126824-22-4Relevant academic research and scientific papers
Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: A facile access to substituted benzimidazole, bis-benzimidazole and imidazopyridine derivatives
Singh,Sasmal,Lu,Chatterjee
, p. 1380 - 1390 (2000)
A catalytic Fe(III)/Fe(II) redox cycling approach has been examined and applied towards synthesis of a wide range of benzimidazole, bis-benzimidazole and imidazopyridine derivatives from oxidative coupling of aromatic ortho-diamines with aromatic as well
Synthesis and investigation of novel benzimidazole derivatives as antifungal agents
Chandrika, Nishad Thamban,Shrestha, Sanjib K.,Ngo, Huy X.,Garneau-Tsodikova, Sylvie
, p. 3680 - 3686 (2016/07/20)
The rise and emergence of resistance to antifungal drugs by diverse pathogenic fungal strains have resulted in an increase in demand for new antifungal agents. Various heterocyclic scaffolds with different mechanisms of action against fungi have been investigated in the past. Herein, we report the synthesis and antifungal activities of 18 alkylated mono-, bis-, and trisbenzimidazole derivatives, their toxicities against mammalian cells, as well as their ability to induce reactive oxygen species (ROS) in yeast cells. Many of our bisbenzimidazole compounds exhibited moderate to excellent antifungal activities against all tested fungal strains, with MIC values ranging from 15.6 to 0.975?μg/mL. The fungal activity profiles of our bisbenzimidazoles were found to be dependent on alkyl chain length. Our most potent compounds were found to display equal or superior antifungal activity when compared to the currently used agents amphotericin B, fluconazole, itraconazole, posaconazole, and voriconazole against many of the strains tested.
Synthesis and biological evaluation of benzimidazole-oxindole conjugates as microtubule-targeting agents
Kamal, Ahmed,Nagaseshadri,Nayak, V. Lakshma,Srinivasulu, Vunnam,Sathish, Manda,Kapure, Jeevak Sopanrao,Suresh Reddy
, p. 72 - 84 (2015/10/20)
A series of benzimidazole-oxindole conjugates were synthesized and evaluated for their cytotoxic activity. The cytotoxicity assay results suggest that conjugates 5c and 5p exhibit promising cytotoxicity against human breast cancer cell line (MCF-7). The Cell cycle analysis revealed that these conjugates induced cell cycle arrest at G2/M phase in MCF-7 cells. The tubulin polymerization assay results suggested that these conjugates inhibit tubulin polymerization with IC50 values 1.12 and 1.59 μM respectively. Immunofluorescence analysis also suggested that these conjugates effectively inhibited the microtubule assembly in MCF-7 cells. Further, molecular docking studies indicated that these conjugates 5c and 5p interact and binds efficiently with the tubulin protein. By and large, the results demonstrated that these benzimidazole-oxindole conjugates possess cytotoxic property by inhibiting the tubulin polymerization.
Tris-benzimidazole derivatives: Design, synthesis and DNA sequence recognition
Ji, Yu-Hua,Bur, Daniel,H?sler, Walter,Schmitt, Valérie Runtz,Dorn, Arnulf,Bailly, Christian,Waring, Michael J.,Hochstrasser, Remo,Leupin, Werner
, p. 2905 - 2919 (2007/10/03)
Two tris-benzimidazole derivatives have been designed and synthesized based on the known structures of the bis-benzimidazole stain Hoechst 33258 complexed to short oligonucleotide duplexes derived from single crystal X-ray studies and from NMR. In both derivatives the phenol group has been replaced by a methoxy-phenyl substituent. Whereas one tris-benzimidazole carries a N-methyl-piperazine at the 6-position, the other one has this group replaced by a 2-amino-pyrrolidine ring. This latter substituent results in stronger DNA binding. The optimized synthesis of the drugs is described. The two tris-benzimidazoles exhibit high AT-base pair (bp) selectivity evident in footprinting experiments which show that five to six base pairs are protected by the tris-benzimidazoles as compared to four to five protected by the bis-benzimidazoles. The tris-benzimidazoles bind well to sequences like 5′-TAAAC, 5′-TTTAC and 5′-TTTAT, but it is also evident that they can bind weakly to sequences such as 5′-TATGTT-3′ where the continuity of an AT stretch is interrupted by a single G·C base pair.
Synthesis and evaluation of terbenzimidazoles as topoisomerase I inhibitors
Sun,Gatto,Yu,Liu,Liu,LaVoie
, p. 3638 - 3644 (2007/10/03)
The synthesis and pharmacological activity of a series of terbenzimidazoles are described. The ability of these derivatives to induce DNA cleavage in the presence of topoisomerase I was evaluated in vitro. These analogs were also assayed for their cytotoxicity in RPMI 8402 cells and the camptothecin-resistant CPT-K5 cells. In addition the potential for these compounds to serve as substrates for MDR1 was also determined. Several terbenzimidazoles exhibited similar cytotoxicity against variants of human tumor cells that either overexpress MDR1 or are camptothecin-resistant.
SYNTHESIS AND DNA BINDING PROPERTIES OF A PURINE ANALOGUE OF BISBENZIMIDE
Lee, Moses,Spotts, P. Hunter,Eckert, Jeffrey,Walker, Clint,Nobles, Jennifer A.
, p. 2093 - 2097 (2007/10/02)
The synthesis of a purine containing analogue (1) of bisbenzimide (2) and its DNA binding properties are described.Analogue 1 is found to have increased tolerance for binding to GC sites implying the formation of the new hydrogen bonds between guanine-2-N
