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Volumn , Issue 1, 2008, Pages 0061-0064

Syntheses of the proposed structures of poison-frog alkaloids 179 and 207E and their inhibitory effects on neuronal nicotinic acetylcholine receptors

Author keywords

Dehydro 5,8 disubstituted indolizidines; Inhibitory effects on neuronal nicotinic acetylcholine receptors; Poison frog alkaloids 179 and 207E

Indexed keywords

ALKALOID; INDOLIZIDINE ALKALOID; NATURAL PRODUCT; NICOTINIC RECEPTOR; POISON;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; FROG; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; INHIBITION KINETICS; NONHUMAN; SYNTHESIS;

EID: 38549131753 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000831 Document Type: Article

Times cited : (11)

References (19)

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17
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- The spectral and analytical data of synthetic 1 are as follows: IR (neat, 3025, 2957, 2871, 2781, 1456, 1377, 1326, 1287, 1179, 913, 798, 715 cm-1. 1H NMR (500 MHz, CDCl3, δ, 0.93 (3 H, t, J, 7.5 Hz, 0.94 (3 H, d, J, 6.8 Hz, 1.25-1.34 (1 H, m, 1.35-1.41 (1 H, m, 1.42-1.52(2 H, m, 1.61-1.67 (1 H, m, 1.68-1.75 (1 H, m, 1.76-1.83 (1 H, m, 1.84 (1 H, td, J, 9.1, 6.9 Hz, 1.99-2.07 (2 H, m, 2.08-2.14 (1 H, m, 2.64 (1 H, dtd, J, 11.0, 3.6, 1.9 Hz, 3.35 (1 H, td, J, 8.4, 1.9 Hz, 5.50 (1 H, dt, J, 10.2, 1.9 Hz, 5.57 (1 H, dt, J, 10.2, 1.9 Hz, 13C NMR (75 MHz, CDCl3, δ, 14.39 (q, 18.14 (q, 18.64 (t, 20.77 (t, 29.38 (t, 36.04 (t, 37.61 (d, 52.79 (t, 63.00 (d, 67.83 (d, 128.55 (d, 131.53 (d, HRMS: m/z calcd for C12H21N: 179.1674; found: 179.1686, α]D26 +129.3 c 2.74, CHCl
- 3).

18
- 38549103416
- The spectral and analytical data of synthetic 2 are as follows: IR (neat, 3030, 2957, 2929, 2871, 2781, 1458, 1378, 1329, 1260, 1177, 1105, 929, 803, 713 cm-1. 1H NMR (500 MHz, CDCl3, δ, 0.89 (3 H, t, J, 6.8 Hz, 0.91 (3 H, t, J, 7.3 Hz, 1.12-1.21 (1 H, m, 1.23-1.34 (2 H, m, 1.35-1.40 (2 H, m, 1.43-1.53 (3 H, m, 1.59-1.68 (1 H, m, 1.69-1.74 (1 H, m, 1.76-1.82 (1 H, m, 1.93 (1 H, td, J, 9.4, 6.8 Hz, 1.99-2.06 (3 H, m, 2.63 (1 H, dtd, J, 11.0, 3.4, 1.7 Hz, 3.34 (1 H, td, J, 8.5, 2.1 Hz, 5.60 (1 H, dt, J, 9.8, 1.7 Hz, 5.63 (1 H, dt, J, 9.8, 1.7 Hz, 13C NMR (75 MHz, CDCl 3, δ, 14.43 (2 x q, 18.64 (t, 19.67 (t, 20.92 (t, 29.69 (t, 34.91 (t, 36.11 (t, 42.54 (d, 52.76 (t, 62.97 (d, 66.13 (d, 129.01 (d, 129.44 d, HRMS: m/z calcd for C14H75N 207.1986; found: 207.1973, α]D26 +10
- R = 8.41 min. MS (EI): m/z (%) = 208 (12), 207 (4), 206 (8), 164 (100), 162 (13), 136 (13), 134 (13), 132 (8), 120 (52), 106 (8), 93 (22), 92 (11), 91 (10), 79 (13), 77 (16), 70 (16), 67 (24), 65 (14). MS (EI) of natural product from Dendrobates granuliferous: m/z (%) = 207 (2), 206 (4), 17 (10), 164 (100), 162 (78), 134 (18), 120 (28), 91 (12), 79 (14), 77 (20), 65 (11).

19
- 4844221318
- Tsuneki, H.; You, Y.; Toyooka, N.; Kagawa, S.; Kobayashi, S.; Sasaoka, T.; Nemoto, H.; Kimura, I.; Dani, J. A. Mol. Pharmacol. 2004, 66, 1061.
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- Tsuneki, H.¹ You, Y.² Toyooka, N.³ Kagawa, S.⁴ Kobayashi, S.⁵ Sasaoka, T.⁶ Nemoto, H.⁷ Kimura, I.⁸ Dani, J.A.⁹

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