A. C. Giddens et al. / Tetrahedron Letters 46 (2005) 7355–7357
7357
5.1 Hz, H-50), 7.34 (1H, s, H-4), 7.24 (1H, dd, J = 8.1,
1.7 Hz, H-600), 7.17 (1H, d, J = 1.6 Hz, H-200), 6.90 (1H, d,
J = 8.2 Hz, H-500), 6.03 (2H, s, OCH2O); 13C NMR
(300 MHz, CDCl3) d: 158.21 (C-2), 151.93 (C-5), 150.81
(C-60), 148.31 (C-400), 148.23 (C-300), 147.46 (C-20), 133.23
(C-40), 123.72 (C-30), 123.58 (C-50), 122.55 (C-4), 121.76
(C-100), 118.62 (C-600), 108.92 (C-500), 104.91 (C-200), 101.47
(OCH2O); HREIMS m/z 266.0694 (calcd for C15H10N2O3:
266.0691).
Acknowledgements
This work was supported by a grant from the Maurice &
Phyllis Paykel Trust. A.C.G. wishes to thank the Uni-
versity of Auckland for a UoA Doctoral scholarship.
References and notes
1
13. Spectral data for some key compounds: Compound 8: H
1. Raviglione, M. C. Tuberculosis 2003, 83, 4–14.
2. Espinal, M. A. Tuberculosis 2003, 83, 44–51.
3. Copp, B. R. Nat. Prod. Rep. 2003, 20, 535–557; Okunade,
A. L.; Elvin-Lewis, M. P. F.; Lewis, W. H. Phytochemistry
2004, 65, 1017–1032.
4. Dominguez, X. A.; de la Fuente, G.; Gonzalez, A. G.;
Reina, M.; Timon, I. Heterocycles 1988, 27, 35–38.
5. Rastogi, N.; Abaul, J.; Goh, K. S.; Devallois, A.;
NMR (300 MHz, CDCl3) d: 9.35 (1H, d, J = 1.7 Hz, H-
20), 8.70 (1H, dd, J = 4.9, 1.6 Hz, H-60), 8.37 (1H, dt,
J = 8.1, 1.8 Hz, H-40), 7.73 (2H, m, H-200, H-600), 7.49–7.36
(5H, m, H-4, H-50, H-300, H-400, H-500); HREIMS m/z
222.0794 (calcd for C14H10N20: 2220793). Compound 9:
1H NMR (300 MHz, CDCl3) d: 8.11–8.08 (2H, m, H-20,
H-60), 7.71–7.67 (2H, m, H-200, H-600), 7.51–7.38 (6H, m,
H-4, H-30, H-40, H-50, H-300, H-500), 7.30 (1H, m, H-400);
HREIMS m/z 221.0843 (calcd for C15H11NO: 221.0841).
Texamine 10: Mp 134–136.5 °C (lit.4 134–137 °C); 1H
NMR (300 MHz, CDCl3) d: 8.08–8.05 (2H, m, H-20, H-
60), 7.49–7.41 (3H, m, H-30, H-40, H-50), 7.28 (1H, s, H-4),
7.20 (1H, dd, J = 8.1, 1.7 Hz, H-600), 7.14 (1H, d,
J = 1.7 Hz, H-200), 6.85 (1H, d, J = 8.1 Hz, H-500), 5.97
(2H, s, OCH2O); HREIMS m/z 265.0738 (calcd for
C16H11NO3: 265.0739).
`
Philogene, E.; Bourgeois, P. FEMS Immunol. Med. Mic.
1998, 20, 267–273.
6. Lee, J. C.; Bae, Y. H.; Chang, S.-K. Bull. Kor. Chem. Soc.
2003, 24, 407–408.
7. Ackrell, J.; Muchowski, J. M.; Galeazzi, E.; Guzman, A.
J. Org. Chem. 1986, 51, 3374–3376.
8. Bretschneider, H.; Hormann, H. Monatsh. Chem. 1953,
84, 1021–1032.
9. Moriya, T.; Takabe, S.; Maeda, S.; Matsumoto, K.;
Takashima, K.; Mori, T.; Takeyama, S. J. Med. Chem.
1986, 29, 333–341.
14. Collins, L. A.; Franzblau, S. G. Antimicrob. Agents
Chemother. 1997, 41, 1004–1009.
15. Cho, S. H.; Warit, S.; Wan, B.; Di, W.; Hwang, C. H.;
Franzblau, S. G. Low oxygen recovery assay to screen for
compounds active against non-replicating persistent
(NRP)-TB. 2005. Keystone Symposium: Tuberculosis:
Integrating Host and Pathogen Biology, Whistler, British
Columbia, Canada. The low oxygen recovery assay
(LORA) utilizes Mycobacterium tuberculosis H37Rv
(pFCA-luxAB) which is constructed using the Vibrio
harveyii luciferase gene16 on a plasmid construct that
employs the acetamidase promotor17 for enhanced signal.
Full details of the assay will be published elsewhere.
16. Snewin, V. A.; Gares, M. P.; Gaora, P. O.; Hasan, Z.;
Brown, I. N.; Young, D. B. Infect. Immun. 1999, 67, 4586–
4593.
10. When stronger bases (e.g. NaOH) were utilized in an
attempt to increase the solubility of nicotinoylchloride
hydrochloride (6), complex mixtures were produced.
Subsequent use, under identical reaction conditions, of
benzoyl chloride in the preparation of analogue 10
afforded the corresponding amide in 52% yield further
supporting poor substrate solubility as the cause of the
low yield of 7.
11. Godfrey, A. G.; Brooks, D. A.; Hay, L. A.; Peters, M.;
McCarthy, J. R.; Mitchell, D. J. Org. Chem. 2003, 68,
2623–2632.
12. Spectral data for Texaline (1): Mp 167–169 °C (lit.4 171–
174 °C); 1H NMR (300 MHz, CDCl3) d: 9.31 (1H, d,
J = 1.8 Hz, H-20), 8.68 (1H, dd, J = 4.9, 1.6 Hz, H-60),
8.33 (1H, dt, J = 8.0, 1.9 Hz, H-40), 7.41 (1H, dd, J = 7.7,
17. Changsen, C.; Franzblau, S. G.; Palittapongarnpim, P.
Antimicrob Agents Chemother. 2003, 47, 3682–3687.