Smenamides A and B

Smenamides A and B


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3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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Mar. Drugs 2013, 11(11), 4451-4463; doi:10.3390/md11114451 - See more at: http://www.mdpi.com/1660-3397/11/11/4451/htm#sthash.TkQbBhDy.dpuf

3.3. Smenamide A (1)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2326 ([M + Na]⁺, C₂₈H₃₇ClN₂O₄Na⁺, calcd. 532.2334), m/z 501.2509 ([M + Na]⁺, C₂₈H₃₈ClN₂O₄⁺, calcd. 501.2515); MS isotope pattern: M (100%), M + 1 (32%, calcd. 31.5%), M + 2 (37%, calcd. 36.0%), M + 3 (10%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.2557 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2092 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1384 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1618 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0836 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0472 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; UV (MeOH): λ_max(ε) 287 nm (8200), 246 nm (46000), 225 nm (92000); CD (MeOH): λ_max(Δε) 238 (+33), 219 (−30).

3.4. Smenamide B (2)

Colorless amorphous solid, HRESIMS (positive ion mode, MeOH) m/z 523.2320 ([M + Na]⁺, calcd. for C₂₈H₃₇ClN₂O₄Na⁺ 532.2334), m/z 501.2505 ([M + Na]⁺, calcd. for C₂₈H₃₈ClN₂O₄⁺ 501.2515); MS isotope pattern: M (100%), M + 1 (31%, calcd. 31.5%), M + 2 (36%, calcd. 36.0%), M + 3 (11%, calcd. 10.6%,); HRESIMS/MS (parent ion m/z 523.23, C₂₈H₃₇ClN₂O₄Na⁺): m/z 487.25567 (C₂₈H₃₆N₂O₄Na⁺, calcd. 487.2567), 397.2091 (C₂₁H₃₀N₂O₄Na⁺, calcd. 397.2098), 320.1383 (C₁₆H₂₄ClNO₂Na⁺, calcd. 320.1388), 284.1617 (C₁₆H₂₃NO₂Na⁺, calcd. 284.1621), 244.0941 (C₁₂H₁₅NO₃Na⁺, calcd. 244.0944), 226.0835 (C₁₂H₁₃NO₂Na⁺, calcd. 226.0838), 202.0471 (C₉H₉NO₃Na⁺, calcd. 226.0475); ¹H and ¹³C NMR: Table 1; ¹H and ¹³C NMR: Supplementary Table S1; UV (MeOH): λ_max(ε) 287 nm (15000), 248 nm (42000), 225 nm (84000); CD (MeOH): λ_max(Δε) 237 (+7.3).

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Smenamides A and B

Smenamides A and B

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).

Structures of smenamide A (1) and B (2).