Identification of a series of benzoxazoles as potent 5-HT6 ligands

Liu, Kevin G.; Lo, Jennifer R.; Comery, Thomas A.; Zhang, Guo Ming; Zhang, Jean Y.; Kowal, Dianne; Smith, Deborah L.; Di, Li; Kerns, Edward H.; Schechter, Lee E.; Robichaud, Albert J.

doi:10.1016/j.bmcl.2008.12.107

Cited by 56 publications

(12 citation statements)

References 14 publications

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“…Both compounds were found to be full antagonists in ac yclic adenosine 5'-monophosphate (AMP) functional assay. [177] Aminobenzoxazole carboxamide-basedc ompounds 130, 131,a nd 132 were also discovered as potent 5-HT3 receptor antagonists for the treatment of diarrhea-predominant irritable bowels yndrome (IBS-D,F igure 57). [178] All three compounds were active when administered orally to mice and blocked the 5-HT-induced transient bradycardia (Table 16).…”

Section: Other Therapeutic Targetsmentioning

confidence: 99%

Recent Advances in the Development of Pharmacologically Active Compounds that Contain a Benzoxazole Scaffold

et al. 2015

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In recenty ears, the emergence of biologically active compounds that contain ah eterocyclic ring has gained ag reat deal of attention among medicinal chemists. Among these, benzoxazole-based compounds are particularly attractive because of their wide range of pharmacological activities. In this focus review, we highlight recent advancements in the development of benzoxazole-based pharmacologically active compounds since the year 2000.

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Section: Other Therapeutic Targetsmentioning

confidence: 99%

Recent Advances in the Development of Pharmacologically Active Compounds that Contain a Benzoxazole Scaffold

et al. 2015

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“…156 ; K i = 7.1 nM) [51]. Might these represent conformationally constrained analogs of 140 ; is the intact piperazine moiety required for binding?…”

Section: Other Core Modificationsmentioning

confidence: 99%

The Medicinal Chemistry of 5-HT6 Receptor Ligands with a Focus on Arylsulfonyltryptamine Analogs

Glennon

Siripurapu

Roth³

et al. 2010

CTMC

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Arylsulfonyl analogs of aminopyrimidines (e.g. Ro 04-6790; 2), aminopyridines (e.g. Ro 63-0563; 3), 1-phenylpiperazines (e.g. SB-271046; 4), and tryptamines (e.g. MS-245; 5) were described as the first examples of selective 5-HT6 receptor antagonists only ten years ago. Today, hundreds of compounds of seemingly diverse structure have been reported. The early antagonists featured an arylsulfonyl group leading to the widespread assumption that an arylsulfonyl moiety might be critical for binding and antagonist action. With respect to the arylsulfonyltryptamines, it seems that neither the “arylsulfonyl” nor the “tryptamine” portion of these compounds is essential for binding or for antagonist action, and some such derivatives even display agonist action. The present review describes many of the currently available 5-HT6 receptor ligands and, unlike prior reviews, provides a narrative of the thinking (where possible) that led to their design, synthesis, and evaluation. The arylsulfonyltryptamines are also used as the structural basis of attempts to relate various structure-types to one another to afford a better understanding of the overall structural requirements for 5-HT6 receptor binding.

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“…Amino-substituted azoles and their derivatives are ubiquitous in functional materials, pharmaceuticals, and natural products [ 1 , 2 , 3 ]. Among them, the 2-aminobenzoxazoles have already been described as potent 5-HT 3 -receptor antagonists [ 4 , 5 ], which are promising targets for the treatment of Alzheimer’s disease and schizophrenia.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of 2-Aminobenzoxazoles Using Reusable Ionic Liquid as a Green Catalyst under Mild Conditions

et al. 2017

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A facile, green, and efficient method for the direct oxidative amination of benzoxazoles using heterocyclic ionic liquid as catalyst has been developed. The reaction proceeded smoothly at room temperature and gave the desirable 2-aminobenzoxazoles with good to excellent yields (up to 97%). The catalyst 1-butylpyridinium iodide can be easily recycled and reused with similar efficacies for at least four cycles.

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Identification of a series of benzoxazoles as potent 5-HT6 ligands

Cited by 56 publications

References 14 publications

Recent Advances in the Development of Pharmacologically Active Compounds that Contain a Benzoxazole Scaffold

Recent Advances in the Development of Pharmacologically Active Compounds that Contain a Benzoxazole Scaffold

The Medicinal Chemistry of 5-HT6 Receptor Ligands with a Focus on Arylsulfonyltryptamine Analogs

The Synthesis of 2-Aminobenzoxazoles Using Reusable Ionic Liquid as a Green Catalyst under Mild Conditions

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