LETTER
Combretastatin A-4 Analogues
1207
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Table 1 Yields and Cytotoxicity of Combretastatin A-4 Analogues
Ar2
Product
Yield
(%)
IC50
(μM)
OH
F
55a
51
4a (CA-4)
0.002
0.007
OMe
OMe
4b
Cl
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Hadfield, J. A.; McGown, A. T.; Pritchard, R. G. Synthesis
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1961, 83, 3834.
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O.; Brion, J.-D.; Alami, M. Synthesis 2007, 2025.
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48, 7007.
4c
4d
4e
55
0.022
0.040
0.047
OMe
42b
39b
NHMe
Cl
NHMe
CH2OH
OMe
(11) Pettit, G. R.; Singh, S. B.; Cragg, G. M. J. Org. Chem. 1985,
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37a
36
4f
0.398
5.51
10.3
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4431.
Cl
4g
4h
Cl
NHMe
38b
OMe
CH2NHC(O)(CH2)12Me
OMe
4i
42
64
0.462
0.489
CH2NHC(O)Me
OMe
4g
OMe
4k
4l
56
0.085
0.359
0.862
NHMe
NMe2
60b
56
4m
a Overall yield for (Z)-stilbene preparation including the stage of
TBS-group cleavage
b Overall yield for (Z)-stilbene preparation including the stage of Boc-
group cleavage
(21) Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6,
4215.
(22) Preparation of (Z)-3,4,5-Trimethoxy-β-Iodostyrene (2)
Into a flame-dried 2 L round-bottom flask equipped with a
magnetic stirrer and a septum was placed iodomethylene-
triphenylphosphonium iodide (62 g, 117 mmol).19,23 The
flask was then put under vacuum for 5 min and purged with
nitrogen. Dry THF (350 mL) was added, and the yellow
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Synlett 2012, 23, 1205–1208