C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity
Table 1
CM reactions of C-allyl glycosides (1a–1h) and exo-glycal (1i) with 7-O-allylgenistein (2).
Entry
Sugar
Glycoconjugate Yieldsa
C-Allyl glycoside homodimer Yields (%)a
7-O-Allylgenistein homodimer Yields (%)b
1
1a
3a 42% (2.5) 25% (10)d
4a 7% (2.5) 18% (only E)d
5 57% (2.0) 47% (11.4)d
2
1b
3b 41% (2.1)
4b 29% (1.8)
5 36% (2.0)
3
1c
3c 44% (2.2)
4c 30% (n.d.)
5 43% (2.0)
4
1d
3d 18% (2.6)
4d 6% (2.0)
5 30% (2.0)
5
1e
3e 33% (2.1)
4e 9% (1.5)
5 47% (2.0)
6
1f
3f 20% (2.2)
4f 8% (1.6)
5 13% (2.0)
7
1g
3g 4% (2.4)
4g 13% (1.5)
5 28% (2.0)
8
1h
3h 35% (2.8) 17% (7.3)d
4h 26% (2.4) 5% (only E)d
5 29% (2.0) 18% (11.4)d
9
1i
—
—
5 21% (2.0)
Yields calculated according to initial amount of C-allyl glycoside.
bYields calculated according to initial amount of allylgenistein.
c molar ratio was calculated from 1H NMR spectra.
dCM reactions initiated by II generation Grubbs complex.