Benzimidazole and its derivatives: Recent Advances (2020–2022)

Ebenezer, Oluwakemi; Oyetunde-Joshua, Funsho; Omotoso, Oluwadamilare D.; Shapi, Micheal

doi:10.1016/j.rechem.2023.100925

Cited by 23 publications

(14 citation statements)

References 85 publications

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“…These dyes are known to tightly bind the minor groove of B-form DNA duplexes preferentially at A/T-rich stretches. − The core structure of Hoechst dyes, such as Hoechst 33258, is a bis-benzimidazole. The benzimidazole moieties form hydrogen bonding contacts to thymine O2-carbonyls and adenine N3-nitrogens, providing sequence specific recognition. , Additionally, the fluorescence properties of the benzimidazole moiety, which is enhanced upon binding nucleic acids, can be used as a reporter for DNA-binding. , Compared to bis-benzimidazoles, monobenzimidazole derivatives have also been reported as fluorescent DNA minor groove binders but are less challenging to synthesize. − Conjugation of monobenzimidazole derivatives to DNA is expected to provide fluorescent hybridization probes that have enhanced sequence specificity and stability properties as compared to unconjugated DNA. Furthermore, an evaluation of the hybridization properties of DNA-benzimidazole conjugates will inform on the generality of our approach and the utility of these probes for in vitro studies.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Sequence-Specific DNA Recognition Using Oligodeoxynucleotide-Benzimidazole Conjugates

Sur,

Pujari,

Ranjan

et al. 2024

ACS Bio Med Chem Au

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Synthetic modification of oligodeoxynucleotides (ODNs) via conjugation to nucleic acid binding small molecules can improve hybridization and pharmacokinetic properties. In the present study, five Hoechst 33258 derived benzimidazoles were conjugated to T rich ODNs and their hybridization effectiveness was tested. Thermal denaturation studies revealed significant stabilization of complementary duplexes by ODN-benzimidazole conjugates, with the extent of stabilization being highly dependent on the length of the linker between DNA and benzimidazole. The increases in thermal stability were determined to be due to the binding of the benzimidazole moiety to the duplex. Circular dichroism and molecular modeling studies provided insights toward the influence of conjugation on duplex structure and how linker length impacts placement of the benzimidazole moiety in the minor groove. Furthermore, thermal denaturation studies with the complementary strand containing a single base mismatch or being RNA revealed that covalent conjugation of benzimidazoles to an ODN also enhances the sequence specificity. The fundamental studies reported herein provide a strategy to improve the stability and specificity properties of the ODN probes, which can be of use for targeting and diagnostics applications.

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Section: Introductionmentioning

confidence: 99%

Enhanced Sequence-Specific DNA Recognition Using Oligodeoxynucleotide-Benzimidazole Conjugates

Sur,

Pujari,

Ranjan

et al. 2024

ACS Bio Med Chem Au

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“…Benzimidazole is widely used in antihypertensive, antituberculous, anti-inflammatory, antibacterial, antiviral, analgesic, antihypertensive, antibacterial, and rare applications in cardiovascular diseases. ,− Vitamin B12 consists of benzimidazole, and also thiabendazole, azomycin, chlotrimazole, mebendazole, Omeprazole and albendazole, rabeprazole are the important drugs composed of benzimidazole derivatives. , The synthesis of benzimidazole and quinazoline is 100% atom efficient due to 100% utilization of CO 2 and other substrates . Traditionally, benzimidazole was synthesized from DMF (dimethylformamide) derivatives, formic acid, esters, and methanol. − Benzimidazole was synthesized using a basic medium or strong medium, toxic reagents and high temperatures, but nowadays the synthesis is more environmentally friendly and sustainable by using catalysts. , Another important intermediate used in the pharmaceutical industry is quinazolines-2,4(1 H ,3 H )-diones synthesized by harmful chemicals such as anthranilamide with phosgene, anthranilic acid with urea, and antranilic acid with chlorosulfonyl isocyanate or potassium cyanate (Figure ). , Therefore, there is an urge to synthesize benzimidazole and quinazoline through an environmentally friendly, sustainable process as CO 2 is a low-cost and nontoxic C1 source.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Rajanna,

