Solid phase synthesis of aryl and benzylpiperazines and their application in combinatorial chemistry

Dankwardt, Sharon M.; Newman, Sherry R.; Krstenansky, John L.

doi:10.1016/0040-4039(95)00930-b

Cited by 38 publications

(20 citation statements)

References 13 publications

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“…The current chemical literature is almost flooded with description of polymer-supported chemistries that provide a variety of heterocyclic compounds, amenable for the combinatorial synthesis of libraries. Those include β-lactam, 171,172 tetrahydrofuran, 173,174 benzofuran, 175 pyrroles, 163,172,[176][177][178][179] isoxazole, 180 thi- azolidine, 172,[181][182][183] imidazole, [184][185][186] benzimidazole, 187 hydantoins, 45,148,[188][189][190][191] benzopyran, 169 pyridine, [192][193][194][195][196][197] quinoline, 198,199 isoquinoline, [200][201][202][203][204] piperazine, 205,206 diketopiperazine, 112,127,154,[207]…”

Section: Heterocyclic Librariesmentioning

confidence: 99%

The “One-Bead-One-Compound” Combinatorial Library Method

1997

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Section: Heterocyclic Librariesmentioning

confidence: 99%

The “One-Bead-One-Compound” Combinatorial Library Method

1997

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“…Dankwardt and co-workers recently developed the solid phase synthesis of aryl and benzyl piperazine derivatives. 137 Nitro-activated aryl fluorides were reacted with a large variety of N-substituted piperazines to provide aryl piperazine derivatives 8 of high purity (Figure 15). When using electron-withdrawing groups such as the trifluoromethyl group, incomplete reaction was obtained.…”

Section: Compounds Containing Sulfurmentioning

confidence: 99%

“…Dankwardt and co-workers recently developed the solid phase synthesis of aryl and benzyl piperazine derivatives . Nitro-activated aryl fluorides were reacted with a large variety of N-substituted piperazines to provide aryl piperazine derivatives 8 of high purity (Figure ).…”

Section: B Cyclic Compounds With Two or More Heteroatoms1 Compounds C...mentioning

confidence: 99%

The Current Status of Heterocyclic Combinatorial Libraries

1997

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“…The most common precursor in the synthesis is 4‐fluoro‐3‐nitrobenzoic acid (55,56), or other aromatic system that contains flouro and nitro groups which are adjacent to each other (66). In such case, nucleophilic aromatic displacement (S N Ar) of the fluoride at the ipso position is achieved by commercially available amines (Scheme 1) (67,68). Upon successful fluoride replacement, the aromatic nitro group is reduced to the primary aromatic amine.…”

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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Solid phase synthesis of aryl and benzylpiperazines and their application in combinatorial chemistry

Cited by 38 publications

References 13 publications

The “One-Bead-One-Compound” Combinatorial Library Method

The “One-Bead-One-Compound” Combinatorial Library Method

The Current Status of Heterocyclic Combinatorial Libraries

Structure–Activity Relationships of Melanocortin Agonists Containing the Benzimidazole Scaffold

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