دورية أكاديمية
Pharmacophore-Directed Retrosynthesis Applied to Ophiobolin A: Simplified Bicyclic Derivatives Displaying Anticancer Activity.
| العنوان: | Pharmacophore-Directed Retrosynthesis Applied to Ophiobolin A: Simplified Bicyclic Derivatives Displaying Anticancer Activity. |
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| المؤلفون: | Tao Y, Reisenauer KN, Masi M; Dipartimento di Scienze Chimiche, Complesso Universitario Monte Sant' Angelo, Naples, Italy., Evidente A; Dipartimento di Scienze Chimiche, Complesso Universitario Monte Sant' Angelo, Naples, Italy., Taube JH, Romo D |
| المصدر: | Organic letters [Org Lett] 2020 Nov 06; Vol. 22 (21), pp. 8307-8312. Date of Electronic Publication: 2020 Oct 09. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Washington, DC : American Chemical Society, c1999- |
| مواضيع طبية MeSH: | Antineoplastic Agents/*chemical synthesis , Antineoplastic Agents/*pharmacology , Sesterterpenes/*chemical synthesis , Sesterterpenes/*pharmacology, Antineoplastic Agents/chemistry ; Cell Line, Tumor ; Chemistry Techniques, Synthetic ; Humans ; Sesterterpenes/chemistry ; Structure-Activity Relationship |
| مستخلص: | Pharmacophore-directed retrosynthesis applied to ophiobolin A led to bicyclic derivatives that were synthesized and display anticancer activity. Key features of the ultimate defensive synthetic strategy include a Michael addition/facially selective protonation sequence to set the critical C6 stereocenter and a ring-closing metathesis to form the cyclooctene. Cytotoxicity assays toward a breast cancer cell line (MDA-MB-231) confirm the anticipated importance of structural complexity for selectivity (vs MCF10A cells) while C3 variations modulate stability. |
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| معلومات مُعتمدة: | R35 GM134910 United States GM NIGMS NIH HHS; R37 GM052964 United States GM NIGMS NIH HHS |
| المشرفين على المادة: | 0 (Antineoplastic Agents) 0 (Sesterterpenes) 4611-05-6 (ophiobolin A) |
| تواريخ الأحداث: | Date Created: 20201009 Date Completed: 20210827 Latest Revision: 20240330 |
| رمز التحديث: | 20240330 |
| مُعرف محوري في PubMed: | PMC7655722 |
| DOI: | 10.1021/acs.orglett.0c02938 |
| PMID: | 33034457 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1523-7052 |
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| DOI: | 10.1021/acs.orglett.0c02938 |