دورية أكاديمية
Total synthesis of 1,4a-di- epi-ent -pancratistatin, exemplifying a stereodivergent approach to pancratistatin isomers.
| العنوان: | Total synthesis of 1,4a-di- epi-ent -pancratistatin, exemplifying a stereodivergent approach to pancratistatin isomers. |
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| المؤلفون: | Sun C; Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan. yamak@tokushima-u.ac.jp., Inokuma T; Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan. yamak@tokushima-u.ac.jp.; Research Cluster on 'Key Material Development', Tokushima University, Shomachi, Tokushima 770-8505, Japan., Tsuji D; Faculty of Pharmacy, Yasuda Women's University, Asaminami-ku, Hiroshima 731-0153, Japan., Yamaoka Y; School of Pharmacy, Hyogo Medical University, Chuo-ku, Kobe, Hyogo 650-8530, Japan., Akagi R; Faculty of Pharmacy, Yasuda Women's University, Asaminami-ku, Hiroshima 731-0153, Japan., Yamada KI; Graduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan. yamak@tokushima-u.ac.jp.; Research Cluster on 'Key Material Development', Tokushima University, Shomachi, Tokushima 770-8505, Japan. |
| المصدر: | Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Jun 27; Vol. 60 (53), pp. 6757-6760. Date of Electronic Publication: 2024 Jun 27. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 9610838 Publication Model: Electronic Cited Medium: Internet ISSN: 1364-548X (Electronic) Linking ISSN: 13597345 NLM ISO Abbreviation: Chem Commun (Camb) Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Cambridge : Royal Society of Chemistry |
| مواضيع طبية MeSH: | Amaryllidaceae Alkaloids*/chemistry , Amaryllidaceae Alkaloids*/pharmacology , Amaryllidaceae Alkaloids*/chemical synthesis, Humans ; Stereoisomerism ; Cell Line, Tumor ; Isoquinolines/chemistry ; Isoquinolines/pharmacology ; Isoquinolines/chemical synthesis ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Drug Screening Assays, Antitumor ; Molecular Structure ; Cell Proliferation/drug effects ; Structure-Activity Relationship ; Cell Survival/drug effects |
| مستخلص: | The total synthesis of 1,4a-di- epi-ent -pancratistatin, a novel stereoisomer of the anti-tumor Amaryllidaceae alkaloid pancratistatin, was achieved in 14 steps starting from D-mannitol. The construction of the pancratistatin skeleton involved conjugate addition of organocuprate to a nitrosoolefin, which was generated in situ from inosose oxime. This was followed by stereoselective reduction of the oxime to an amine and site-selective formylation. Biological evaluations revealed that the newly synthesized compounds exhibit cytotoxicity toward cancer cells and significant ferroptosis inhibitory activity. These compounds constitute a promising small-molecule library for the development of potent bioactive agents. |
| المشرفين على المادة: | 0 (Amaryllidaceae Alkaloids) 96281-31-1 (pancratistatin) 0 (Isoquinolines) 0 (Antineoplastic Agents) |
| تواريخ الأحداث: | Date Created: 20240612 Date Completed: 20240627 Latest Revision: 20240627 |
| رمز التحديث: | 20240627 |
| DOI: | 10.1039/d4cc02199a |
| PMID: | 38864269 |
| قاعدة البيانات: | MEDLINE |
| تدمد: | 1364-548X |
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| DOI: | 10.1039/d4cc02199a |