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. 2021 Nov 8;11(57):36023–36033. doi: 10.1039/d1ra07173d

Cytotoxicity of kobusine (9) and pseudokobusine (105) and their acylated derivatives (IC50, μM).

graphic file with name d1ra07173d-u1.jpg
R1–R3 A549 DU145 KB KB-VIN KB/KB-VIN ratio
R2 = R3 = OH (9) >40 >40 >40 >40
R2 = R3 = OBz (9a) 8.4 9.3 6.0 7.5 0.80
R2 = R3 = OAs (9b) 6.7 7.1 5.3 5.2 1.02
R2 = ONB, R3 = OH (9c) 19.5 15.3 13.9 17.9 0.78
R2 = R3 = ONB (9d) 6.9 7.0 5.3 5.5 0.96
R2 = OPFMB, R3 = OH (9e) 17.2 13.2 12.7 14.1 0.90
R2 = OFMTB, R3 = OH (9f) 14.1 9.6 11.7 10.9 1.07
R2 = R3 = OFB (9g) 8.1 6.8 5.2 7.1 0.73
R2 = R3 = OFMCM (9h) 5.5 6.2 4.1 3.1 1.32
R1 = R2 = R3 = OH (105) >40 >40 >40 >40
R1 = R2 = OBz, R3 = OH (105a) 19.3 15.3 12.8 10.2 1.25
R1 = OH, R2 = R3 = OBz (105b) 8.8 7.6 5.2 6.3 0.83
R1 = R3 = OH, R2 = OAs (105c) 15.4 13.2 11.1 15.7 0.70
R1 = R3 = OH, R2 = OVr (105d) 8.0 15.3 14.9 20.1 0.74
R1 = R2 = OVr, R3 = OH (105e) 16.0 16.9 19.7 14.7 1.34
R1 = R3 = OVr, R2 = OH (105f) 15.2 16.6 18.1 12.2 1.48
R1 = R2 = OH, R3 = ONB (105g) 5.8 7.2 6.4 6.4 1.00
R1 = OH, R2 = R3 = OMNB (105h) 5.0 5.2 5.6 5.6 1.00
R1 = R3 = OH, R2 = OMFMB (105i) 6.8 7.7 8.9 6.2 1.44
R1 = R3 = OH, R2 = OFMTB (105j) 17.9 14.5 15.7 13.9 1.13
R1 = R3 = OH, R2 = OCn (105k) 8.4 6.5 7.0 6.4 1.09
R1 = R3 = OH, R2 = OTr (105l) 6.4 6.0 6.6 5.2 1.27
Paclitaxel (nM) 4.8 5.9 5.8 2405.4 0.0067