8000
M. E. Zhidkov et al. / Tetrahedron Letters 48 (2007) 7998–8000
Hormann, A.; Chaudhuri, B.; Fretz, H. Bioorg. Med.
Chem. 2001, 9, 917–921.
3. Segraves, N. L.; Robinson, S. J.; Garcia, D. J. Nat. Prod.
2004, 67, 783–792.
4. Radchenko, O. S.; Novikov, V. L.; Elyakov, G. B.
Tetrahedron Lett. 1997, 38, 5339–5342.
dibromofascaplysin 5 are being investigated thoroughly.
It has already been shown by flow cytometry that com-
pounds 3 and 4 induced apoptosis in human leukemia
HL-60 cells at low concentrations of 0.25 lM: 35.8%
and 36.1% of the apoptotic cells compared to untreated
control cells.
5. Compound 9: white needles; mp 141–142 °C; IR (KBr)
mmax
: ;
2965, 1708, 1658, 1581, 1468 cmꢀ1 1H NMR
We intend to apply this approach to the formation of
12H-pyrido[1,2-a:3,4-b0]diindole ring systems to synthe-
size various fascaplysin derivatives, that, in turn, will
open up fresh opportunities for detailed studies of the
structure activity relationships among these potentially
physiologically active substances.
(250 MHz, CDCl3) d: 7.75 (d, J = 1.9 Hz, 1H), 7.42 (dd,
J1 = 8.3 Hz, J2 = 1.9 Hz, 1H), 7.17 (d, J = 8.3 Hz, 1H),
3.79 (s, 2H, –CH2–); 13C NMR (75 MHz, CDCl3) d: 175.8,
135.2, 132.6, 132.5, 130.8, 125.7, 122.0, 40.7; MS (APCI):
m/z = 293/295/297 (50.9:100.0:49.5) (M+H)+. Anal. Calcd
for C8H6O2Br2: C, 32.69; H, 2.06. Found: C, 32.62; H, 2.08.
6. Santos, L. S.; Pilli, R. A.; Rawal, V. H. J. Org. Chem. 2004,
69, 1283–1289.
7. For example, compound 10: white solid; mp 119–120 °C;
Acknowledgments
IR (KBr) mmax: 3366, 3284, 3081, 2944, 1650, 1627, 1614,
1
1580, 1563, 1468 cmꢀ1; H NMR (250 MHz, DMSO-d6) d:
The research described in this publication was made pos-
sible in part by the award No. RUXO-003-VL-06 from
the U.S. Civilian Research & Development Foundation
for the Independent States of the Former Soviet Union
(CRDF) and the Russian Ministry of Education and
Science. This work was also supported by a Grant from
the Program of Presidium of RAS ‘Molecular and Cell
Biology, FEBRAS Grant 06-III-A-05-122, Grant of the
Russian Foundation for Basic Research (No. 04-48246)
and Grant of President of RF for the Support of the
Leading Science School (No. 6491.2006.4).
10.81 (br s, 1H, NH), 8.14 (t, J = 5.9 Hz, 1H, NHCO), 7.82
(d, J = 2.2 Hz, 1H), 7.52 (d, J = 8.1 Hz, 1H), 7.51 (dd,
J1 = 8.1 Hz, J2 = 2.2 Hz, 1H), 7.33 (d, J = 8.1 Hz, 1H),
7.26 (d, J = 8.1 Hz, 1H), 7.14 (d, J = 2.2 Hz, 1H), 7.06 (td,
J1 = 6.8 Hz, J2 = 8.1 Hz, J3 = 1.2 Hz, 1H), 6.97 (td,
J1 = 6.8 Hz, J2 = 8.1 Hz, J3 = 1.2 Hz, 1H), 3.56 (s, 2H,
–CH2–CO), 3.35 (q, J1 = 7.3 Hz, 2H, CH2–NH), 2.83 (t,
J = 7.3 Hz, 2H, CH2–CH2–NH); 13C NMR (75 MHz,
CDCl3) d: 169.4, 136.4, 134.9, 133.0, 131.7, 129.0, 127.9,
127.2, 124.9, 122.1, 122.0, 119.4, 118.6, 112.7, 111.2, 44.1,
39.8, 33.9; MS (APCI) m/z = 435/437/439 (50.5:100.0:50.7)
(M+H)+. Anal. Calcd for C18H16N2OBr2: C, 49.57; H,
3.70; N, 6.42. Found: C, 49.67; H, 3.72; N, 6.48.
8. For example, compound 13: yellow solid; mp 174–175 °C;
IR (KBr) mmax: 3292, 3061, 1657, 1625, 1576, 1494,
References and notes
1463 cmꢀ1 1H NMR (250 MHz, DMSO-d6) d: 10.45 (br
;
s, 1H, NH), 8.48 (d, J = 4.9 Hz, 1H), 8.44 (d, J = 4.9 Hz,
1H), 8.34 (d, J = 7.9 Hz, 1H), 8.02 (d, J = 1.9 Hz, 1H), 7.85
(d, J = 8.3 Hz, 1H), 7.77 (dd, J1 = 8.3 Hz, J2 = 1.9 Hz, 1H),
7.64 (td, J1 = 7.2 Hz, J2 = 8.0, Hz, J3 = 1.0 Hz, 1H), 7.57
(d, J = 8.0 Hz, 1H), 7.34 (td, J1 = 7.2 Hz, J2 = 7.9 Hz,
J3 = 1.0 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) d: 195.9,
141.9, 140.5, 137.9, 135.3, 134.8, 134.3, 131.3, 131.0, 130.3,
129.2, 123.2, 121.9, 120.5, 120.0, 119.8, 113.1; MS (APCI)
m/z = 429/431/433 (50.5:100.0:50.6) (M+H)+. Anal. Calcd
for C18H10N2OBr2: C, 50.27; H, 2.34; N, 6.51. Found: C,
50.37; H, 2.36; N, 6.60.
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Popov, A. M.; Stonik, V. A. Antibiot. Khimioter. 1991, 36,
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