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Organic Letters

Volumn 10, Issue 23, 2008, Pages 5465-5468

Cylindradines A and B: Novel bromopyrrole alkaloids from the marine Sponge axinella cylindratus

(5) Kuramoto, Makoto a Miyake, Norimichi a Ishimaru, Yoshihisa a Ono, Noboru a Uno, Hidemitsu a

a EHIME UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYLINDRADINE A; CYLINDRADINE B; PYRROLE DERIVATIVE;

ANIMAL; ARTICLE; AXINELLA; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; ISOLATION AND PURIFICATION; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TUMOR CELL LINE; IC50;

ALKALOIDS; ANIMALS; AXINELLA; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MICE; PYRROLES;

EID: 61349119320 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol802263j Document Type: Article

Times cited : (41)

References (27)

1
- 0035136516
- Al-Mourabit, A.; Potier, P. Eur. J. Org. Chem. 2001, 237-243.
- (2001) Eur. J. Org. Chem , pp. 237-243
- Al-Mourabit, A.¹ Potier, P.²

2
- 4344678685
- Gautschi, J. T.; Whitman, S.; Holman, T. R.; Crews, P. J. Nat. Prod. 2004, 67, 1256-1261.
- (2004) J. Nat. Prod , vol.67 , pp. 1256-1261
- Gautschi, J.T.¹ Whitman, S.² Holman, T.R.³ Crews, P.⁴

3
- 0017571638
- (a) Sharma, G.; Magdoff-Fairchild, B. J. Org. Chem. 1977, 42, 4118-4124.
- (1977) J. Org. Chem , vol.42 , pp. 4118-4124
- Sharma, G.¹ Magdoff-Fairchild, B.²

4
- 45949131479
- (b) De Nanteuil, G.; Ahond, A.; Guilhem, J.; Poupat, C.; Tran, H. D. E.; Potier, P.; Pusset, M.; Pusset, J.; Laboute, P. Tetrahedron 1985, 41, 6019-6033.
- (1985) Tetrahedron , vol.41 , pp. 6019-6033
- De Nanteuil, G.¹ Ahond, A.² Guilhem, J.³ Poupat, C.⁴ Tran, H.D.E.⁵ Potier, P.⁶ Pusset, M.⁷ Pusset, J.⁸ Laboute, P.⁹

5
- 0001266891
- Fedoreyev, S. A.; Utikina, M. K.; Reshetnyak, M. V.; Maximov, O. B. Tetrahedron Lett. 1986, 27, 3177-3180.
- (1986) Tetrahedron Lett , vol.27 , pp. 3177-3180
- Fedoreyev, S.A.¹ Utikina, M.K.² Reshetnyak, M.V.³ Maximov, O.B.⁴

6
- 0031019142
- Pettit, G. E.; McNuty, J.; Herald, D. L.; Doubek, D. L.; Chpuis, J.-C.; Schmidt, J. M.; Tackett, L. P.; Boyd, M. R. J. Nat. Prod. 1997, 60, 180-183.
- (1997) J. Nat. Prod , vol.60 , pp. 180-183
- Pettit, G.E.¹ McNuty, J.² Herald, D.L.³ Doubek, D.L.⁴ Chpuis, J.-C.⁵ Schmidt, J.M.⁶ Tackett, L.P.⁷ Boyd, M.R.⁸

7
- 85008131292
- Kitagawa, I.; Kobayashi, M.; Kitanaka, K.; Kido, M.; Kyogoku, Y. Chem. Pharm. Bull. 1983, 31, 2321-2328.
- (1983) Chem. Pharm. Bull , vol.31 , pp. 2321-2328
- Kitagawa, I.¹ Kobayashi, M.² Kitanaka, K.³ Kido, M.⁴ Kyogoku, Y.⁵

8
- 0000474502
- Braekman, J.-C.; Daloze, D.; Stoller, C.; Van Soest, R. W. Biochem. Syst. Ecol. 1992, 20, 417-431.
- (1992) Biochem. Syst. Ecol , vol.20 , pp. 417-431
- Braekman, J.-C.¹ Daloze, D.² Stoller, C.³ Van Soest, R.W.⁴

9
- 4143115664
- Tarvert, N.; Al-Mourabit, A. J. Am. Chem. Soc. 2004, 126, 10252-10253.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 10252-10253
- Tarvert, N.¹ Al-Mourabit, A.²

