A Jocic-type approach for a practical and scalable synthesis of pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents

被引：5

作者：

Federico, Stefano ^{[1
,2
]}

Khan, Tuhina ^{[1
]}

Relitti, Nicola ^{[1
]}

Chemi, Giulia ^{[1
,2
]}

Brindisi, Margherita ^{[1
,2
]}

Brogi, Simone ^{[1
,2
,3
]}

Novellino, Ettore ^{[3
]}

Zisterer, Daniela M. ^{[4
]}

Campiani, Giuseppe ^{[1
]}

Gemma, Sandra ^{[1
,2
]}

Butini, Stefania ^{[1
,2
]}

机构：

[1] Univ Siena, Dept Biotechnol Chem & Pharm, DoE 2018-2022,Via Aldo Moro 2, I-53100 Siena, Italy

[2] Univ Siena, Ist Toscano Tumori, Via Aldo Moro 2, I-53100 Siena, Italy

[3] Univ Naples Federico II, Dipartimento Farm, DoE 2018-2022,Via D Montesano 49, I-80131 Naples, Italy

[4] Trinity Coll Dublin, Sch Biochem & Immunol, Trinity Biomed Sci Inst, 152-160 Pearse St, Dublin 2, Ireland

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 51期

基金：

欧盟地平线“2020”;

关键词：

Pyrrolonaphthoxazepines; Jocic reaction; Aryl-alkyl ethers; Antitumor agents; PRIMER GRIP REGION; ENANTIOSELECTIVE SYNTHESIS; TRICHLOROMETHYL KETONES; BIOLOGICAL-ACTIVITY; ALPHA-AMINO; INHIBITORS; PYRROLO-1,5-BENZOXAZEPINE; PYRROLOBENZOXAZEPINE; SUBSTITUTION; DERIVATIVES;

D O I：

10.1016/j.tetlet.2018.11.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-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. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：4466 / 4470

页数：5

共 3 条

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