Design, synthesis, and anti-tumor evaluation of novel symmetrical bis-benzimidazoles

Yang, Yanhui; Cheng, Maosheng; Wang, Qing-He; Nie, Han; Liao, Na; Chen, Hong

doi:10.1016/j.ejmech.2008.07.021

Cited by 46 publications

(18 citation statements)

References 11 publications

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“…Benzimidazole is an important pharmacophore and ap rivileged structure in medicinal chemistry encompassing adiverse range of biological activities [1]. Series of DNA-interactive benzimidazole analogues, such as Hoechst 33258 [2], were also prepared to explore the potential for anticancer activity mediated for certain of drugs via bio-reductive activation by endogenous nicotinamide adenine dinucleotide or nicotinamide adenine dinucleotide 2'-phosphate reduced tetrasodium salt [3]. Our research group has focused on the synthesis of benzimidazole analogues.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-(2-amino-5-chlorophenyl)-1H-benzimidazole, C13H10ClN3

Wang¹,

Li²,

Lin³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-(2-amino-5-chlorophenyl)-1H-benzimidazole, C13H10ClN3

Wang¹,

Li²,

Lin³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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“…28 Compound 10e was obtained by reaction of compound 9b with CNBr. 29 In another synthesis, compound 9a on reaction 30 with CS 2 and KOH gave imidazol-2-thione 10b , whereas reaction of 9a with 1,1′-carbonyldiimidazole resulted 31 in imidazol-2-one 10c .…”

Section: Chemistrymentioning

confidence: 99%

Modification of agonist binding moiety in hybrid derivative 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-1-ol/-2-amino versions: Impact on functional activity and selectivity for dopamine D2/D3 receptors

Gopishetty

Zhang

Kharkar

et al. 2013

Bioorganic & Medicinal Chemistry

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The goal of the present study was to explore, in our previously developed hybrid template, the effect of introduction of additional heterocyclic rings (mimicking catechol hydroxyl groups as bioisosteric replacement) on selectivity and affinity for the D3 versus D2 receptor. In addition, we wanted to explore the effect of derivatization of functional groups of the agonist binding moiety in compounds developed by us earlier from the hybrid template. Binding affinity (Ki) of the new compounds was measured with tritiated spiperone as the radioligand and HEK-293 cells expressing either D2 or D3 receptors. Functional activity of selected compounds was assessed in the GTPγS binding assay. In the imidazole series, compound 10a exhibited the highest D3 affinity whereas the indole derivative 13 exhibited similar high D3 affinity. Functionalization of the amino group in agonist (+)-9d with different sulfonamides derivatives improved the D3 affinity significantly with (+)-14f exhibiting the highest affinity. However, functionalization of the hydroxyl and amino groups of 15 and (+)-9d, known agonist and partial agonist, to sulfonate ester and amide in general modulated the affinity. In both cases loss of agonist potency resulted from such derivatization.

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“…Therefore, the search for anticancer agents continues at various laboratories. Recently, different authors worldwide have reported antitumor, antiproliferative or anticancer potential of benzimidazole [1][2][3][4] and pyrazoline derivatives [5,6]. It gave us immense confidence to carry out work on pyrazoline with antitubercular and antiproliferative activity [7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%