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. Author manuscript; available in PMC: 2008 Jan 1.
Published in final edited form as: Bioorg Med Chem. 2006 Oct 10;15(1):495–510. doi: 10.1016/j.bmc.2006.09.039

Table 3.

In Vitro Differential Cytotoxicity of Lavendamycins

graphic file with name nihms14804t3.jpg
LC50 (μ M)a
Cell Linesb
No. R1 R2 R3 R4 NRKE K/1 H/1.2 N/4.2 3LL
19 CH3CO CO2CH2CH3 H H 0.30 0.04 0.36 0.20 3.2
20 CH3CO CO2CH(CH2)5 H H 0.70 0.40 0.69 0.70 1.0
21 CH3CO CO2C5H11-i CH3 H 4.16 5.0 4.3 3.89 7.4
22 CH3CO CO2CH2CH2N(CH3)2 H H 0.37 0.14 0.24 0.29 0.50
23 CH3CO CO2CH2CH2N(CH3)2 CH3 H 0.09 0.06 0.09 0.09 0.48
24 CH3CO CO2C4H9-n H OCH3 2.5 2.2 2.1 2.2 >3.3
25 CH3CO CO2C4H9-n H F 0.62 0.33 0.70 0.84 2.1
26 ClCH2CO CO2CH3 CH3 H 0.58 0.79 0.58 0.70 2.0
27 ClCH2CO CO2C4H9-n H H 0.96 0.52 0.74 1.05 2.3
28 ClCH2CO CO2C8H17-n H H >33 15.0 >33 >33 >33
29 n-C3H7CO CO2CH3 H H 0.70 0.50 0.66 0.64 1.3
30 n-C3H7CO CO2CH3 CH3 H 0.32 0.33 0.40 0.42 0.82
31 n-C3H7CO CO2C5H11-I H H 1.00 0.60 0.37 0.65 2.4
32 n-C3H7CO CO2C8H17-n H H >33 3.3 16.0 15.0 16.0
33 i-C3H7CO CO2CH3 H H 0.70 0.50 0.66 0.64 1.3
34 i-C3H7CO CO2C4H9-n H H 0.90 0.40 0.61 0.50 0.90
35 H H H H 0.10 0.031 0.11 0.06 0.25
36 CH3CO H H H 0.40 0.44 0.40 0.49 3.0
37 CH3CO CH2OH H H 0.25 0.20 0.20 0.22 0.44
38 CH3CO CO2H H H 0.15 0.07 0.11 0.10 0.40
39 CH3CO CONH2 H H 0.90 0.35 0.23 0.22 0.21
40 CH3CO CO2CH3 H H 0.50 0.11 0.51 0.52 0.84
41 CH3CO CO2C5H11-I H H 1.62 0.09 1.42 1.5 1.69
42 CH3CO CO2C8H17-n H H >33 0.25 7.6 9.0 >33
43 CH3CO CO2CH2Ph H H 9.5 9.5 >10 >33 >33
44 CH3CO CO2CH3 CH3 H 0.90 0.10 0.70 NT >33
45 ClCH2CO CO2C5H11-I H H 1.35 0.56 1.32 1.2 3.2
46 n-C3H7CO CO2C4H9-n H H 0.66 0.50 0.40 0.70 2.3
a

LC50 is the concentration of analogue that afforded 50% reduction in colony number after a 5-day incubation.With two exceptions, the reported values are derived from representative experiments performed in triplicate and interpolated from at least eight different concentrations of drug ranging from 0.01 to 33 μM. Those values reported as 3.3 or > 3.3 were determined in screening assays where only two concentrations of drug were used, i.e., 3.3 and 33 μM. All experiments were performed at least twice. NT = Not tested.

b

Cell lines: See Table 2 footnotes. For the syntheses of 35 and 44, see references 36, 37; for 38, 39, 42, 43, 40, 45, 46 see reference 40 and for 36, 37, 40, 41 see reference 42.