Synthesis and evaluation of naphthalene-based thiosemicarbazone derivatives as new anticancer agents against LNCaP prostate cancer cells

Figures & data

Scheme 1. The synthetic route for the preparation of the thiosemicarbazone derivatives (1–14). Reagents and conditions: (i) NH₂NH₂·H₂O, ethanol, r.t., 4 h; (ii) ArCOCH₃, ethanol, reflux, 8 h.

Table 1. Some properties of the thiosemicarbazone derivatives (1–14).

Compound	R	Yield (%)	M.p. (°C)	Molecular formula	Molecular weight
1	H	81	163–164	C19H17N3S	319.42
2	F	83	185–186	C19H16FN3S	337.41
3	Cl	85	144–145	C19H16ClN3S	353.87
4	Br	88	206–207	C19H16BrN3S	398.32
5	NO2	90	201–202	C19H16N4O2S	364.42
6	OH	77	215–216	C19H17N3OS	335.42
7	OCH3	76	170–171	C20H19N3OS	349.45
8	CH3	79	180–182	C20H19N3S	333.45
9	CF3	80	211–213	C20H16F3N3S	387.42
10	SO2CH3	79	220–221	C20H19N3O2S2	397.51
11	CN	91	213–215	C20H16N4S	344.43
12	OCF3	75	216–217	C20H16F3N3OS	403.42
13	4-Morpholinyl	84	205–206	C23H24N4OS	404.53
14	1-Piperidinyl	81	188–190	C24H26N4S	402.56

Figure 1. Reducing effect of compound 6 on the number of living LNCaP cells. *p < 0.05, ***p < 0.001.

Figure 2. Compound 8 diminished cell viability only after exposure with 75 µM. ***p < 0.001.

Figure 3. MTT analysis results of LNCaP treated with different concentrations of compound 11. Cell viability inhibiting effect was found with only 75 µM. ***p < 0.001.

Figure 4. Images of LNCaP cells under microscope treated with compound 6.

Figure 5. Flow cytometric analysis of LNCaP cells treated with compound 6.

Table 2. Apoptotic percentages of the control and drug groups (n = 3).

Cell percentage	Control	50 µM Compound 6	75 µM Compound 6
Alive	96 ± 2.4	89 ± 1.8	82 ± 1.6
Early apoptotic	0.1 ± 0.01	2.9 ± 1.1	9.3 ± 2.1
Late apoptotic or necrotic	2.6 ± 1.2	6.6 ± 1.5	7.9 ± 1.8