4
B. E.-D. M. El-Gendy, M. E. Rateb / Bioorg. Med. Chem. Lett. xxx (2015) xxx–xxx
3259, 1675, 1396, 1150, 1028, 911, 751 cmꢁ1
;
1H NMR (400 MHz, CDCl3) dH 7.61
(d, J = 2.1 Hz, 1H), 7.39 (d, J = 8.5 Hz, 1H), 6.93 (d, J = 9.6 Hz, 1H), 6.91 (dd, J = 8.5,
2.2 Hz, 1H), 4.77 (d, J = 9.7 Hz, 1H), 4.14 (dd, J = 11.9, 4.6 Hz, 1H), 4.11 (t,
J = 8.2 Hz, 1H), 3.86 (s, 3H), 3.62 (m, 2H), 3.47 (dd, J = 16.1, 4.7 Hz, 1H), 3.03 (dd,
J = 16.0, 12.0 Hz, 1H), 2.39 (m, 1H), 2.28 (m, 1H), 2.05 (m, 1H), 1.95 (s, 3H), 1.93
(m, 1H), 1.67 (s, 9H), 1.60 (s, 3H); 13C NMR (100 MHz, CDCl3) dC 168.4, 165.9,
157.9, 149.9, 137.2, 136.1, 134.6, 123.2, 121.9, 118.7, 114.3, 111.8, 100.9, 84.3,
59.6, 56.3, 55.8, 50.9, 45.5, 28.5, 28.3, 26.3, 23.3, 21.7, 18.9. HRESIMS m/z
480.2493 [M+H]+ (calculated for C27H34N3O5, 480.2493).
24. (3S,8aS)-tert-Butyl-3-((1-(tert-butoxycarbonyl)-2-(3-methylbut-2-en-1-yl)-1H-
indol-3-yl)methyl)-1,4-dioxohexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxy-
20
late (5a): Orange yellow solid; [
a]
D
ꢁ65 (c 0.70, MeOH); UV (MeOH) kmax (log
e
) at 227 (3.8), 271 (2.7), 290 (3.2) nm; IR (CH2Cl2)
m
max 3269, 2977, 1732, 1677,
1478, 1161, 1029, 710 cmꢁ1
;
1H NMR (400 MHz, CDCl3) dH 8.02 (d, J = 8.3 Hz,
1H), 7.50 (d, J = 8.3 Hz, 1H), 7.21 (t, J = 7.5 Hz, 1H), 7.16 (t, J = 7.5 Hz, 1H), 5.14 (t,
J = 5.2 Hz, 1H), 4.97 (dd, J = 4.7, 2.3 Hz, 1H), 3.85 (q, 1H), 3.74 (dd, J = 16.0, 5.4 Hz,
1H), 3.56 (dd, J = 15.2, 2.5 Hz, 1H), 3.51 (m, 1H), 3.47 (dd, J = 15.1, 5.1 Hz, 1H),
3.37 (dd, J = 16.1, 6.1 Hz, 1H), 2.96 (m, 1H), 1.71 (m, 1H), 2.01 (s, 3H), 1.64 (s,
18H), 1.57 (s, 3H), 1.35 (m, 1H), 0.0 (m, 1H), ꢁ0.08 (m, 1H); 13C NMR (100 MHz,
CDCl3) dC 165.8, 164.2, 151.4, 150.2, 140.4, 136.1, 132.8, 129.6, 124.1, 122.5,
121.5, 119.4, 115.0, 111.8, 84.1, 84.0, 61.0, 60.5, 44.7, 28.3, 28.2, 28.1, 27.7, 26.2,
25.8, 20.4, 18.4. HRESIMS m/z 452.2539 [M+H]+ (calculated for C26H34N3O4,
452.2544).
18. Taxonomic identification of the fungal strain was achieved by extraction of
gDNA from a freshly prepared fungus on malt extract sea salt broth and DNA
amplification and sequencing of the fungal internal transcribed spacer (ITS)
region using the universal primers ITS1 (50-TCCGTAGGTGAACCTGCGG-30) and
ITS4 (50-TCCTCCGCTTATTGATATGC-30) according to Kjer’s protocol.29 Quality
and integrity of the extracted DNA were screened by electrophoresis on 1% (w/v)
agarose gel. Sequence thus obtained was submitted to GenBank, National
Centre for Biotechnology Information (NCBI) with accession numbers
KF281606. Alignment with published sequences in GenBank showed that the
fungal isolate MR2012 had 99% identity with Aspergillus fumigatus. The fungal
isolate MR2012 was deposited in the Marine Biodiscovery Centre, University of
Aberdeen, Scotland, UK under the code MBC-MR2012.
28. tert-Butyl-3-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)-
20
1H-indole-1-carboxylate (6a): Colorless solid; [
(MeOH) kmax (log
1697, 1266, 1121, 705 cmꢁ1
a
]
D
ꢁ19 (c 0.80, MeOH); UV
e
) at 224 (3.5), 277 (2.7), 285 (3.1) nm; IR (CH2Cl2) mmax 3269,
;
1H NMR (400 MHz, CDCl3) dH 8.15 (br s, 1H), 7.52
(d, J = 8.0 Hz, 1H), 7.36 (t, J = 7.8 Hz, 1H), 7.26 (t, J = 7.6 Hz, 1H), 4.38 (dd, J = 11.2,
2.4 Hz, 1H), 4.10 (t, J = 8.6 Hz, 1H), 3.73 (ddd, J = 15.3, 3.7, 1.4 Hz, 1H), 3.67
(m,1H), 3.60 (m, 1H), 2.90 (dd, J = 15.2, 11.1 Hz, 1H), 2.09 (m, 1H), 2.06 (m, 1H),
1.92 (m, 1H), 1.68 (s, 9H); 13C NMR (100 MHz, CDCl3) dC 169.5, 165.2, 150.2,
135.1, 125.3, 124.6, 123.0, 118.8, 115.8, 114.9, 106.6, 84.3, 59.4, 54.1, 45.7, 28.5,
28.4, 26.8, 22.8. HRESIMS m/z 384.1920 [M+H]+ (calculated for C21H26N3O4,
384.1918).
23. (5aS,12S,14aS)-tert-Butyl-9-methoxy-12-(2-methylprop-1-en-1-yl)-5,14-dioxo-
2,3,5,5a,6,12,14,14a-octahydropyrrolo[100,200:40,50]pyrazino[10,20:1,6]pyrido
20
[3,4b]indole-11(1H)-carboxylate (4a): Yellow solid; [
UV (MeOH) kmax (log
a
]
D
ꢁ25 (c 0.50, MeOH);
e
) at 226 (3.8), 272 (2.9), 295 (2.1) nm; IR (CH2Cl2) mmax
Please cite this article in press as: El-Gendy, B. E.-D. M. ; Rateb, M. E. Bioorg. Med. Chem. Lett. (2015), http://dx.doi.org/10.1016/