Solid-phase synthesis of substituted 1-phenyl-2-aminomethyl-benzimidazoles and 1-phenyl-2-thiomethyl-benzimidazoles

Tumelty, David; Schwarz, Matthias; Needels, Michael C.

doi:10.1016/s0040-4039(98)01672-4

Cited by 56 publications

(30 citation statements)

References 14 publications

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“…Upon successful fluoride replacement, the aromatic nitro group is reduced to the primary aromatic amine. It appears that the nitro reduction on solid support may be performed with variety of reducing reagents (55,69–71), but we have elected to utilize SnCl 2 × 2H 2 O in NMP (2.0 m ) strategy (56,70,71). Upon the aromatic nitro reduction, o ‐phenylendiamine on the solid support was subjected to the on‐resin cyclocondensation that is performed with variety of commercially available aldehydes in DMF.…”

Section: Discussionmentioning

confidence: 99%

Structure–Activity Relationships of Melanocortin Agonists Containing the Benzimidazole Scaffold

et al. 2007

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The melanocortin system has been implicated in regulating various physiological processes including pigmentation, energy homeostasis, obesity, steroidogenesis cardiovascular, and exocrine gland function. The five melanocortin receptors that belong to the super family of G protein-coupled receptors are stimulated by naturally occurring agonists. The aim of this research was focused on the design, synthesis, and pharmacological characterization of melanocortin ligands that contain the 1,2,5-trisubstituted benzimidazole scaffold. A series of benzimidazole analogues, with three points of diversity at positions 1, 2, and 5, were designed, synthesized, pharmacologically assayed at the mouse melanocortin receptors MC1R, MC3R, MC4R, and MC5R and resulted in ligands possessing a range of agonist activity from nm to no stimulation at up to 100 microM concentrations. This study demonstrates that the benzimidazole structure template can be appended with key melanocortin agonist amino acids for the design melanocortin receptor agonist ligands.

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Section: Discussionmentioning

confidence: 99%

Structure–Activity Relationships of Melanocortin Agonists Containing the Benzimidazole Scaffold

et al. 2007

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“…Similar synthetic strategies have been established for the construction of benzimidazole libraries on solid-support by employing insoluble [99,[103][104][105][106] and soluble [107][108][109][110][111][112] resins. Later, Mayer and co-workers [101] and many other researchers have linked the resin to 4-fluoro-3-nitrobenzoic acid to provide 4-nitroaryl intermediate (102), then following previous strategies provides the benzimidazole ring system (104).…”

Section: Strategy Imentioning

confidence: 99%

Recent Advances in the Solid-Phase Combinatorial Synthetic Strategies for the Quinoxaline, Quinazoline and Benzimidazole Based Privileged Structures

Kamal¹,

Reddy²,

Devaiah

et al. 2006

MRMC

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Quinoxaline, quinazoline and benzimidazole based templates have been synthesized on solid-support employing different methodologies. This review enlightens academic and industrial examples of combinatorial synthesis for this type of heterocycles that appeared in the literature in the last decade. Hence, some of the important synthetic strategies for the generation of quinoxaline, quinazoline and benzimidazole based privileged structures, and the important biological activities for these heterocycles have been highlighted. Further, benzothiadiazinone, thioxoquinazolinone, cinnoline and indazole are also examined in this review.

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“…Developing chemistry for the reduction of the nitro group on solid support (127-129) not only removed a potential metabolic liability but also created a new center for functionalization. Several (130)(131)(132)(133)(134)(135)(136).…”

Section: Reprintsmentioning

confidence: 99%

Library Design Concepts and Implementation Strategies*

Hobbs

Guo

2001

Journal of Receptors and Signal Transduction

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Solid-phase synthesis of substituted 1-phenyl-2-aminomethyl-benzimidazoles and 1-phenyl-2-thiomethyl-benzimidazoles

Cited by 56 publications

References 14 publications

Structure–Activity Relationships of Melanocortin Agonists Containing the Benzimidazole Scaffold

Structure–Activity Relationships of Melanocortin Agonists Containing the Benzimidazole Scaffold

Recent Advances in the Solid-Phase Combinatorial Synthetic Strategies for the Quinoxaline, Quinazoline and Benzimidazole Based Privileged Structures

Library Design Concepts and Implementation Strategies*

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