Figures & data
Figure 2. Binding sites A and B and designation of the torsion angles θ1 and θ2 of the compounds synthesized.
![Figure 2. Binding sites A and B and designation of the torsion angles θ1 and θ2 of the compounds synthesized.](/cms/asset/014109b7-b910-4744-93d3-3e8641b3d218/ienz_a_1043296_f0002_c.jpg)
Scheme 1 Synthetic chemical pathway of compounds in series 1–3. The reagents used in the syntheses were as follows: (I) 2-bromo-4,5-dimethoxy-benzaldehyde/CH3COOH/dry HCl; (II) 4-dimethylamino-benzaldehyde/CH3COOH/dry HCl; (III) 4-trifluoromethyl-benzaldehyde/CH3COOH/dry HCl; (IV) 4-nitrobenzoyl chloride/NaOH/ClCH2CH2Cl/K2CO3/tetrabutylammonium bromide or 4-methylbenzene sulfonyl chloride/4-acetamidobenzenesulfonyl chloride/4-nitrobenzenesulfonyl/NaOH/ClCH2CH2Cl/tetrabutylammonium bromide/CH3COOH.
![Scheme 1 Synthetic chemical pathway of compounds in series 1–3. The reagents used in the syntheses were as follows: (I) 2-bromo-4,5-dimethoxy-benzaldehyde/CH3COOH/dry HCl; (II) 4-dimethylamino-benzaldehyde/CH3COOH/dry HCl; (III) 4-trifluoromethyl-benzaldehyde/CH3COOH/dry HCl; (IV) 4-nitrobenzoyl chloride/NaOH/ClCH2CH2Cl/K2CO3/tetrabutylammonium bromide or 4-methylbenzene sulfonyl chloride/4-acetamidobenzenesulfonyl chloride/4-nitrobenzenesulfonyl/NaOH/ClCH2CH2Cl/tetrabutylammonium bromide/CH3COOH.](/cms/asset/392014f5-1b87-4799-81c2-aa6d29220bb4/ienz_a_1043296_sch0001_b.jpg)
Table 1. Cytotoxicity of 1a–1e, 2a–2e and 3a–3e against human SK-BR-3, PG-BE1, NCI-H460, MIA PaCa-2 and SW1990 cell lines.
Figure 3. The inhibitory effect of compounds 1a–1e and 3a–3e against five human carcinoma cell lines.
![Figure 3. The inhibitory effect of compounds 1a–1e and 3a–3e against five human carcinoma cell lines.](/cms/asset/01f65e9d-5e94-4749-a064-38ec59d5034b/ienz_a_1043296_f0003_b.jpg)
Figure 4. The ORTEP figure of 1e (displacement ellipsoids with 30% probability, omitting two molecules of CHCl3).
![Figure 4. The ORTEP figure of 1e (displacement ellipsoids with 30% probability, omitting two molecules of CHCl3).](/cms/asset/43638b7f-914d-438f-846b-53c69b6332ce/ienz_a_1043296_f0004_b.jpg)