54998-08-2

Usage

Chemical Properties

Solid

InChI:InChI=1/C11H18N4/c1-14-4-6-15(7-5-14)9-2-3-10(12)11(13)8-9/h2-3,8H,4-7,12-13H2,1H3

Upstream product

• 364-53-4 4-fluoro-1,2-dinitro-benzene 
• 109-01-3 1-methyl-piperazine 
• 1635-61-6 5-chloro-2-nitroaniline 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 23491-48-7 5-(4-methylpiperazine-1-yl)-2-nitroaniline 

Downstream Products

• 129011-97-8 4-[5-(4-Methyl-piperazin-1-yl)-1H-benzoimidazol-2-yl]-benzonitrile 
• 129012-02-8 2-(4-Methoxy-phenyl)-6-[6-(4-methyl-piperazin-1-yl)-1H-benzoimidazol-2-yl]-benzooxazole 
• 120423-35-0 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5⁽⁶⁾-(4-methyl-1-piperazinyl)benzimidazole 
• 129244-58-2 2-(3,5-di-tert-butyl-4-hydroxybenzyl)-5⁽⁶⁾-(4-methyl-1-piperazinyl)benzimidazole 
• 129244-61-7 2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5⁽⁶⁾-(4-methyl-1-piperazinyl)benzimidazole 
• 129244-66-2 2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5'(6')-benzimidazolyl>-5(6)-<1-(4-methylpiperazinyl)>benzimidazole 
• 129244-67-3 2-<2-(3,5-di-tert-butyl-4-hydroxybenzyl)-5'(6')-benzimidazolyl>-5(6)-<1-(4-methylpiperazinyl)>benzimidazole 
• 129244-68-4 2-<2-(3,5-di-tert-butyl-4-hydroxyphenethyl)-5'(6')-benzimidazolyl>-5(6)-<1-(4-methylpiperazinyl)>benzimidazole 
• 23623-05-4 4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>-2-nitroaniline 
• 23555-00-2 4-dimethylamino-1-<5'-<5''-(4'''-methylpiperazin-1'''-yl)benzimidazol-2''-yl>benzimidazol-2'-yl>benzene 
• 23623-08-7 2'-phenyl-5-(4-methylpiperazinyl)-2,5'-bi-1H-benzimidazole 
• 23491-54-5 2'-m-tolyl-5-(4-methylpiperazinyl)-2,5'-bi-1H-benzimidazole 
• 23554-98-5 2'-(4-hydroxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole 
• 23491-55-6 2'-(naphth-2-yl)-5-(4-methylpiperazinyl)-2,5'-bi-1H-benzimidazole 

Relevant academic research and scientific papers

Kinetic Target-Guided Synthesis of Small-Molecule G-Quadruplex Stabilizers

The formation of a G-quadruplex motif in the promoter region of the c-MYC protooncogene prevents its expression. Accordingly, G-quadruplex stabilization by a suitable ligand may be a viable approach for anticancer therapy. In our study, we used the 4-(4-m

DNA sequence-specific ligands: XV. Synthesis and spectral characteristics of a new series of dimeric bisbenzimidazoles DB(1, 2, 6, 8, 9, 10, 12)

Seven fluorescent symmetric dimeric bisbenzimidazoles DB(n) capable of occupying up to one turn of the double-stranded B-form DNA have been designed and synthesized with the aim to develop DNAdependent enzyme inhibitors. The DB(n) compounds contain four 2

Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy

As epigenetic readers, bromodomain and extra-terminal domain (BET) family proteins bind to acetylated-lysine residues in histones and recruit protein complexes to promote transcription initiation and elongation. Inhibition of BET bromodomains by small molecule inhibitors has emerged as a promising therapeutic strategy for cancer. Herein, we describe our efforts toward the discovery of a novel series of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as BET inhibitors. Intensive structural modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic properties and antitumor efficacy in MV4-11 mouse xenograft model with acceptable tolerability. These results indicated that BET inhibitors could be potentially used to treat hematologic malignancies and some solid tumors.

Di-(benzimidazole)-1, 2, 3-triazole derivative as well as preparation and application thereof in inflammatory dermatosis

The invention belongs to the technical field of drug small molecules, and particularly discloses a brand-new di-(benzimidazole)-1, 2, 3-triazole derivative as well as preparation and application of the brand-new di-(benzimidazole)-1, 2, 3-triazole derivative. The research finds that the brand new compound has an excellent drug effect and low toxic and side effects on the aspect of inflammatory dermatosis, and has a good application prospect in the aspect of drug development of the inflammatory dermatosis.

Benzimidazole compound, preparation method thereof and application of the benzimidazole compound in preparation of ferroptosis inhibitor

The invention discloses a benzimidazole compound, a preparation method thereof and application of the benzimidazole compound in preparation of a ferroptosis inhibitor. The benzimidazole compound has a structure as shown in a formula (I) or a formula (II)

Pyrrole derivative as well as preparation method and application thereof

The invention belongs to the field of medical chemistry, and relates to a pyrrole derivativex as well as a preparation method and application thereof. A compound with a structure shown as a general formula (I), or one or a mixture of more of a tautomer, a

Method for synthesizing dovitnib intermediate in microchannel reactor

The invention discloses a method for synthesizing a dovitnib intermediate in a microchannel reactor and belongs to the technical field of antitumor drug synthesis in organic synthesis. The method comprises adding 5-(4-methylpiperazine)-2-nitroaniline into

Selective Inhibition of Escherichia coli RNA and DNA Topoisomerase i by Hoechst 33258 Derived Mono-and Bisbenzimidazoles

A series of Hoechst 33258 based mono-and bisbenzimidazoles have been synthesized and their Escherichia coli DNA topoisomerase I inhibition, binding to B-DNA duplex, and antibacterial activity has been evaluated. Bisbenzimidazoles with alkynyl side chains display excellent E. coli DNA topoisomerase I inhibition properties with IC50 values 32 μg/mL). Bisbenzimidazoles showed varied stabilization of B-DNA duplex (1.2?ê'23.4 °C), and cytotoxicity studies show similar variation dependent upon the side chain length. Modeling studies suggest critical interactions between the inhibitor side chain and amino acids of the active site of DNA topoisomerase I.

Synthesis and investigation of novel benzimidazole derivatives as antifungal agents

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.

New dimeric carbazole-benzimidazole mixed ligands for the stabilization of human telomeric G-quadruplex DNA and as telomerase inhibitors. A remarkable influence of the spacer

The development of G-quadruplex (G4) DNA binding small molecules has become an important strategy for selectively targeting cancer cells. Herein, we report the design and evolution of a new kind of carbazole-based benzimidazole dimers for their efficient telomerase inhibition activity. Spectroscopic titrations reveal the ligands high affinity toward the G4 DNA with significantly higher selectivity over duplex-DNA. The electrophoretic mobility shift assay shows that the ligands efficiently promote the formation of G4 DNA even at a lower concentration of the stabilizing K+ ions. The TRAP-LIG assay demonstrates the ligand's potential telomerase inhibition activity and also establishes that the activity proceeds via G4 DNA stabilization. An efficient nuclear internalization of the ligands in several common cancer cells (HeLa, HT1080, and A549) also enabled differentiation between normal HFF cells in co-cultures of cancer and normal ones. The ligands induce significant apoptotic response and antiproliferative activity toward cancer cells selectively when compared to the normal cells.