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A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents |
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| Authors: | Stefano Federico Tuhina Khan Nicola Relitti Giulia Chemi Margherita Brindisi Simone Brogi Ettore Novellino Daniela M Zisterer Giuseppe Campiani Sandra Gemma Stefania Butini |
| Institution: | 1. Department of Biotechnology, Chemistry and Pharmacy, DoE 2018-2022, University of Siena, Via Aldo Moro, 2, 53100 Siena, Italy;2. Istituto Toscano Tumori, University of Siena, via Aldo Moro 2, I-53100, Siena, Italy;3. Dipartimento di Farmacia, DoE 2018-2022, University of Naples Federico II, via D. Montesano 49, 80131 Naples, Italy;4. School of Biochemistry and Immunology, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland |
| 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 α-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. |
| Keywords: | Pyrrolonaphthoxazepines Jocic reaction Aryl-alkyl ethers Antitumor agents |
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