Figures & data
Figure 1. Benzimidazole structures I–XIV substituted at position 1 as lead potent active compounds for antitumor and antiviral activity.
Figure 2. Structural requirements around benzimidazole nucleus for the study.
Scheme 1. Synthesis of novel benzimidazole derivative 3–10 connected at position 1 via methylene linker.
Scheme 2. Synthesis of benzimidazole derivatives 11–13 with heterocyclic rings connected at position 1 via methylene linker (using different diols).
Figure 3. X-ray structure of 2-(2-methyl-5-nitro-1H-benzo[d]imidazol-1-yl)-1-phenyl-3-p-tolylprop-2-en-1-one; 15a(Z).
![Figure 3. X-ray structure of 2-(2-methyl-5-nitro-1H-benzo[d]imidazol-1-yl)-1-phenyl-3-p-tolylprop-2-en-1-one; 15a(Z).](/cms/asset/648ecf7b-28bc-4005-914f-ac7c5510c789/ienz_a_979344_f0003_b.jpg)
Scheme 3. Synthesis of benzimidazole derivatives 14–30 with heterocyclic rings directly connected at position 1.
Table 1. % Growth inhibitory activity at 300 µM of the synthesized compounds, indicating IC50 (µg/ml) between brackets.
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Figure 4. In vivo assay of acute toxicity LD50 of the synthesized compound 9 µg/kg body weight.
Table 2. Liver function test of normal, DENA- and compound 9-treated DENA rats.
Figure 5. Liver section of untreated normal control rats [A] showed unremarkable pathological changes. Liver section from rats treated with DENA showed: hyperchromatism, hyperplasia, proliferating hepatocytes [B]; loss architecture, both hepatic and portal with significant tumor thrombi within portal vessels, slightly larger tumor cells having more irregular nuclei [C]; malignant nuclei [D]; megalocytosis, hyperchromatic nuclei, nuclear vacuolization and prominence [E]; dissolution of hepatic cords appeared as empty vacuoles aligned by strands of necrotic hepatocytes [F]; disarrangement of normal hepatic cells with intense centrilobular necrosis [G]. Liver of the DENA-rats treated with compound 9 showed normal hepatic lobule architecture [H] (H&E, magnification 400×).
![Figure 5. Liver section of untreated normal control rats [A] showed unremarkable pathological changes. Liver section from rats treated with DENA showed: hyperchromatism, hyperplasia, proliferating hepatocytes [B]; loss architecture, both hepatic and portal with significant tumor thrombi within portal vessels, slightly larger tumor cells having more irregular nuclei [C]; malignant nuclei [D]; megalocytosis, hyperchromatic nuclei, nuclear vacuolization and prominence [E]; dissolution of hepatic cords appeared as empty vacuoles aligned by strands of necrotic hepatocytes [F]; disarrangement of normal hepatic cells with intense centrilobular necrosis [G]. Liver of the DENA-rats treated with compound 9 showed normal hepatic lobule architecture [H] (H&E, magnification 400×).](/cms/asset/b854eb39-21cf-4eeb-91e6-d02032e58d6d/ienz_a_979344_f0005_b.jpg)