10), 121 (1.50), 107 (1.30), 104 (2.00); RI (HP5-MS): 2246; 1 H NMR (500.13 MHz, CDCl 3 ): δ 6.96 (1H, d, J = 8.3 Hz, H-6), 6.70-6.84 (2H, m, H-3 and H-5), 5.92-6.04 (1H, m, H-9), 5.03-5.18 (2H, m, H-10), 3.83 (3H, s, C-7), 3.40 (2H, d, J = 6.2 Hz, H-8), 2.59 (2H, t, J = 7.3 Hz, H-12), 1.78 (2H, quin, J = 7.5 Hz, H-13), 1.29-1.49 (10H, bm, H-14-H-18), 0.83-1.06 (3H, m, H-19); 13 C NMR (125.76 MHz, CDCl 3 ): δ 172.08 (C-11), 150.93 (C-2), 138.86 (C-1), 138.09 (C-4), 137.13 (C-9), 122.57 (C-6), 120.68 (C-5), 116.13 (C-10), 112.73 (C-3), 55.81 (C-7), 40.11 (C-8), 34.10 (C-12), 31.84 (C-17), 29.27 (C-16), 29.19 (C-15), 29.10 (C-14), 25.09 (C-13), 22.68 (C-18), 14.13 (C-19). Physical and spectroscopic data were in accordance with those reported 38. Eugenyl Decanoate (3k)Chromatographic purification gave colorless oil.C 20 H 30 O 3 (M = 318.45); yield 85%; MS (EI): m/z (%) 318 (M + ), 166 (1.00), 165 (11.31), 164 (100), 149 (7.91), 147 (1.00), 137 (1.70), 133 (4.40), 105 (1.50), 103 (4.00); 85 (1.40); RI (HP5-MS): 2348; 1 H NMR (500.13 MHz, CDCl 3 ): δ 6.96 (1H, d, J = 7.6 Hz, H-6), 6.78-6.82 (2H, m, H-3 and H-5), 5.95-6.04 (1H, m, H-9), 5.10-5.17 (2H, m, H-10), 3.83 (3H, s, C-7), 3.40 (2H, d, J = 6.2 Hz, H-8), 2.59 (2H, t, J = 7.6 Hz, H-12), 1.79 (2H, quin, J = 7.6 Hz, H-13), 1.27-1.48 (12H, bm, H-14-H-19), 0.92 (3H, t, J = 6.9 Hz, H-20); 13 C NMR (125.76 MHz, CDCl 3 ): δ 172.08 (C-11), 150.93 (C-2), 138.86 (C-1), 138.09 (C-4), 137.13 (C-9), 122.57 (C-6), 120.68 (C-5), 116.13 (C-10), 112.73 (C-3), 55.81 (C-7), 40.12 (C-8), 34.10 (C-12), 31.91 (C-18), 29.5 (C-16), 29.32 (2 × CH 2 : C-15 and C-17), 29.10 (C-14), 25.10 (C-13), 22.71 (C-19), 14.14 (C-20).…”

“…Physical and spectroscopic data were in accordance with those reported. 37,38 Eugenyl Propanoate (3b)…”

“…Physical and spectroscopic data were in accordance with those reported. 11,38 . Physical and spectroscopic data were in accordance with those reported.…”

“…Several papers on isolation and/or synthesis and biological activity of eugenyl esters have reported wide range of activities: antioxidant, 9,11,13,34 anticancer, 35 larvicidal, 37 anti-leishmaniasis. 38 On the other hand, little data exists on antimicrobial activity, reporting only few compounds involved with respect to the total number synthesized. Antimicrobial assays evaluated antibacterial activity of eugenyl esters of acetic, 3-methylbutanoic, pentanoic and benzoic acids, [31][32][33] but no data related to antifungal activity of such derivatives was reported.…”