- Bisbenzimidazole Derivatives as Potential Antimicrobial Agents: Design, Synthesis, Biological Evaluation and Pharmacophore Analysis
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In an attempt to design and synthesize a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various aliphatic and heteroaliphatic dicarboxylic acids to generate a small library of 26 head-to-head bisbenzimidazole compounds (16 – 42) using the polyphosphoric acid method. These compounds were screened for their antibacterial activity and their antifungal activity. Compound 25 showed maximum potency against both Gram-positive and Gram-negative bacterial strains with minimum inhibitory concentration (MIC) values in the range of 7.81 – 31.25 μg/mL. In particular, it showed the maximum MIC values of 7.81 μg/mL against Gram-negative bacteria, which was four-fold more active than the standard drug ampicillin (MIC = 32.25 μg/mL). Compound 19 was found to be the most active against S. aureus with a MIC value of 3.90 μg/mL, whereas the remaining compounds showed only low-to-moderate activity. Furthermore, all compounds exhibited low activity against all fungal strains in comparison to the standard drug fluconazole. I addition, pharmacophore hypotheses were generated to analyze structure–activity relationships between the molecular structures and antimicrobial activities on E. coli. This pharmacophore model can be useful in order to design new antimicrobial drugs. It can be suggested that the substitution of a phenyl ring at the 5/6 and 5′/6′ positions in symmetric bisbenzimidazole derivatives produces compounds with promising antimicrobial activity.
- Ersan, Ronak Haj,Bolelli, Kayhan,Gonca, Serpil,Dogen, Aylin,Burmaoglu, Serdar,Algul, Oztekin
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p. 149 - 158
(2021/05/13)
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- Head-to-head bisbenzazole derivatives as antiproliferative agents: design, synthesis, in vitro activity, and SAR analysis
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Abstract: In the present work, a series of bisbenzazole derivatives were designed and synthesized as antiproliferative agents. The antiproliferative activity of these compounds was investigated using MTT assay. Bisbenzazole derivatives showed significant antiproliferative activity against all the four tested cancer cell lines. Among the various bisbenzazole derivatives, bisbenzoxazole derivatives exhibited the most promising anticancer activity followed by bisbenzimidazole and bisbenzothiazole derivatives. All the derivatives were found to be less toxic as compared to methotrexate (positive control) in normal human cells, indicating selective and efficient antiproliferative activity of these bisbenzazole derivatives. The structure–activity relationships of heteroaromatic systems and linkers present in bisbenzazole derivatives were analyzed in detail. In silico ADMET prediction revealed that bisbenzazole is a drug-like small molecule with a favorable safety profile. Compound 31 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from methotrexate. Graphic abstract: Twenty-one bisbenzoxazole derivatives have been designed synthesized and evaluated to be an antiproliferative activity against four human tumor cell lines.[Figure not available: see fulltext.]
- Ersan, Ronak Haj,Alagoz, Mehmet Abdullah,Ertan-Bolelli, Tugba,Duran, Nizami,Burmaoglu, Serdar,Algul, Oztekin
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p. 2247 - 2259
(2020/06/27)
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- CuO nano-particles supported on silica, a new catalyst for facile synthesis of benzimidazoles, benzothiazoles and benzoxazoles
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A facile synthetic route for benzimidazoles, benzothiazoles and benzoxazoles comprising the reaction of corresponding o-phenylenediamine, o-aminothiophenol and o-aminophenol with various aldehydes using silica supported nano-copper (II) oxide as a catalyst has been described. The catalyst exhibited clean reaction profile with excellent yields in a short reaction time. The catalyst can be recycled effectively after use.
- Inamdar, Suleman M.,More, Vinod K.,Mandal, Sisir K.
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p. 579 - 583
(2013/02/23)
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- An efficient and versatile synthesis of 2, 2′-(alkanediyl)-bis-1H- benzimidazoles employing aqueous fluoroboric acid as catalyst: Density functional theory calculations and fluorescence studies
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2,2′-(Alkanediyl)-bis-1H-benzimidazoles (simple and mixed) with variable methylene spacers were synthesized in excellent yields with aqueous fluoroboric acid (45%) (0.1 ml) as catalyst under solvent-free conditions. Their optimized structures were obtained using DFT calculations where it was seen that the s-trans orientation of the two imidazole rings was preferred for all types of bis-benzimidazole systems. The X-ray crystal structure of one such bis-benzimidazole further corroborated this fact. Finally, photophysical studies were carried out to get insight into the fluorescence characteristics of the newly synthesized bis-1H-benzimidazoles. ARKAT USA, Inc.
- Mukhopadhyay, Chhanda,Ghosh, Sabari,Butcher, Ray J.
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experimental part
p. 75 - 96
(2010/10/02)
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- Synthesis and anti-HIV activity of [ddN]-[ddN] dimers and benzimidazole nucleoside dimers
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In an attempt to combine the HIV-inhibitory capacity of different 2′,3′-dideoxynucleoside (ddN) analogs, we have designed and synthesized several dimers of [AZT]-[AZT] and [AZT]-[d4T]. In addition, we also synthesized the dimers of 1-(1H-benzimidazol-1-yl
- Li, Guo-Rui,Liu, Jun,Pan, Qin,Song, Zhi-Bin,Luo, Feng-Ling,Wang, Shao-Ru,Zhang, Xiao-Lian,Zhou, Xiang
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scheme or table
p. 2200 - 2208
(2010/07/17)
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