New substituted benzimidazole derivatives: a patent review (2013 – 2014)

Wang, Miao; Han, Xiao-Feng; Zhou, Zhiming

doi:10.1517/13543776.2015.1015987

Cited by 42 publications

(26 citation statements)

References 54 publications

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“…This situation calls for the development of milder and more specific anticancer drugs. Compounds having (benz)imidazole as a structural motif have been widely used in medicinal chemistry as drug development, and researchers are constantly looking new uses and applications of these heterocycles . A literature survey reveals that numerous (benz)imidazole‐based heterocyclic compounds exhibit anticancer activity …”

Section: Anticancer Activities Of (Benz)imidazole‐based Macrocyclesmentioning

confidence: 99%

Medicinal applications of (benz)imidazole‐ and indole‐based macrocycles

Patil

2017

Chem Biol Drug Des

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Macrocyclic chemistry is one of the emerging research areas in the chemical science.Macrocyclic compounds continue to attract significant attention due to their numerous possible applications particularly in the areas like biology, catalysis and industry.This review article summarizes the developments and advances in synthesis and medicinal applications of macrocyclic compounds derived from (benz)imidazoleand indole-based heterocycles. Important medicinal applications of (benz)imidazoleand indole-based macrocycles include antimicrobial and anticancer activities. The representative lead compounds in each series of macromolecules have been discussed. All these initial lead breakthroughs help validate the great potential of (benz) imidazole-and indole-based macrocyclic compounds as a class of effective medicinal agents. S P E C I A L I S S U E A R T I C L E Medicinal applications of (benz)imidazole-and indole-based macrocyclesA macrocycle is a compound that contains a cyclic structure of at least twelve or more atoms. Macrocyclic compounds are natural or synthetic polydentate compounds, containing their donor atoms either incorporated in or less commonly attached to a cyclic backbone. Macrocyclic compounds having heteroatoms are important compounds with broad spectrum of biological activities [1][2][3][4][5][6][7] apart from their potential applications in supramolecular chemistry, catalysis and new materials. [8,9] Over the last few years, macrocyclic chemistry has attracted lot of interest and has become a growing area of research in inorganic and organic chemistry in view of its biological importance. [1][2][3][4] Compared to linear peptide macromolecules, cyclic macromolecules provide improved stability and membrane permeability. These factors were clearly demonstrated in the development of hepatitis C virus (HCV) NS3 protease inhibitor, BILN2061. To optimize multiparameters such as aqueous solubility, microsomal stability and lipophilicity, Zapf et al. used the twelve-membered macrocycles as a promising platform to generate potent Hsp90 inhibitors. Their detailed study revealed that as ring size increased aqueous solubility and microsome stability were decreased whereas lipophilicity increased with increasing ring size.[ [10][11][12][13][14] Within different classes of macrocycles, (benz)imidazoleand indole-based macrocycles have received a great deal attention in drug discovery. These compounds exhibit biological activity as antimicrobial and anticancer agents because of their specific structures. Presently, the syntheses of (benz)imidazole-and indole-based macrocycles have received an increasing attention to synthetic (inorganic and organic) chemists and biologists. Therefore, the newly emerging interest in the antimicrobial and anticancer applications of (benz)imidazole-and indole-based macrocycles led us to examine the few accounts available in the recent literature dealing with this area of research. In this review article, we focus on the synthesis and biological applications such as antimicrobial and a...

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Section: Anticancer Activities Of (Benz)imidazole‐based Macrocyclesmentioning

confidence: 99%

Medicinal applications of (benz)imidazole‐ and indole‐based macrocycles

Patil

2017

Chem Biol Drug Des

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“…The benzimidazole ( 1 ) structural motif has been shown to be a significant pharmacophore and is also found in many natural products, including Vitamin B12. Consequently, there have been numerous recent reports on the synthesis and biological activities of diverse benzimidazole derivatives, and the patent literature from 2013–2015 attests to the importance of the benzimidazole structural moiety in drug design . Amongst the reported biological activities of benzimidazole derivatives are studies related to for example, their antibacterial, anticancer, antifungal, anti‐inflammatory and antiparasitic activities, which have been extensively reviewed and reported recently –…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Aryl‐ and 2‐Haloarylbenzimidazole‐N1‐acetamido Conjugates and a Preliminary Evaluation of Their Antifungal Properties

et al. 2018

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A series of new 2‐arylbenzimidazole‐N‐1 acetamido conjugates have been synthesized and characterized. Their antifungal activities were evaluated against fluconazole‐resistant C. albicans and A. fumigatus by the inhibition zone technique and were compared with the standard amphotericin B. Minimum inhibitory concentrations were determined for the most potent compounds, after preliminary structure‐activity analysis. Based upon these results a sub‐set of twelve ethylglycinyl ester conjugates bearing fluoro, chloro or bromo substituents on the 2‐phenyl moiety were examined for structure‐activity relationships using an agarose diffusion method employing a hypersensitive Sacharomyces cerevisiae strain. None of these compounds however showed significant activity at the concentrations tested. Single‐crystal X‐ray determinations were conducted on two of the newly synthesized compounds and were compared with DFT computational analysis.

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“…Their synthesis and applications have been recently reviewed in several articles [1][2][3][4][5][6][7][8]. Their great importance in medicinal chemistry has resulted in a large number of patent applications and has attracted great interest of the pharmaceutical industry [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…The condensation of 5,6-diamino-1,3-dimethyluracil (8) with isatoic anhydride (2a) leads to four distinct products. The first report [14] described the formation of 8-(2-aminophenyl)theophiline (9) and 1,3-dimethyl-11H-pyrido [4,5-b] [1,4]benzodiazepine-2,4,6(1H,3H,5H)-trione (10) with 22% and 17% yield, respectively. Furthermore, further investigation of the reaction [19] revealed formation of two additional products: 2,6-dimethylpurino [7,8-c]quinazoline-3,5,6(2H,4H,7H)-trione (11) (12% yield) and small amounts of tricycloquinazoline (12).…”

Section: Introductionmentioning

confidence: 99%

N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imid-azol-2-yl)benzeneamine

Dziełak

Trzybiński

Czerwińska

et al. 2018

Molbank

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N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)benzeneamine was obtained by condensation of N-(4-bromobenzyl)-3,1-benzoxazine-2,4-dione (N-(4-bromobenzyl)isatoic anhydride) with 4,5-dimethyl-1,2-phenylenediamine in refluxing acetic acid. This is a rare example of condensation of N-substituted 3,1-benzoxazine-2,4-dione with 1,2-phenylenediamine, which resulted in the formation of a benzimidazole derivative with a moderate yield. Crystallographic studies and initial biological screening were performed for the obtained product.

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New substituted benzimidazole derivatives: a patent review (2013 – 2014)

Cited by 42 publications

References 54 publications

Medicinal applications of (benz)imidazole‐ and indole‐based macrocycles

Medicinal applications of (benz)imidazole‐ and indole‐based macrocycles

Synthesis of 2‐Aryl‐ and 2‐Haloarylbenzimidazole‐N1‐acetamido Conjugates and a Preliminary Evaluation of Their Antifungal Properties

N-(4-Bromobenzyl)-2-(5,6-dimethyl-1H-benzo[d]imid-azol-2-yl)benzeneamine

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