ANTI-TUMOR ACTIVITY OF MONOCARBONYL CURCUMIN ANALOGS
45
temperature and the mixture extracted with ethyl
A-115 - (2E,5E)-2,5-bis(3-Methoxy-4-((3-
methylbut-2-en-1-yl)oxy)benzylidene)
cyclopentanone
acetate (50 mL33) and the organic phase was
washed with H2O, dried over anhydrous MgSO4 and
the solvent evaporated to dryness. The crude product
was purified by column chromatography eluting with
petroleum ether and ethyl acetate to afford A110,
A113, B110, B113, and B114.
Orange powder, 98.9% yield, mp 148.2-148.68C.
1H-NMR (CDCl3) d:1.754-1.785(12H, m, ACH334),
3.113 (4H, s, CH2ACH2), 3.917 (6H, s, AOCH332),
4.645 (4H, d, J 5 6.6 HZ, AOCH2 32), 5.522 (2H, t,
ACH@C 32), 6.935 (2H, d, J 5 8.4 HZ, ArAH532),
7.135 (2H, s, ArAH232), 7.205 (2H, d, J 5 8.4 HZ,
ArAH632), 7.542(2H, s, ArACH@32). ESI-MS m/z:
489.1(M1H)1, calculated for C31H36O5: 488.26.
A110 - ((1E,1’E)-(2-Oxocyclopentane-1,3-
diylidene)bis(methanylylidene))bis(2-methoxy-4,1-
phenylene) dibenzoate
Yellow powder, 64.5% yield, mp 193.7–194.98C.
1H-NMR (CDCl3) d: 3.163 (4H, s, CH2ACH2), 3.855
(6H, s, AOCH3), 7.243 (2H, d, J 5 9.0 HZ, ArAH5),
A-116 - (2E,5E)-2,5-bis(3-Methoxy-4-
propoxybenzylidene)cyclopentanone
7.25 (2H, s, ACH@C), 7.282 (2H, 0d, J 5 8.4 HZ, Ar-
Yellow powder, 68.5% yield, mp 112.2-114.28C.
1H-NMR (CDCl3) d: 1.043 (6H, t, ACH332), 1.877-
1.913 (4H, m, ACH2A32), 3.112 (4H, s,
CH2ACH2), 3.865 (6H, s, AOCH332), 4.038 (4H, t,
AOCH232), 6.933 (2H, d, J 5 8.4 HZ, ArAH532),
7.140 (2H, s, ArAH232), 7.211(2H, d, J 5 8.4 HZ,
ArAH632), 7.541 (2H, s, ArACH@ 32). ESI-MS m/
z: 437.1(M1H)1, calculated for C27H32O5: 436.22.
0
H6), 7.483–7.540 (4H, m, ArAH3 ,5 ), 7.609 (2H, s,
0
ArAH2), 7.659(2H, d, J 5 7.2 HZ, ArAH4 ), 8.212-
0
0
8.236
(4H,
m,
ArAH2 ,6 ).
ESI-MS
m/z:
561.1(M1H)1, calculated for C35H28O7: 560.18.
A-111 - (2E,5E)-2,5-bis(4-(2-Hydroxyethoxy)-3-
methoxybenzylidene)cyclopentanone
Yellow powder, 73.6% yield, mp 185.3–187.88C.
1H-NMR (CDCl3) d: 3.108 (4H, s, CH2ACH2), 3.917
(6H, s, AOCH332), 3.991 (4H, t, AOCH2 32),
4.185 (4H, t, AOCH2 32), 6.974 (2H, d, J 5 7.8 HZ,
ArAH532), 7.133(2H, s, ArAH2 32), 7.208(2H, d,
J 5 7.8 HZ, ArAH632), 7.535 (2H, s, ArACH@32).
ESI-MS m/z: 441.0(M1H)1, calculated for
C25H28O7: 440.18.
