155221-51-5Relevant articles and documents
Synthesis and antinociceptive activity of meperidine-like benzimidazole derivatives
Ercanli, Taner,Bal, Nur Banu,?zdemir, Elif Derya,Dündar, Yasemin,Uluda?, M. Orhan,?akir, Bilge,?zden, Tuncel,?nkol, Tijen
, p. 15 - 22 (2016/07/15)
(Graph presented) A series of novel benzimidazole derivatives have been prepared and characterized by IR, 1H-NMR spectroscopic data and elemental analysis. All the final compounds were screened for their antinociceptive activities with tail flick test. Among the synthesized compounds 3a, 4a, 4c, 8a, 9a exhibited significant antinociceptive activity. Compound 9a was found to have the highest antinociceptive activity at both 60 minutes and 120 minutes. Additionally, compounds 3a, 4a, 8a and 9a showed naloxone-reversible antinociceptive activity.
New (E)-1-alkyl-1H-benzo[d]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies
Sharma, Pankaj,Thummuri, Dinesh,Reddy, T. Srinivasa,Senwar, Kishna Ram,Naidu,Srinivasulu, Gannoju,Bharghava, Suresh K.,Shankaraiah, Nagula
, p. 584 - 600 (2016/07/22)
A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 8l showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50values of 3.26 ± 0.24 μM and 5.96 ± 0.67 μM respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 8l led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 8l induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 8l treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells.
Structure-Activity Studies of Benzimidazole-Based DNA-Cleaving Agents. Comparison of Benzimidazole, Pyrrolobenzimidazole, and Tetrahydropyridobenzimidazole Analogues
Skibo, Edward B.,Islam, Imadul,Heileman, Matthew J.,Schulz, William G.
, p. 78 - 92 (2007/10/02)
The synthesis and cytotoxic properties of benzimidazole-based DNA-cleaving agents are presented herein.These agents include pyrrolobenzimidazole (PBI), benzimidazole (BI), and tetrahydropyridobenzimidazole (TPBI) analogues.As a result of these studies, it is concluded that the pyrrolo ring is not necessary for cytotoxicity (PBI is only slightly more cytotoxic than BI) but that homologation of the pyrrolo ring by one carbon results in a system, TPBI, prone to decomposition.Another conclusion is that the 6-aziridinyl derivative of the PBI system is more potent than the 7-aziridinyl derivative.Comparative studies with known antitumor agents revealed that the benzimidazole-based DNA-cleaving agents possess a unique spectrum of activity.Noteworthy observations are the high level of cytotoxicity against melanoma cell lines and the complete absence of activity against leukemia cell lines.The reductive activation and DNA-cleavage properties of the most active analogue (BI-A) are also presented.Reduction of the quinone ring to the hydroquinone results in nucleophile and proton trapping by the aziridinyl group.Documented nucleophiles include water and the oxygen anion of 5'-dAMP.In addition, reduced BI-A reacts with DNA to form a stable adduct, which cleaves at G + A bases upon heating in basic gel-loading solution.
