从天然产物石蒜碱中制备结构多样的化合物。
Preparation of Structurally Diverse Compounds from the Natural Product Lycorine.
机构信息
Department of Chemistry, Roger Adams Laboratory , University of Illinois at Urbana-Champaign , 600 South Mathews Avenue , Urbana , Illinois 61801 , United States.
出版信息
Org Lett. 2018 Sep 21;20(18):5894-5898. doi: 10.1021/acs.orglett.8b02562. Epub 2018 Sep 11.
Abstract
The synthesis of a 52-member compound collection from the natural product lycorine is reported, highlighted by divergent cross-coupling and substitution strategies and an unusual ring rearrangement induced by reaction with aryne intermediates.
摘要
本文报道了从天然产物石蒜碱合成的 52 个成员的化合物库，其特点是采用了发散的交叉偶联和取代策略，以及通过与芳炔中间体反应诱导的不寻常的环重排。
相似文献
1
Preparation of Structurally Diverse Compounds from the Natural Product Lycorine.从天然产物石蒜碱中制备结构多样的化合物。
Org Lett. 2018 Sep 21;20(18):5894-5898. doi: 10.1021/acs.orglett.8b02562. Epub 2018 Sep 11.
2
Total synthesis of (-)-lycorine and (-)-2-epi-lycorine by asymmetric conjugate addition cascade.通过不对称共轭加成串联反应全合成(-)-石蒜碱和(-)-2-表石蒜碱
Org Lett. 2009 Apr 2;11(7):1631-3. doi: 10.1021/ol9003564.
3
Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids: total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent-lycoricidine.用于石蒜碱型石蒜科生物碱的化学酶法：对映-石蒜西定、3-表-对映-石蒜西定和4-脱氧-3-表-对映-石蒜西定的全合成
Org Lett. 2007 Aug 30;9(18):3683-5. doi: 10.1021/ol701552r. Epub 2007 Aug 8.
4
Catalytic asymmetric assembly of octahydroindolones: divergent synthesis of lycorine-type amaryllidaceae alkaloids (+)-α-lycorane and (+)-lycorine.八氢吲哚酮的催化不对称组装：石蒜碱型石蒜科生物碱（+）-α-石蒜烷和（+）-石蒜碱的发散合成
Chemistry. 2014 May 12;20(20):6112-9. doi: 10.1002/chem.201400178. Epub 2014 Apr 3.
5
Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement.通过环丙基开环重排全合成石蒜碱型生物碱。
Org Biomol Chem. 2014 May 28;12(20):3191-200. doi: 10.1039/c4ob00126e. Epub 2014 Apr 10.
6
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.通过从石蒜碱型前体的生物模拟环开关，全合成石蒜科生物碱 (+/-)-克利冯宁。
J Am Chem Soc. 2010 Apr 14;132(14):5176-8. doi: 10.1021/ja910184j.
7
Synthesis of the putative structure of (±)-amarbellisine.（±）-山柰酚的假定结构的合成。
Org Lett. 2013 Jan 18;15(2):410-3. doi: 10.1021/ol3034093. Epub 2012 Dec 28.
8
Asymmetric Total Syntheses of (-)-α-Lycorane, (-)-Zephyranthine, and Formal Synthesis of (+)-Clivonine.(-)-α-石蒜碱的不对称全合成、(-)-黄嘌呤的不对称全合成以及(+)-克利夫宁碱的形式合成
Chem Asian J. 2017 Jun 19;12(12):1309-1313. doi: 10.1002/asia.201700555. Epub 2017 May 31.
9
An efficient synthesis of (+/-)-Lycoricidine featuring a Stille-IMDAF cycloaddition cascade.一种通过Stille-IMDAF环加成串联反应高效合成（±）-石蒜碱的方法。
Org Lett. 2006 Jan 19;8(2):247-50. doi: 10.1021/ol052524f.
10
Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives.合成石蒜科成分和非天然衍生物。
Angew Chem Int Ed Engl. 2016 May 4;55(19):5642-91. doi: 10.1002/anie.201508227. Epub 2016 Mar 11.
引用本文的文献
1
Identification of a Selective Anticancer Agent from a Collection of Complex-And-Diverse Compounds Synthesized from Stevioside.从甜菊糖苷合成的复杂多样化合物集合中鉴定一种选择性抗癌剂。
J Am Chem Soc. 2025 Mar 26;147(12):10647-10661. doi: 10.1021/jacs.5c00919. Epub 2025 Mar 11.
2
Chloroformate-mediated ring cleavage of indole alkaloids leads to re-engineered antiplasmodial agents.氯甲酸酯介导的吲哚生物碱环裂解导致了经过改造的抗疟药物。
Org Biomol Chem. 2024 Oct 30;22(42):8423-8436. doi: 10.1039/d4ob00853g.
3
Influence of Sucrose and Activated Charcoal on Phytochemistry and Vegetative Growth in (Ravenna) Nic. García (Amaryllidaceae).蔗糖和活性炭对（拉文纳）烟草（茄科）植物化学和营养生长的影响。
需注意，你提供的原文中“(Ravenna) Nic. García (Amaryllidaceae)”存在一些错误信息，“Nic.”一般是“Nicotiana”（烟草属）的缩写，而烟草属是茄科，不是石蒜科（Amaryllidaceae），这里可能存在混淆。如果按照正确的信息来准确翻译，可能更准确的译文是：蔗糖和活性炭对烟草（拉文纳烟草，茄科）植物化学和营养生长的影响 。
Plants (Basel). 2024 Feb 20;13(5):569. doi: 10.3390/plants13050569.
