{"title":"无金属[3 + 3]和[4 + 2]级联环化二氢异喹啉和烯-炔-恶唑酮：吲哚异喹啉喹啉酰胺的合成。","authors":"Rattana Worayuthakarn, Phum Tachachartvanich, Rapeepat Sangsuwan, Somsak Ruchirawat, Nopporn Thasana","doi":"10.1002/chem.202502380","DOIUrl":null,"url":null,"abstract":"<p><p>A cascade cyclization of polycyclic indenoisoquinolinoquinolinamides has been realized via metal-free [3 + 3] and [4 + 2] intramolecular cyclization of ene-yne-oxazolones and dihydroisoquinoline under neutral conditions in good to excellent yield. In this process, three rings and four bonds are formed with high atom economy under reaction conditions that comply with green chemistry principles. The biological activity of the indenoisoquinolinoquinolinamide analogs, which mimic the structure of lamellarins-a group of marine natural products-was evaluated. The results indicated that these indenoisoquinolinoquinolinamide analogs exhibited notable anti-cancer activity, with cytotoxicity profiles comparable to those of their lamellarin counterparts.</p>","PeriodicalId":144,"journal":{"name":"Chemistry - A European Journal","volume":" ","pages":"e02380"},"PeriodicalIF":3.7000,"publicationDate":"2025-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Metal-Free [3 + 3] and [4 + 2] Cascade Cyclization of Dihydroisoquinolines and Ene-Yne-Oxazolones: Synthesis of Indenoisoquinolinoquinolinamides.\",\"authors\":\"Rattana Worayuthakarn, Phum Tachachartvanich, Rapeepat Sangsuwan, Somsak Ruchirawat, Nopporn Thasana\",\"doi\":\"10.1002/chem.202502380\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A cascade cyclization of polycyclic indenoisoquinolinoquinolinamides has been realized via metal-free [3 + 3] and [4 + 2] intramolecular cyclization of ene-yne-oxazolones and dihydroisoquinoline under neutral conditions in good to excellent yield. In this process, three rings and four bonds are formed with high atom economy under reaction conditions that comply with green chemistry principles. The biological activity of the indenoisoquinolinoquinolinamide analogs, which mimic the structure of lamellarins-a group of marine natural products-was evaluated. The results indicated that these indenoisoquinolinoquinolinamide analogs exhibited notable anti-cancer activity, with cytotoxicity profiles comparable to those of their lamellarin counterparts.</p>\",\"PeriodicalId\":144,\"journal\":{\"name\":\"Chemistry - A European Journal\",\"volume\":\" \",\"pages\":\"e02380\"},\"PeriodicalIF\":3.7000,\"publicationDate\":\"2025-10-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemistry - A European Journal\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/chem.202502380\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - A European Journal","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/chem.202502380","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Metal-Free [3 + 3] and [4 + 2] Cascade Cyclization of Dihydroisoquinolines and Ene-Yne-Oxazolones: Synthesis of Indenoisoquinolinoquinolinamides.
A cascade cyclization of polycyclic indenoisoquinolinoquinolinamides has been realized via metal-free [3 + 3] and [4 + 2] intramolecular cyclization of ene-yne-oxazolones and dihydroisoquinoline under neutral conditions in good to excellent yield. In this process, three rings and four bonds are formed with high atom economy under reaction conditions that comply with green chemistry principles. The biological activity of the indenoisoquinolinoquinolinamide analogs, which mimic the structure of lamellarins-a group of marine natural products-was evaluated. The results indicated that these indenoisoquinolinoquinolinamide analogs exhibited notable anti-cancer activity, with cytotoxicity profiles comparable to those of their lamellarin counterparts.
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Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields.
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