747356-47-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 33402-67-4 sodium hydroxy(4-methoxyphenyl)methanesulfonate 
• 619-05-6 3,4-diaminobenzoic acid 
• 174422-17-4 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid 

Downstream Products

• 1289633-10-8 C₃₀H₃₃N₉O₄ 
• 1289633-07-3 C₃₂H₃₆N₈O₄ 
• 1289633-08-4 C₃₁H₃₅N₉O₄ 

Relevant academic research and scientific papers

Hx, a novel fluorescent, minor groove and sequence specific recognition element: Design, synthesis, and DNA binding properties of p - anisylbenzimidazole-imidazole/pyrrole-containing polyamides

With the aim of incorporating a recognition element that acts as a fluorescent probe upon binding to DNA, three novel pyrrole (P) and imidazole (I)-containing polyamides were synthesized. The compounds contain a p-anisylbenzimidazolecarboxamido (Hx) moiety attached to a PP, IP, or PI unit, giving compounds HxPP (2), HxIP (3), and HxPI (4), respectively. These fluorescent hybrids were tested against their complementary nonfluorescent, non-formamido tetraamide counterparts, namely, PPPP (5), PPIP (6), and PPPI (7) (cognate sequences 5′-AAATTT-3′, 5′-ATCGAT-3′, and 5′-ACATGT-3′, respectively). The binding affinities for both series of polyamides for their cognate and noncognate sequences were ascertained by surface plasmon resonance (SPR) studies, which revealed that the Hx-containing polyamides gave binding constants in the 106 M-1 range while little binding was observed for the noncognates. The binding data were further compared to the corresponding and previously reported formamido-triamides f-PPP (8), f-PIP (9), and f-PPI (10). DNase I footprinting studies provided additional evidence that the Hx moiety behaved similarly to two consecutive pyrroles (PP found in 5-7), which also behaved like a formamido-pyrrole (f-P) unit found in distamycin and many formamido-triamides, including 8-10. The biophysical characterization of polyamides 2-7 on their binding to the abovementioned DNA sequences was determined using thermal melts (δTM), circular dichroism (CD), and isothermal titration calorimetry (ITC) studies. Density functional calculations (B3LYP) provided a theoretical framework that explains the similarity between PP and Hx on the basis of molecular electrostatic surfaces and dipole moments. Furthermore, emission studies on polyamides 2 and 3 showed that upon excitation at 322 nm binding to their respective cognate sequences resulted in an increase in fluorescence at 370 nm. These low molecular weight polyamides show promise for use as probes for monitoring DNA recognition processes in cells.

Novel clarithromycin analogs with C-4′′ 2-arylbenzimidazolyl bishydrazide side chain: Synthesis and antibacterial evaluation

A series of novel 4′′-O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4′′-O-2- arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4′′ bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.

Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

Novel 4″-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4″ bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the mef gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4″-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4″-O-(2-alkyl)benzimidazolyl derivatives.

Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity

A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were

SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLE-5(6)-CARBOXAMIDES AND EVALUATION OF THEIR ANTIMICROBIAL ACTIVITY

A series of 14,N'-(N,N-dialkylaminoethyl)-benzimidazole-5(6) or 5-carboxamides (1-14), having several substituents on the azole and benzene nuclei, were prepared and evalueted in vitro for antimicrobial activity.The precursor bezimidazolecarboxylic acids (15-27) were prepared via oxidative condensation of diaminobenzoic acids and several aldehydes with cupric ion.Compounds 11-14 were prepared by selective regioisomer synthesis.All carboxamides were prepared from the corresponding acids and N,N-dialkylethylenediamine.Antibacterial and antifungal activities were determined as MICs values.Of the synthesized compounds 1-10, 6 and 10 were found to be most favourable.In order to clarify the effect of the substituents at N1 on antimicrobial activity, 12 was prepared by p-chlorobenzyl substitution of compound 6, and increased activity was shown.Compounds 13 and 14, which were prepared by replacement with more bulky alkyl groups on the tert-N atom than 12, gave the best results.