B-110 - ((1E,4E)-3-Oxopenta-1,4-diene-1,5-
diyl)bis(2-methoxy-4,1-phenylene)dibenzoate
Yellow powder, 56.2% yield, mp 234.0–235.78C.
1H-NMR (CDCl3) d: 3.88 (6H, s, AOCH332), 7.02
(2H, d, J 5 15.6 Hz, COACH@), 7.23 (2H, d,
ArAH5), 7.280 (2H, d, ArAH6), 7.53 (4H, t, J 5 7.8
0
HZ, ArAH3 ,5 ), 7.61 (2H, s, ArAH2), 7.65 (2H, t,
0
J 5 7.8 HZ, ArAH4 ), 7.71 (2H, d, J 5 15.6 HZ,
0
0
ArACH@), 8.23 (4H, d, ArAH2 ,6 ). ESI-MS m/z:
535.0(M1H)1, calculated for C33H26O7: 534.17.
A-112 - (2E,5E)-2,5-bis(4-(Cyclopentyloxy)-3-
methoxybenzylidene)cyclopentanone
Yellow powder, 45.3% yield, mp 114.0–116.28C.
0
0
1H-NMR (CDCl3) d: 1.58 (8H, m, H3 ,4 ), 2.23 (8H,
B-111 - (1E,4E)-1,5-bis(4-(2-Hydroxyethoxy)-3-
methoxyphenyl)penta-1,4-dien-3-on
0
0
0
m, H2 ,5 ), 3.81 (2H, s, H1 ), 3.91 (6H, s, AOCH332),
3.10 (4H, s, CH2ACH2), 6.96 (2H, d, J 5 7.8 HZ,
ArAH5), 7.20 (2H, d, J 5 7.8 HZ, ArAH6), 7.27 (2H,
s, ArAH2), 7.53 (2H, s, ArACH@]). ESI-MS m/z:
489.1 (M1H)1, calculated for C31H36O5: 488.26.
Yellow powder, 75.4% yield, mp 91.2–93.68C.
1H-NMR (DMSO) d: 3.344 (6H, s, AOCH332),
3.387 (2H, s, AOH), 3.73 (4H, t, J 5 5.4 HZ,
CH2ACH2), 4.03 (4H, t, J 5 4.8 HZ, AOCH2), 7.03
(2H, d, J 5 15.6 HZ, COACH@), 7.17 (2H, d,
ArAH5), 7.29 (2H, d, ArAH6), 7.49 (2H, s, ArAH2),
7.71 (2H, d, J 5 15.6 HZ, ArACH@). ESI-MS m/z:
437.0(M1Na)1, calculated for C23H26O7: 414.17.
A-113- (1E,1’E)-(2-Oxocyclopentane-1,3-
diylidene)bis(methanylylidene))bis (2-methoxy-4,1-
phenylene) diacetate
Yellow powder, 92.0% yield, mp 200.6-201.88C.
1H-NMR (CDCl3) d: 2.337 (6H, s, COACH332),
3.110 (4H, s, CH2ACH2), 3.884 (6H, s, AOCH332),
7.110 (2H, d, J 5 7.8 HZ, ArAH532), 7.173(2H, s,
ArAH232), 7.214 (2H, d, J 5 8.4 HZ, ArAH632),
7.557 (2H, s, ArACH@ 32). ESI-MS m/z: 437.2
B-113 (1E,4E)-3-Oxopenta-1,4-diene-1,5-diyl)bis(2-
methoxy-4,1-phenylene)diacetate
Yellow powder, 60.0% yield, mp 72.8–75.28C .
1H-NMR (CDCl3) d: 2.33 (6H, s, ACOCH332), 3.88
(6H, s, AOCH3 32), 7.03 (2H, d, J 5 15.6 HZ,
(M1H)1, 459.2 (M1Na)1, calculated for C25H24O7: ACOCH@ 32), 7.11 (2H, d, J 5 7.8 HZ, ArAH532),
436.15.
7.22 (2H, d, J 5 8.4 HZ, ArAH6 32), 7.27 (2H, s,
Drug Dev. Res.