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Preparation of 3,5-methanobenzo[b]azepines: a novel sp3-rich Quinolone Isostere.

10 August 2023, Version 3
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The replacement of the aromatic ring in bioactive compounds with saturated bioisosteres has become a popular tactic to obtain novel structures with improved physicochemical profiles. In this communication, we describe an efficient synthesis of 3,5-methanobenzo[b]azepine analogs and suggest them as isosteres of quinolones. Quinolones are heteroaromatic, flat rings and considered as privileged scaffolds. An isosteric version of this scaffold with more 3D character would offer new options to expand their use.

Keywords

3D character
isosteres
methanobenzo[b]azepines
chemical space

Supplementary materials

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Description
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Supporting Information
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Experimental protocol and compounds characterizations NMR spectra of new compounds
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Version History

Aug 10, 2023 Version 3

Version Notes

1 author has been added more physchem properties has been added In the SI, more analysis have been added

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2023-6tv1z-v3
D O I: 10.26434/chemrxiv-2023-6tv1z-v3 [opens in a new tab]

Funding

European Union’s Hori-zon 2020
Research and Innovation Program Marie Sklodowska Curie Action ITN under Grant Agreement No 859458

Author’s competing interest statement

The authors are employees and CEO (T. C. F.) of SpiroChem AG, an Innovative Contract Research Organization (iCRO) commercializing synthesis services building blocks, fragments and virtual libraries.

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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