10
- 0033603312
- Andrade, P.; Willoughby, R.; Pomponi, S. A.; Kerr, R. G. Tetrahedron Lett. 1999, 40, 4775-4778.
- (1999) Tetrahedron Lett , vol.40 , pp. 4775-4778
- Andrade, P.¹ Willoughby, R.² Pomponi, S.A.³ Kerr, R.G.⁴

11
- 0000189135
- Foley, L. H.; Büchi, G. J. Am. Chem. Soc. 1982, 104, 1776-1777.
- (1982) J. Am. Chem. Soc , vol.104 , pp. 1776-1777
- Foley, L.H.¹ Büchi, G.²

12
- 0037043548
- (a) Poullennec, K. G.; Kelly, A. T.; Romo, D. Org. Lett. 2002, 4, 2645-2648.
- (2002) Org. Lett , vol.4 , pp. 2645-2648
- Poullennec, K.G.¹ Kelly, A.T.² Romo, D.³

13
- 41249086158
- (b) Wang, S.; Romo, D. Angew. Chem., Int. Ed. 2008, 47, 1284-1285.
- (2008) Angew. Chem., Int. Ed , vol.47 , pp. 1284-1285
- Wang, S.¹ Romo, D.²

14
- 33749260114
- (a) Sato, S.; Kuramoto, M.; Ono, N. Tetrahedron Lett. 2006, 47, 7871-7873.
- (2006) Tetrahedron Lett , vol.47 , pp. 7871-7873
- Sato, S.¹ Kuramoto, M.² Ono, N.³

15
- 0031925012
- (b) Kuramoto, M.; Hayashi, K.; Yamaguchi, K.; Yada, M.; Tsuji, T.; Uemura, D. Bull. Chem. Soc. Jpn. 1998, 71, 771-779.
- (1998) Bull. Chem. Soc. Jpn , vol.71 , pp. 771-779
- Kuramoto, M.¹ Hayashi, K.² Yamaguchi, K.³ Yada, M.⁴ Tsuji, T.⁵ Uemura, D.⁶

16
- 0029942922
- (c) Kuramoto, M.; Chou, T.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867-3880.
- (1996) Tetrahedron Lett , vol.37 , pp. 3867-3880
- Kuramoto, M.¹ Chou, T.² Yamada, K.³ Chiba, T.⁴ Hayashi, Y.⁵ Uemura, D.⁶

17
- 32644447581
- (a) Forenza, S.; Minale, L.; Ricco, R.; Fattorusso, E. J. Chem. Soc., Chem. Commun. 1971, 1129-1130.
- (1971) J. Chem. Soc., Chem. Commun , pp. 1129-1130
- Forenza, S.¹ Minale, L.² Ricco, R.³ Fattorusso, E.⁴

18
- 0002379568
- (b) Garcia, E. E.; Benjamine, L. E.: Fryer, R. I. J. Chem. Soc., Chem. Commun. 1973, 78-79.
- (1973) J. Chem. Soc., Chem. Commun , pp. 78-79
- Garcia, E.E.¹ Benjamine, L.E.² Fryer, R.I.³

19
- 61349146086
- Cylindradine A (1, colorless glass; [α]D -75.3° (c 0.10, MeOH, FABMS m/z, 338, 390, 392 (intensity ratio, 1:2:1, IR (KBr) 3400-3100, 1697, 1637 cm-1; UV λ max (CH3OH) 244 nm (ε 4779, 270 nm (ε 1503, 1H NMR (CD3OD) δ 2.06-2.15 (2H, m, H12, 2.23-2.41 (2H, m, H11, 3.54-3.75 (2H, m, H13, 5.25 (IH, s, H6, 13C NMR (CD3OD) δ 21.3 (C 12, 41.7 (CIl, 46.6 (C13, 56.5 (C6, 85.9 (C10, 98.3 (C3, 107.3 (C2, 113.9 (C4, 134.6 (C5, 159.4 (C8, 161.6 (C 15, Cylindradine B (2, colorless glass; [α]D +59.1° (c 1.49, MeOH, FABMS m/z, 420, 422, 424 (intensity ratio, 1:2:1, IR (KBr) 3500-3000, 1689, 1655, 1630 cm-1; UV λmax (CH 3OH) 242 nm (ε 3166, 275 nm (ε 1266, 1H NMR (CD 3OD) δ 3.63 (1H, d, J, 12.5 Hz, H13a, 3.87 1H, dd, J, 4.6
- 3OD) δ 52.0 (C6), 54.6 (C13). 74.0 (C 12), 80.5 (C11), 88.1 (C10), 98.2 (C3), 107.1 (C2), 113.6 (C4), 134.1 (C5), 159.0 (C8), 162.1 (C15).

