Synthesis, antitumor screening and cell cycle analysis of novel benzothieno[3,2-b]pyran derivatives

Figures & data

Figure 1. Design of the target compounds 2a–f and 3a–f.

Figure 2. GI₅₀ of compound 3e in μM against leukemia, non-small cell lung cancer, colon cancer and CNS cancer cell lines.

Figure 3. GI₅₀ of compound 3e in μM against melanoma, ovarian cancer, renal cancer, prostate cancer and breast cancer cell lines.

Table 1. Results of in vitro anticancer screening of compounds 2–4.

			Total MG-MID^a^,^b(μM)
Compound No.	Ar	Mean growth (%)	GI50	TGI	LC50
2a	4-BrC6H4	95.73	n.t	n.t	n.t
2b	4-ClC6H4	91.82	n.t	n.t	n.t
2c	4-FC6H4	79.57	n.t	n.t	n.t
2d	4-CH3OC6H4	88.62	n.t	n.t	n.t
2f	2-Pyridyl	93.14	n.t	n.t	n.t
3a	4-BrC6H4	20.25	0.76	6.02	32.36
3b	4-ClC6H4	15.92	0.67	5.24	33.11
3c	4-FC6H4	22.64	0.50	14.79	72.44
3d	4-CH3OC6H4	26.03	2.45	13.18	57.54
3e	4-NO2C6H4	17.13	0.11	7.94	42.66
3f	2-Pyridyl	36.88	n.t	n.t	n.t
4a	4-BrC6H4	89.26	n.t	n.t	n.t
4b	4-ClC6H4	91.28	n.t	n.t	n.t
4c	4-FC6H4	90.86	n.t	n.t	n.t
4d	4-CH3OC6H4	85.09	n.t	n.t	n.t

^aMG-MID is the calculated mean full panel or individual subpanel GI₅₀, TGI, or LC₅₀.

^b n.t: not tested.

Figure 4. (a) Effect of compound 3e on DNA-ploidy flow cytometric analysis of HCT-116 cells after 24 h and 48 h. (b) Bar chart showing percentage of HCT-116 cells at each phase of the cell cycle in control cells and cells treated with compound 3e after 24 h and 48 h.

Figure 5. Effects of compound 3e on apoptosis of HCT-116 cells after 24 h and 48 h. The data were presented as means ± standard error of the mean for three independent replicates.

Scheme 1. Synthesis of the target compounds 2a–f, 3a–f and 4a–e.