4
Sanguinarine Exhibits Antiviral Activity against Porcine Reproductive and Respiratory Syndrome Virus via Multisite Inhibition Mechanisms.血根碱通过多靶点抑制机制抗猪繁殖与呼吸综合征病毒。
Viruses. 2023 Mar 6;15(3):688. doi: 10.3390/v15030688.
5
Target-Agnostic P-Glycoprotein Assessment Yields Strategies to Evade Efflux, Leading to a BRAF Inhibitor with Intracranial Efficacy.靶向无关的 P-糖蛋白评估产生了逃避外排的策略，从而导致具有颅内疗效的 BRAF 抑制剂。
J Am Chem Soc. 2022 Jul 13;144(27):12367-12380. doi: 10.1021/jacs.2c03944. Epub 2022 Jun 27.
6
Ring Distortion of Vincamine Leads to the Identification of Re-Engineered Antiplasmodial Agents.长春胺的环扭曲导致重新设计的抗疟药的鉴定。
ACS Omega. 2021 Jul 28;6(31):20455-20470. doi: 10.1021/acsomega.1c02480. eCollection 2021 Aug 10.
7
Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity.柚皮苷作为构建具有高支架多样性化合物的起点。
Angew Chem Int Ed Engl. 2021 Jul 12;60(29):16119-16128. doi: 10.1002/anie.202104228. Epub 2021 Jun 10.
8
Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.六脱氢狄尔斯-阿尔德反应：通过连接的三炔的环异构化生成苯炔
Chem Rev. 2021 Feb 24;121(4):2413-2444. doi: 10.1021/acs.chemrev.0c00825. Epub 2021 Jan 25.
9
Re-engineering natural products to engage new biological targets.对天然产物进行重新设计以作用于新的生物靶点。
Nat Prod Rep. 2020 Nov 18;37(11):1395-1403. doi: 10.1039/d0np00059k.
10
Re-Engineering of Yohimbine's Biological Activity through Ring Distortion: Identification and Structure-Activity Relationships of a New Class of Antiplasmodial Agents.通过环扭曲对育亨宾生物活性的再工程化：新型抗疟药物的鉴定和结构-活性关系。
ACS Infect Dis. 2020 Feb 14;6(2):159-167. doi: 10.1021/acsinfecdis.9b00380. Epub 2020 Jan 16.
本文引用的文献
1
Multiple biological functions and pharmacological effects of lycorine.石蒜碱的多种生物学功能及药理作用
Sci China Chem. 2013;56(10):1382-1391. doi: 10.1007/s11426-013-4967-9. Epub 2013 Aug 24.
2
Chemical probes and drug leads from advances in synthetic planning and methodology.从合成规划和方法学的进展中获得的化学探针和药物先导物。
Nat Rev Drug Discov. 2018 May;17(5):333-352. doi: 10.1038/nrd.2018.53. Epub 2018 Apr 13.
3
Second-generation DNA-templated macrocycle libraries for the discovery of bioactive small molecules.第二代 DNA 模板大环文库用于生物活性小分子的发现。
Nat Chem. 2018 Jul;10(7):704-714. doi: 10.1038/s41557-018-0033-8. Epub 2018 Apr 2.
4
Reagent-controlled regiodivergent ring expansions of steroids.试剂控制的甾体类化合物的区域发散性扩环反应。
Nat Commun. 2018 Mar 5;9(1):934. doi: 10.1038/s41467-018-03248-2.
5
Novel Topologically Complex Scaffold Derived from Alkaloid Haemanthamine.源自生物碱血根碱的新型拓扑复杂支架。
Molecules. 2018 Jan 28;23(2):255. doi: 10.3390/molecules23020255.
6
Synthesis and Demonstration of the Biological Relevance of sp -rich Scaffolds Distantly Related to Natural Product Frameworks.与天然产物骨架远缘相关的富含sp的支架的生物相关性的合成与论证
Chemistry. 2017 Oct 26;23(60):15227-15232. doi: 10.1002/chem.201704169. Epub 2017 Oct 6.
7
Reactions of hexadehydro-Diels-Alder benzynes with structurally complex multifunctional natural products.十六氢-Diels-Alder 苯炔与结构复杂的多功能天然产物的反应。
Nat Chem. 2017 Jun;9(6):523-530. doi: 10.1038/nchem.2732. Epub 2017 Feb 27.
8
Predictive compound accumulation rules yield a broad-spectrum antibiotic.预测性化合物积累规则产生一种广谱抗生素。
Nature. 2017 May 18;545(7654):299-304. doi: 10.1038/nature22308. Epub 2017 May 10.
9
A novel complexity-to-diversity strategy for the diversity-oriented synthesis of structurally diverse and complex macrocycles from quinine.一种新颖的从奎宁出发进行结构多样且复杂大环化合物的多样性导向合成的复杂性到多样性策略。
Bioorg Med Chem. 2017 Jun 1;25(11):2825-2843. doi: 10.1016/j.bmc.2017.02.060. Epub 2017 Feb 28.
10
DNA-encoded chemistry: enabling the deeper sampling of chemical space.DNA 编码化学：实现更深入的化学空间采样。
Nat Rev Drug Discov. 2017 Feb;16(2):131-147. doi: 10.1038/nrd.2016.213. Epub 2016 Dec 9.
Zotero 插件