6416
B. A. Shah et al. / Bioorg. Med. Chem. Lett. 17 (2007) 6411–6416
3. Ammon, H. P.; Safayhi, H.; Mack, T.; Sabieraj, J.
J. Ethnopharmacol. 1993, 38, 113.
4. Mahajan, B.; Sethi, V. K.; Taneja, S. C.; Dhar, K. L.
Phytochemistry 1995, 39, 453.
5. Safayhi, H.; Mack, T.; Sabieraj, J.; Anazodo, M. I.;
Subramanian, L. R.; Ammon, H. P. J. Pharmacol. Exp.
Ther. 1992, 261, 1143.
6. Schweizer, S.; von Brocke, A. F.; Boden, S. E.; Bayer, E.;
Ammon, H. P.; Safayhi, H. J. Nat. Prod. 2000, 63, 1058.
7. Safayhi, H.; Sailer, E. R.; Ammon, H. P. Mol. Pharmacol.
1995, 47, 1212.
8. Sharma, M. L.; Bani, S.; Singh, G. B. Int. J. Immuno-
pharmacol. 1989, 11, 647.
9. Singh, S.; Khajuria, A.; Taneja, S. C.; Khajuria, R. K.;
Singh, J.; Qazi, G. N. Bioorg. Med. Chem. Lett. 2007, 17,
3706.
10. Gupta, I.; Parihar, A.; Malhotra, P.; Singh, G. B.; Ludtke,
R.; Safayhi, H.; Ammon, H. P. Eur. J. Med. Res. 1997, 2, 37.
11. Gupta, I.; Parihar, A.; Malhotra, P.; Gupta, S.; Ludtke,
R.; Safayhi, H.; Ammon, H. P. Planta Med. 2001, 67, 391.
12. Gupta, A.; Gupta, V.; Parihar, A.; Gupta, S.; Ludtke, R.;
Safayhi, H.; Ammon, H. P. Eur. J. Med. Res. 1998, 3, 511.
13. Kapil, A.;Moza, N. Int.J. Immunopharmacol.1992, 14, 1139.
14. Safayhi, H.; Mack, T.; Ammon, H. P. Biochem. Pharma-
col. 1991, 41, 1536.
30. Nakamura, H.; Suda, H.; Takita, T.; Auyagi, T.; Umez-
awa, H.; Iitaka, Y. Y. J. Antibiot. 1976, 29, 102.
31. Ino, K.; Goto, S.; Nomura, S.; Isobe, K. I.; Nawa, A.;
Okamoto, T.; Tomoda, Y. Anticancer Res. 1995, 15, 2081.
32. Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson,
G. M. L.; Smith, C. D. J. Org. Chem. 1994, 59, 7219.
33. Schaefer, J. P.; Wheatley, P. J. J. Org. Chem. 1968, 33,
166.
34. Schaefer, J. P.; Wheatley, P. J. J. Chem. Soc., Chem.
Commun. 1967, 578.
35. Grollman, A. P.; Walsh, M. J. Biol. Chem. 1967, 242,
3226.
36. He, A.-W. R.; Cory, J. G. Anticancer Res. 1999, 19, 421.
37. Diacel Chemical Industries Ltd. European Patent Appli-
cation No. 0654 534 A2, November 18, 1994.
38. Wang, Z. M.; Zhang, X. L.; Sharpless, K. B. Tetrahedron
Lett. 1993, 34, 2267.
39. (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev.
1996, 96, 835; (b) Martha, S. R.; Omar, M. M.; Cecilia, A.
P.; Leticia, Q.; Eusebio, J. J. Org. Chem. 2003, 68, 2369.
40. All compounds provided acceptable data and were iden-
tified through 1H NMR and 13C NMR spectroscopy.
Compound 5 (3-a-acetoxy-4-b-isocyanato-24-norurs-12-
ene): white powder, [a]D +8ꢁ (c 0.1 CHCl3). Mp 145–
1
147 ꢁC. H NMR (200 MHz, CDCl3): d 0.82, 0.93, 1.08,
15. Han, R. Stem Cells 1994, 12, 53.
1.12, 1.45 (21H, 7· –CH3), 2.11 (3H, s, –CH3CO), 4.78
(1H, br s, H-3), 5.16 (1H, br s, H-12). 13C NMR (50 MHz,
CDCl3): d 14.4, 17.1, 17.5, 17.9, 21.3, 21.4, 22.5, 23.1, 23.5,
26.6, 28.1, 28.8, 29.5, 31.3, 32.2, 33.3, 34.6, 37.3, 39.4, 39.7,
39.8, 41.5, 42.3, 47.0, 49.9, 59.1, 60.4, 75.6, 124.4, 127.9,
139.6, 170.8. Anal. Calcd for C32H49NO3: C, 77.53; H,
9.96; N, 2.83. Found: C, 77.43; H, 9.99; N, 2.85. ESI-MS
(m/z): 518 [M+Na]+. Compound 9 (3-a-hydroxy-4-b-
amino-24-norurs-12-ene): white powder, [a]D +7.3ꢁ (c 0.1
16. Shashi, B.; Kumar, A.; Malik, F.; Andotra, S. S.; Sethi, V.
K.; Kaur, I.; Taneja, S. C.; Qazi, G. N.; Singh, J.
