A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents
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2018Author:
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Daniela Zisterer, Stefano Federico, Tuhina Khan, Nicola Relitti, Giulia Chemi, Margherita Brindisi, Simone Brogi, Ettore Novellino, Giuseppe Campiani, Sandra Gemma, Stefania Butini, 'A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents', 2018, Tetrahedron Letters;Abstract:
We developed a Jocic-type protocol for the construction of the pyrrolonaphthoxazepine (PNOX) core.
After an initial investigation based on the isolation of a trichloromethyl carbinol derivative, we shifted
our attention towards a multicomponent single-step protocol. Screening of a variety of bases and solvents
led to the identification of the optimum conditions for the preparation of the key a-aryloxy carboxylic
acids to undergo intramolecular cyclization. The novel chemical route significantly improved overall
yields for the preparation of PNOX-based compounds and was successfully extended to the preparation
of 1,4-benzoxazinone-based templates.
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European Commission
MSCA ITN grant No 721906.
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Author: Zisterer, Daniela; Federico, Stefano; Khan, Tuhina; Relitti, Nicola; Chemi, Giulia; Brindisi, Margherita; Brogi, Simone; Novellino, Ettore; Campiani, Giuseppe; Gemma, Sandra; Butini, Stefania
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Tetrahedron Letters;Availability:
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Pyrrolonaphthoxazepines, apoptosis, heterocycles, anti-tumourSubject (TCD):
CancerDOI:
https://doi.org/10.1016/j.tetlet.2018.11.005Metadata
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