Research Article

C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity

Table 1

CM reactions of C-allyl glycosides (1a1h) and exo-glycal (1i) with 7-O-allylgenistein (2).

EntrySugarGlycoconjugate
Yieldsa
C-Allyl glycoside homodimer
Yields (%)a
7-O-Allylgenistein homodimer
Yields (%)b

11a3a
42% (2.5)  
25% (10)d
4a
7% (2.5)  
18% (only E)d
5
57% (2.0)  
47% (11.4)d
21b3b
41% (2.1)
4b
29% (1.8)
5
36% (2.0)
31c3c
44% (2.2)
4c
30% (n.d.)
5
43% (2.0)
41d3d
18% (2.6)
4d
6% (2.0)
5
30% (2.0)
51e3e
33% (2.1)
4e
9% (1.5)
5
47% (2.0)
61f3f
20% (2.2)
4f
8% (1.6)
5
13% (2.0)
71g3g
4% (2.4)
4g
13% (1.5)
5
28% (2.0)
81h3h
35% (2.8)  
17% (7.3)d
4h
26% (2.4)  
5% (only E)d
5
29% (2.0)  
18% (11.4)d
91i5
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.