Novel symmetric bis-benzimidazoles: Synthesis, DNA/RNA binding and antitrypanosomal activity

Bistrović, Andrea; Stolić, Ivana; Krstulović, Luka; Taylor, Martin C.; Kelly, John M.; Tomić, Sanja; Tumir, Lidija-Marija; Bajić, Miroslav; Raić‐Malić, Silvana

doi:10.1016/j.ejmech.2019.04.007

Cited by 15 publications

(15 citation statements)

References 53 publications

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“…Necessary reagents for the synthesis of the targeted heterocyclic compounds (1)(2)(3)(4) NMR and IR were used for characterize the structures of the compounds obtained. In Erciyes University Central Research Laboratory, both 1 H NMR and 13 C NMR spectra were taken with Bruker Ultra Shield 400 MHz NMR Spectroscopy using CDCl3 or DMSO-d6 solvents.…”

Section: Reagentsmentioning

confidence: 99%

“…Compounds containing benzimidazole nucleus demonstrate a wide variety of biological activity properties such as anticancer, antitubercular antimicrobial, antifungal, antioxidant, antidiabetic and etc [1][2][3][4][5][6][7][8][9][10][11][12][13]. On the other hand, heterocyclic benzimidazole derivatives have different application area and can be used as catalysts [14][15][16] and sensors [17,18].…”

Section: Introductionmentioning

confidence: 99%

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Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Akkoç

2019

Cumhuriyet Science Journal

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Four different benzimidazolium salts (1-4) were prepared in three steps at 80 o C and their structures were elucidated using spectroscopic methods. The compounds (1-4) obtained were tested in in situ medium as catalyst in the carbon-carbon (C-C) bond formation reactions of two different boronic acid derivatives with various aryl halides in the presence of palladium acetate (PdOAc)2 and sodium tertiarybutoxide (NaOBu t) as a base. With this reaction, four coupling products (5-8) were synthesized in different yields ranging from 11 to 93%. Compound 2 from the carbene precursors tested in the Suzuki-Miyaura cross-coupling reaction was found to be a more effective catalyst candidate than others.

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Section: Reagentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Akkoç

2019

Cumhuriyet Science Journal

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“…Benzimidazoles treat mitochondrial dysfunction in Alzheimer disease [45], possess neurotropic, psychoactive, analgesic effects [46], anticoagulant proprieties [47] and are efficient agents in diabetes mellitus [48]. Benzimidazole derivatives were reported as potential EGFR and erbB2 inhibitors [49,50], DNA/RNA binding ligands [51,52] and antiquorum-sensing agents [53].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

et al. 2020

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The tri-component synthesis of novel chiral benzimidazole Mannich bases, by reaction between benzimidazole, aqueous 30% formaldehyde and an amine, the biological evaluation and DFT studies of the new compounds are reported here. The 1 H-NMR, 13 C-NMR, FTIR spectra and elemental analysis confirm the structures of the new compounds. All synthesized compounds were screened by qualitative and quantitative methods for their in vitro antibacterial activity against 4 bacterial strains. DFT studies were accomplished using GAMESS 2012 software and HOMO-LUMO analysis allowed the calculation of electronic and structural parameters of the chiral Mannich bases. The geometry of 1-methylpiperazine, the cumulated Mullikan atomic charges of the two heteroatoms and of the methyl, and the value of the global electrophilicity index (ω = 0.0527) of the M-1 molecule is correlated with its good antimicrobial activity. It was found that the presence of saturated heterocycles from the amine molecule, 1-methyl piperazine and morpholine, respectively, contributes to an increased biological activity, compared to aromatic amino analogs, diphenylamino-, 4-nitroamino-and 4-aminobenzoic acid. The planarity of the molecules, specific bond lengths and localization of HOMO-LUMO orbitals is responsible for the best biological activities of the compounds.

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“…Examples of bioactive triazole-linked dimeric heterocycles include anticancer agent 1 [5][6][7][8], antimicrobial 2 [9][10][11][12], as well as antioxidants [10] and antipsychotic agents [13] (Figure 1). It is important to note that these compounds have an aliphatic chain spacer between the 1,2,3-triazole rings, probably for lipophilic control, and a heterocyclic component linked to the triazole ring.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy

2020

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Novel symmetric bis-benzimidazoles: Synthesis, DNA/RNA binding and antitrypanosomal activity

Cited by 15 publications

References 53 publications

Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy

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