Aryl-substituted aminobenzimidazoles targeting the hepatitis C virus internal ribosome entry site

Ding, Kejia; Wang, Annie; Boerneke, Mark A.; Dibrov, Sergey M.; Hermann, Thomas

doi:10.1016/j.bmcl.2014.05.009

Cited by 24 publications

(21 citation statements)

References 17 publications

(21 reference statements)

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“…Alkylations with alkyl halides have been extensively investigated in the literature . Diversely N ‐alkylated benzimidazol derivatives have been the focus of intensive investigations aiming at generating combinatorial libraries and contributing to the worldwide drug discovery efforts .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Structurally Diverse N‐Mono‐ and N,N′‐Disubstituted Benzimidazol‐2‐one Derivatives by the Alkylations of 1,3‐Dihydro‐2H‐benzimidazol‐2‐one with Some Alkyl Halides under Transfer Catalysis Conditions

Rohand

Fondjo

2018

Journal of Heterocyclic Chem

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A series of N‐mono‐ and N,N′‐disubstituted benzimidazol‐2‐one derivatives optionally substituted on both secondary amine functionalities were prepared with excellent yields by reacting 1,3‐dihydro‐2H‐benzimidazol‐2‐one in one and two steps respectively with various alkyl halides under phase transfer catalytic conditions. One of the synthesized N,N‐disubstituted benzimidazol‐2‐one derivatives underwent a regiospecific 1,3‐dipolar cycloaddition reaction at its side allyl substituent with the in situ generated 4‐chloro benzonitrile N‐oxide from 4‐chlorobenzaldoxime to afford in good yield the corresponding N,N′‐disubstituted derivative incorporating the 2,5‐dihydro‐isoxazole nucleus in one of the side chain. All the new compounds were fully characterized by their physical and spectroscopic data.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Structurally Diverse N‐Mono‐ and N,N′‐Disubstituted Benzimidazol‐2‐one Derivatives by the Alkylations of 1,3‐Dihydro‐2H‐benzimidazol‐2‐one with Some Alkyl Halides under Transfer Catalysis Conditions

Rohand

Fondjo

2018

Journal of Heterocyclic Chem

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“…The IRES subdomain IIa switch has been exploited as a therapeutic target to selectively suppress viral translation with synthetic inhibitors that capture specific conformations of the RNA (5,7,(9)(10)(11)(12). High levels of conservation in HCV clinical isolates and the presence of a deep solvent-excluded ligand binding pocket render the IIa RNA switch a target for the development of antiviral drugs.…”

Section: Significance and Applications Of The Iia Switchesmentioning

confidence: 99%

Ligand-responsive RNA mechanical switches

Boerneke

Hermann

2015

RNA Biology

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Ligand-responsive RNA mechanical switches represent a new class of simple switching modules that adopt well-defined ligand-free and bound conformational states, distinguishing them from metabolite-sensing riboswitches. Initially discovered in the internal ribosome entry site (IRES) of hepatitis C virus (HCV), these RNA switch motifs were found in the genome of diverse other viruses. Although large variations are seen in sequence and local secondary structure of the switches, their function in viral translation initiation that requires selective ligand recognition is conserved. We recently determined the crystal structure of an RNA switch from Seneca Valley virus (SVV) which is able to functionally replace the switch of HCV. The switches from both viruses recognize identical cognate ligands despite their sequence dissimilarity. Here, we describe the discovery of 7 new switches in addition to the previously established 5 examples. We highlight structural and functional features unique to this class of ligand-responsive RNA mechanical switches and discuss implications for therapeutic development and the construction of RNA nanostructures.

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“…1,2 N1-aryl-benzimidazole analogues have shown a variety of biological activities such as antihistaminic, anti-HIV, anti hepatitis C to name a few. [3][4][5] Literature survey has revealed that N1-aryl-benzimidazole analogues have significant potential as HIV-1 non-nucleoside reverse transcriptase inhibitors. [6][7][8][9][10][11][12] Molecular modeling study is an approach that is used to focus on the development of optimal models through variable selection and statistical methods to taper down to highly effective New Chemical Entities (NCE's).…”

Section: Acquired Immuno Deficiency Syndrome (Aids) Is a Viral Diseasmentioning

confidence: 99%

2D and 3D QSAR of Benzimidazole Analogues as Novel HIV-1 Non Nucleoside Reverse Transcriptase Inhibitors

Patil¹,

Asgaonkar²,

Chitre³

et al. 2017

IJPER

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Aryl-substituted aminobenzimidazoles targeting the hepatitis C virus internal ribosome entry site

Cited by 24 publications

References 17 publications

Synthesis of Novel Structurally Diverse N‐Mono‐ and N,N′‐Disubstituted Benzimidazol‐2‐one Derivatives by the Alkylations of 1,3‐Dihydro‐2H‐benzimidazol‐2‐one with Some Alkyl Halides under Transfer Catalysis Conditions

Synthesis of Novel Structurally Diverse N‐Mono‐ and N,N′‐Disubstituted Benzimidazol‐2‐one Derivatives by the Alkylations of 1,3‐Dihydro‐2H‐benzimidazol‐2‐one with Some Alkyl Halides under Transfer Catalysis Conditions

Ligand-responsive RNA mechanical switches

2D and 3D QSAR of Benzimidazole Analogues as Novel HIV-1 Non Nucleoside Reverse Transcriptase Inhibitors

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