17. Glaser, T.; Winter, S.; Groscurth, P.; Safayhi, H.; Sailer,
E. R.; Ammon, H. P. Br. J. Cancer 1999, 80, 756.
18. Jannsen, G.; Bode, U.; Breu, H.; Dohm, B.; Engelbrecht,
V.; Gobel, U. Klin. Padiatr. 2000, 212, 189.
19. Winkling, M.; Sarikaya, S.; Rahmanian, A.; Jodicke, A.;
Boker, D. K. J. Neurooncol. 2000, 46, 97.
1
CHCl3). Mp 105–107 ꢁC. H NMR (200 MHz, CDCl3): d
20. Hoernlein, R. F.; Orlikowsky, T.; Zehrer, C.; Nietham-
mer, D.; Sailer, E. R.; Simmet, T.; Dannecker, G. E.;
Ammon, H. P. J. Pharmacol. Exp. Ther. 1999, 288, 613.
21. Jing, Y.; Nakajo, S.; Xia, L.; Nakaya, K.; Fang, Q.;
Waxman, S.; Han, R. Leuk. Res. 1999, 23, 43.
22. Shao, Y.; Ho, C. T.; Chin, C. K.; Badmaev, V.; Ma, W.;
Huang, M. T. Planta Med. 1998, 64, 328.
0.80, 0.91, 1.03, 1.09, 1.19 (21H, 7· –CH3), 3.41 (1H, br s,
H-3), 5.14 (1H, t, J = 3.6 Hz, H-12). 13C NMR (50 MHz,
CDCl3): d 15.5, 17.0, 17.5, 17.6, 21.5, 23.1, 23.4, 24.9, 26.6,
28.1, 28.7, 28.8, 31.3, 32.6, 33.1, 33.8, 36.8, 39.6, 39.7, 40.2,
41.2, 42.3, 47.4, 48.4, 54.5, 59.1, 76.7, 124.4, 139.6. Anal.
Calcd for C29H49NO: C, 81.44; H, 11.55; N, 3.27. Found:
C, 81.34; H, 11.61; N, 3.22. ESI-MS (m/z): 428 [M+H]+.
Compound 29 (3-b-hydroxy-4-b-amino-24-norurs-12-ene):
white powder, [a]D +6.4ꢁ (c 0.1 CHCl3). Mp 211–213 ꢁC.
1H NMR (200 MHz, CDCl3): d 0.80, 0.91, 0.99, 1.05, 1.09,
1.14 (21H, 7· –CH3), 3.16 (2· d, J = 5.10 Hz, 1H, H-3),
5.14 (br s, 1H, H-12). 13C NMR (50 MHz, CDCl3): d 16.5,
17.5, 18.3, 20.4, 20.9, 22.6, 23.2, 25.5, 26.6, 27.0, 27.8, 28.8,
30.2, 30.7, 31.2, 32.7, 36.5, 39.6, 40.4, 40.7, 41.2, 45.5, 47.1,
50.1, 54.7, 58.5, 79.8, 123.4, 139.7. Anal. Calcd for
C29H49NO: C, 81.44; H, 11.55; N, 3.27. Found: C,
81.32; H, 11.65; N, 3.23. ESI-MS (m/z): 428 [M+H]+.
41. Beton, J. L.; Halsall, T. G.; Jones, E. R. H. J. Chem. Soc.
1956, 2904.
23. Syrovets, T.; Buchele, B.; Gedig, E.; Slupsky, J. R.;
Simmet, T. Mol. Pharmacol. 2000, 63, 1058.
24. Liu, J. J.; Nilsson, A.; Oredsson, S.; Badmaev, V.; Zhao,
W. Z.; Duan, R. D. Carcinogenesis 2002, 23, 2087.
25. Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
26. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis:
Construction of Chiral Molecules Using Amino Acids;
Wiley: New York, 1987.
27. Gupta, P.; Shah, B. A.; Parshad, R.; Qazi, G. N.; Taneja,
28. (a) Ms Merrell Pharmaceuticals, WO-9602499, 1996; (b)
Ms DuPont Pharmaceuticals Co., WO-0174784, 2001; (c)
Ms Aventis Pharmaceuticals, WO-0119833, 2001; (d) Ms
Sankyo Co., EP-0543662, 1996.
42. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.;
Paul, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P.;
Wolff, A. V.; Goodrich, M. G.; Campbell, H.; Mayo, J.;
Boyd, M. J. Natl. Cancer Inst. 1991, 83, 757.
29. Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.;
Takeuchi, T. J. Antibiot. 1976, 29, 97.