Srinivasappa,

Sudhakaran

et al. 2024

Energy Fuels

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CO 2 is an important component of the atmosphere that helps in balancing the Earth's atmospheric temperature and channelizes the food cycles. However, an increase or decrease in the concentration will severely affect the climate. Particularly, the rise in CO 2 levels has immensely contributed to global warming, resulting in elevated atmospheric temperature, altered precipitation patterns, glacier melting, and subsequent rises in sea levels, impacting human well-being. In response, researchers are exploring strategies to capture and convert CO 2 into valuable products, such as methanol, formic acid, and organic compounds. Particularly, the synthesis of organic compounds using CO 2 , like benzimidazole and quinazolines, has a high impact. Benzimidazole, widely used in medicinal chemistry for treating cancer and stomach ulcers, also exhibits antiviral and antifungal properties. Quinazoline derivatives, essential in drugs like prazosin and doxazosin, have applications in treating post-traumatic stress disorder and Alzheimer's disease. These compounds were synthesized mainly using environmentally harmful synthons such as phosgene and potassium cyanide. To address both environmental and health concerns, researchers are delving into the chemical fixation of CO 2 for sustainable and green production. Catalysis emerges as a key principle in green chemistry, with catalysts reducing activation energy and facilitating sustainable processes. This review discusses recent state of the art on the development of various catalysts for conversion of CO 2 to quinazoline and benzimidazole, through various homogeneous and heterogeneous catalysts. Notably, while homogeneous catalysts lack industrial recyclability, heterogeneous catalysts show promise for large-scale implementation. This comprehensive review discusses the mechanistic aspects with DFT studies in understanding the catalysts better. Toward the end, it gives the future scope and aspects on this subject.

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“…Among nitrogen-containing heterocycles, the benzimidazole scaffold, akin to the structural isostere of purine nucleotide bases, holds significance as a structural backbone in various clinically utilized antineoplastic drugs. Compounds like nocodazole, bendamustine, dovitinib, veliparip, pracinostat, liarozole, selumetinib, galeterone (Figure 1), among others, constitute part of this group [7][8][9][10]. Various benzimidazole derivatives with anticancer activity target different aspects of cancer cells, including DNA (through intercalation or alkylation), topoisomerases, poly (ADP ribose) polymerase (PARP), dihydrofolate reductase (DHFR), protein kinases and phosphatases, androgen receptors, and microtubules [7].…”

Section: Introductionmentioning

confidence: 99%

Self-Assembled Molecular Complexes of 1,10-Phenanthroline and 2-Aminobenzimidazoles: Synthesis, Structure Investigations, and Cytotoxic Properties

Anichina,

Kaloyanov,

Zasheva

et al. 2024

Molecules

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Three new molecular complexes (phen)3(2-amino-Bz)2(H+)(BF4−)·3H2O 5, (phen)3(2-amino-5(6)-methyl-Bz)2(H+)(BF4−)·H2O 6, and (phen)(1-methyl-2-amino-Bz)(H+)(BF4−) 7, were prepared by self-assembly of 1,10-phenanthroline (phen) and various substituted 2-aminobenzimidazoles. Confirmation of their structures was established through spectroscopic methods and elemental analysis. The X-ray diffraction analysis revealed that the crystal structure of 7 is stabilized by the formation of hydrogen bonds and short contacts. In addition, the molecular geometry and electron structure of molecules 5 and 6 were theoretically evaluated using density functional theory (DFT) methods. According to the DFT B3LYP/6-311+G* calculations, the protonated benzimidazole (Bz) units act as NH hydrogen bond donors, binding two phenanthrolines and a BF4− ion. Non-protonated Bz unit form hydrogen bonds with the N-atoms of a third molecule phen. The molecular assembly is held together by π-π stacking between benzimidazole and phenanthroline rings, allowing for N-atoms to associate with water molecules. The complexes were tested in vitro for their tumor cell growth inhibitory effects on prostate (PC3), breast (MDA-MB-231 and MCF-7), and cervical (HeLa) cancer cell lines using MTT-dye reduction assay. The in vitro cytotoxicity analysis and spectrophotometric investigation in the presence of ct-DNA, showed that self-assembled molecules 5–7 are promising DNA-binding anticancer agents warranting further in-depth exploration.

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Benzimidazole and its derivatives: Recent Advances (2020–2022)

Cited by 23 publications

References 85 publications

Enhanced Sequence-Specific DNA Recognition Using Oligodeoxynucleotide-Benzimidazole Conjugates

Enhanced Sequence-Specific DNA Recognition Using Oligodeoxynucleotide-Benzimidazole Conjugates

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Self-Assembled Molecular Complexes of 1,10-Phenanthroline and 2-Aminobenzimidazoles: Synthesis, Structure Investigations, and Cytotoxic Properties

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Benzimidazole and its derivatives: Recent Advances (2020–2022)

Cited by 23 publications

References 85 publications

Enhanced Sequence-Specific DNA Recognition Using Oligodeoxynucleotide-Benzimidazole Conjugates

Enhanced Sequence-Specific DNA Recognition Using Oligodeoxynucleotide-Benzimidazole Conjugates

Recent Advances in the Fixation of CO2 into Quinazoline and Benzimidazole

Self-Assembled Molecular Complexes of 1,10-Phenanthroline and 2-Aminobenzimidazoles: Synthesis, Structure Investigations, and Cytotoxic Properties

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Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole