Azepino- and Diazepinoindoles: Synthesis and Dopamine Receptor Binding Profiles

Kraxner, Johannes; H??bner, Harald; Gmeiner, Peter

doi:10.1002/1521-4184(20009)333:9<287::aid-ardp287>3.3.co;2-i

Cited by 5 publications

(6 citation statements)

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“…Initial attempts at converting this alcohol into a nitrile group by nucleophilic displacement of the corresponding mesylate with sodium cyanide were unsuccessful due to the sterically congested nature of the dibenzylic alcohol. Generating the chloride followed by reaction with TiCl 4 and trimethylsilylcyanide (TMSCN) successfully provided nitriles 48 and 49 . Nitrile reduction with lithium aluminum hydride and treatment with acid yielded the hydrochloride salts 15 and 16 in poor to modest yield.…”

Section: Resultsmentioning

confidence: 99%

Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

et al. 2007

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3-iodothyronamine (1, T1AM) is a naturally occurring derivative of thyroid hormone that can potently activate the orphan G protein-coupled receptor (GPCR) known as the trace amine-associated receptor 1 (TAAR1). We have previously found that modifying the outer ring of the phenoxyphenethylamine core scaffold of 1 can improve potency and provide potent agonists. In this study, we explored the tolerance of rat and mouse TAAR1 (rTAAR1 and mTAAR1) for structural modifications in the ethylamine portion of 1. We found that incorporating unsaturated hydrocarbon substituents and polar, hydrogen-bond-accepting groups were beneficial for rTAAR1 and mTAAR1, respectively, providing compounds that were equipotent or more potent than 1. Additionally, we have discovered that a naphthyl group is an excellent isosteric replacement for the iodophenyl ring of 1.

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Section: Resultsmentioning

confidence: 99%

Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

et al. 2007

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“…Here, we report a gold-catalyzed synthesis of oxepino- and diazepino[1,7- a ]indole derivatives 2 . These are important structural motifs found in hepatitis C virus polymerase and dopamine receptor-binding compounds . The reaction proceeds through regioselective 7- endo - dig cyclization starting from conjugated diynes 1 .…”

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confidence: 99%

Direct Construction of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Conjugated Diynes

et al. 2015

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“…In 2019, a chemoenzymatic route towards azepino[3,4,5‐ cd ]‐indoles was outlined by Zou et al , involving an enzyme catalysed PS reaction of a tryptamine analogue with the natural substrate secologanin, followed by chemical transformation to attain the biologically active product [169] . Molecules containing the azepino[3,4,5‐ cd ] indole core have displayed dopamine receptor binding activity, showing potential as drugs for neuropsychiatric diseases [170] . The group reported the PS reaction between tryptamine analogue 1 H ‐indole‐4‐ethanamine and secologanin catalysed by STR1 to furnish a tricyclic intermediate with >98 % de , which was subsequently cyclised to afford the corresponding lactam in 24 % isolated yield (Scheme 19).…”

Section: Emerging Enzymes For Biocatalytic C−c Bond Formationmentioning

confidence: 99%

New Trends and Future Opportunities in the Enzymatic Formation of C−C, C−N, and C−O bonds

et al. 2021

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Organic chemistry provides society with fundamental products we use daily. Concerns about the impact that the chemical industry has over the environment is propelling major changes in the way we manufacture chemicals. Biocatalysis offers an alternative to other synthetic approaches as it employs enzymes, Nature's catalysts, to carry out chemical transformations. Enzymes are biodegradable, come from renewable sources, operate under mild reaction conditions, and display high selectivities in the processes they catalyse. As a highly multidisciplinary field, biocatalysis benefits from advances in different areas, and developments in the fields of molecular biology, bioinformatics, and chemical engineering have accelerated the extension of the range of available transformations (E. L. Bell et al., Nat. Rev. Meth. Prim. 2021, 1, 1-21). Recently, we surveyed advances in the expansion of the scope of biocatalysis via enzyme discovery and protein engineering (J. R. Marshall et al., Tetrahedron 2021, 82, 131926). Herein, we focus on novel enzymes currently available to the broad synthetic community for the construction of new CÀ C, CÀ N and CÀ O bonds, with the purpose of providing the non-specialist with new and alternative tools for chiral and sustainable chemical synthesis.

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Azepino- and Diazepinoindoles: Synthesis and Dopamine Receptor Binding Profiles

Cited by 5 publications

References 0 publications

Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

Exploring the Structure−Activity Relationship of the Ethylamine Portion of 3-Iodothyronamine for Rat and Mouse Trace Amine-Associated Receptor 1

Direct Construction of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Conjugated Diynes

New Trends and Future Opportunities in the Enzymatic Formation of C−C, C−N, and C−O bonds

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