20
- 84965822602
- Alley, M. C; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589-601.
- (1988) Cancer Res , vol.48 , pp. 589-601
- Alley, M.C.¹ Scudiero, D.A.² Monks, A.³ Hursey, M.L.⁴ Czerwinski, M.J.⁵ Fine, D.L.⁶ Abbott, B.J.⁷ Mayo, J.G.⁸ Shoemaker, R.H.⁹ Boyd, M.R.¹⁰

21
- 32644447581
- Forenza, S.; Minale, L.; Ricco, R.; Fattorusso, E. Chem. Commun. 1971, 1129-1130.
- (1971) Chem. Commun , pp. 1129-1130
- Forenza, S.¹ Minale, L.² Ricco, R.³ Fattorusso, E.⁴

22
- 0003391883
- 3rd ed, VCH: Weinheim. NY
- Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy, 3rd ed.; VCH: Weinheim. NY, 1990; pp 313-325.
- (1990) Carbon-13 NMR Spectroscopy , pp. 313-325
- Breitmaier, E.¹ Voelter, W.²

23
- 0034366544
- (a) Xu, S.-H; Cen, Y.-Z.; Zeng, L.-M.; Su, J.-Y. Youji Huaxue 2000, 20, 248-250.
- (2000) Youji Huaxue , vol.20 , pp. 248-250
- Xu, S.-H.¹ Cen, Y.-Z.² Zeng, L.-M.³ Su, J.-Y.⁴

24
- 0029905736
- (b) Fu, X.; Ng, P.-L.; Schmitz, F. J.; Hossain, M. B.; van der Helm, D.; Kelly-Borges, M. J. Nat. Prod. 1996, 59, 1104-1106.
- (1996) J. Nat. Prod , vol.59 , pp. 1104-1106
- Fu, X.¹ Ng, P.-L.² Schmitz, F.J.³ Hossain, M.B.⁴ van der Helm, D.⁵ Kelly-Borges, M.⁶

25
- 61349137429
- Crystallographical data: Cylindradine A (1, crystal formula, C 11H12Br2N5O+· CF3CO2-·H3OH; 0.30 × 0.15 × 0.02 mm3; triclinic, space group P-I; a= 8.422(2, b, 9.324 (4, c, 13.223(6) Å, α, 70.298(18)°, β= 85.55(2)°, γ, 75.751(19)°, V= 947.5(8) Å; Mo Kα, T= 150 K, Z, 2, ρcaled, 1.876 g cm-3, μ, 4.338 mm1, F(000, 528, 13492 measured, 4316 unique, 2563 observed [I > 2σ(I, R 1, 0.0790 [I > 2σ(I, wR2= 0.2370 (all, GOF, 1.006. CCDC-702691. Cylindradine B 2, crystal formula, C 11H12Br2N5O3 +·CF3CO2-·H 2O; 0.27 × 0.10
- 2 = 0.1700 (all); GOF = 1.062. CCDC-702692. Structures of cylindradines in CIF format have been deposited in CCDC.

26
- 0034474897
- Flack, H. D.; Bernardinelli, G. J. Appl Crystallogr. 2000, 33, 1143-1148.
- (2000) J. Appl Crystallogr , vol.33 , pp. 1143-1148
- Flack, H.D.¹ Bernardinelli, G.²

27
- 18444363346
- Xu, S.-H.; Liao, X.-J.; Zeng, X.-C.; Yang, K.; He, D.-H.; Yu, K.-B. Acta Crystallogr. 2004, E60, o782-o783.
- (2004) Acta Crystallogr , vol.E60
- Xu, S.-H.¹ Liao, X.-J.² Zeng, X.-C.³ Yang, K.⁴ He, D.-H.⁵ Yu, K.-B.⁶

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