Cytotoxic activities of some benzothiazole-piperazine derivatives

Figures & data

Figure 1. Synthesis of compounds 1a–f and 2a–d.

Table 1. Structural and physical properties of compounds 1a–f and 2a–d.

Compounds	R1	R2	M.P. (°C)	Yield %	Log P*
1a	Methyl	2-Methoxyphenyl	121.9†	48	4.15
1b	Methyl	2-Methoxyethyl	81.1	12	2.04
1c	Methyl	Cyclohexyl	181.3	18	3.74
1d	Methyl	4-Pyridyl	100.8	22	2.94
1e	Methyl	3,4-Dichlorophenyl	243.8	16	5.39
1f	Methyl	4-Chlorobenzyl	189.6	12	4.49
2a	Ethoxy	4-Methylphenyl	146.7	36.5	4.76
2b	Ethoxy	2-Chlorophenyl	>300	47.5	4.83
2c	Ethoxy	4-Cyanophenyl	>300	42.7	4.31
2d	Ethoxy	2-Cyanophenyl	>300	25.6	4.31

*Log P were calculated using ChemDraw Ultra V.9.0 (ChembridgeSoft Corp., Cambridge, MA).

†Melting point of compound 1a in the original reference15 is reported as 122–124 °C.

Table 2. Cytotoxic activity data for compounds 1a–f and 2a–d.

			Cancer cell line (GI50, µM)
Compounds	HCT-116	R^2	MCF-7	R^2	HUH-7	R^2
1a	4.8	1.0	15.1	1.0	5.7	1.0
1b	7.7	0.8	no inh	–	10.7	0.8
1c	15.1	0.9	26.9	0.8	7.9	0.9
1d	7.9	0.9	9.2	0.9	3.1	0.9
1e	8.0	0.9	16.6	0.9	9.7	1.0
1f	5.0	0.8	no inh	–	7.0	0.9
2a	4.5	1.0	61.4	0.9	9.4	1.0
2b	5.8	0.9	20.4	0.9	6.5	0.9
2c	6.3	0.8	29.8	0.9	7.4	0.8
2d	25.3	0.9	19.8	0.9	6.7	0.9
5-FU	30.66		3.51		18.67

Figure 2. Fluorescence images of liver cancer (HUH7) cells^a,b. ^aCells were placed on cover slips and treated with GI₅₀ concentration of compound 1d or DMSO control for 72 h. ^bNuclear Hoechst 33258 stain was used to stain the cells.

Figure 3. Cell cycle distribution analysis of compound 1d.

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