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Pure Appl. Chem., 2012, Vol. 84, No. 9, pp. 1867-1875

http://dx.doi.org/10.1351/PAC-CON-11-10-21

Published online 2012-04-29

First total synthesis of the (±)-2-methoxy-6-heptadecynoic acid and related 2-methoxylated analogs as effective inhibitors of the Leishmania topoisomerase IB enzyme

Néstor M. Carballeira1*, Michelle Cartagena1, Fengyu Li1, Zhongfang Chen1, Christopher F. Prada2, Estefania Calvo-Alvarez2, Rosa M. Reguera2 and Rafael Balaña-Fouce2

1 Department of Chemistry, University of Puerto Rico, Rio Piedras campus, P.O. Box 23346, San Juan, Puerto Rico
2 Department of Biomedical Sciences, University of León, Campus de Vegazana s/n, 24071 León, Spain

References

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  • 10. Spectral data for the (±)-2-methoxy-6-heptadecynoic acid (2). IR (neat) νmax: 3365, 2926, 2855, 1734, 1457, 1380, 1119 cm–1; 1H NMR (CDCl3, 500 MHz) δ (ppm): 3.83 (1H, t, J = 4.6 Hz), 3.44 (3H, s, –OCH3), 2.20 (2H, t, J = 7.0 Hz), 2.12 (2H, t, J = 6.9 Hz), 1.62 (2H, q, J = 7.2 Hz), 1.25 (18H, brs, –CH2–), 0.87 (3H, t, J = 6.9 Hz, –CH3); 13C NMR (CDCl3, 125 MHz) δ (ppm): 176.97 (C-1), 81.07 (C-7), 79.72 (C-2), 79.02 (C-6), 58.24 (C-2'), 31.88 (C-15), 31.36 (C-13), 29.57 (C-12), 29.52 (C-14), 29.30 (C-9), 29.14 (C-11), 28.88 (C-3), 24.44 (C-16), 22.66 (C-4), 18.71 (C-5), 18.45 (C-8), 14.09 (C-17). HRMS calcd for C18H32O3 [M + H]+ 297.2424, found 297.2423.
  • 11. Spectral data for the (±)-2-methoxy-6Z-heptadecenoic acid (1). IR (neat) νmax: 3330, 3005, 2928, 2856, 1720, 1650, 1458, 1380, 969, 778 cm–1; 1H NMR (CDCl3, 500 MHz) δ (ppm): 5.35 (2H, m), 3.78 (1H, t, J = 6.7 Hz), 3.42 (3H, s, –OCH3), 2.01 (4H, m), 1.76 (2H, m), 1.23 (18H, brs, –CH2–), 0.85 (3H, t, J = 7.0 Hz, –CH3); 13C-NMR (CDCl3, 125 MHz) δ (ppm): 176.87 (C-1), 131.26 (C-7), 129.04 (C-6), 80.46 (C-2), 58.28 (C-2'), 31.88 (C-15), 31.81 (C-3, C-9), 29.67 (C‑10), 29.61 (C-11), 29.53 (C-12), 29.41 (C-13), 29.31 (C-14), 27.23 (C-8), 26.71 (C-5), 24.83 (C-4), 22.67 (C-16), 14.13 (C-17). HRMS Calcd for C18H35O3 [M + H]+ 299.2581, found 299.2583.
  • 12. Spectral data for the (±)-2-methoxyheptadecanoic acid (3). IR (neat) νmax: 3420, 2922, 2852, 1716, 1457, 1381, 1090 cm–1; 1H-NMR (CDCl3, 500 MHz) δ (ppm): 3.79 (1H, t, J = 5.0 Hz), 3.46 (3H, s, –OCH3), 1.52 (2H, m), 1.28 (26H, brs, –CH2–), 0.87 (3H, t, J = 6.7 Hz, –CH3); 13C‑NMR (CDCl3, 125 MHz) δ (ppm): 175.89 (C-1), 80.27 (C-2), 58.34 (C-2'), 32.22 (C-15), 31.93 (C-3), 29.70 (C-12, C-13), 29.67 (C-10, C-11), 29.63 (C-9), 29.55 (C-8), 29.42 (C-7), 29.37 (C-6), 29.32 (C-5), 29.08 (C-14), 24.82 (C-4), 22.70 (C-16), 14.13 (C-17).
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