3-去羟基纳曲胺和N-甲基-3-去羟基纳曲胺的立体选择性合成。
Stereoselective syntheses of 3-dehydroxynaltrexamines and -methyl-3-dehydroxynaltrexamines.
作者信息
Li Mengchu, St Onge Celsey M, Zhang Yan
机构信息
Department of Medicinal Chemistry, Virginia Commonwealth University, 800 E Leigh St, Richmond, VA, 23298, USA.
出版信息
Tetrahedron Lett. 2020 Sep 24;61(39). doi: 10.1016/j.tetlet.2020.152379. Epub 2020 Aug 20.
Abstract
Methodology is presented for the synthesis of -dehydroxynaltrexamines and -methyl-3-dehydroxynaltrexamines. A stereoselective route is provided for each target compound while a novel one-pot method for the synthesis of 6 --methyl-3-dehydroxynaltrexamines is also explored. These results enable the versatile and efficient preparation of key epoxymorphinan intermediates to facilitate future selective opioid ligand discovery and development.
摘要
本文介绍了合成β-脱羟基纳曲胺和β-甲基-3-脱羟基纳曲胺的方法。为每种目标化合物提供了一条立体选择性路线，同时还探索了一种合成6-β-甲基-3-脱羟基纳曲胺的新型一锅法。这些结果使得能够通用且高效地制备关键的环氧吗啡喃中间体，以促进未来选择性阿片样物质配体的发现和开发。
相似文献
1
Stereoselective syntheses of 3-dehydroxynaltrexamines and -methyl-3-dehydroxynaltrexamines.3-去羟基纳曲胺和N-甲基-3-去羟基纳曲胺的立体选择性合成。
Tetrahedron Lett. 2020 Sep 24;61(39). doi: 10.1016/j.tetlet.2020.152379. Epub 2020 Aug 20.
2
The first example of the stereoselective synthesis of 7 beta-carbamoyl-4,5alpha-epoxymorphinan via a novel and reactive gamma-lactone.通过一种新型活性γ-内酯对7β-氨基甲酰基-4,5α-环氧吗啡喃进行立体选择性合成的首个实例。
Chem Pharm Bull (Tokyo). 2004 Jun;52(6):747-50. doi: 10.1248/cpb.52.747.
3
Efficient syntheses of chiral myo-inositol derivatives--key intermediates in glycosylphosphatidylinositol (GPI) syntheses.手性肌醇衍生物的高效合成——糖基磷脂酰肌醇（GPI）合成中的关键中间体。
Bioorg Med Chem Lett. 2009 Jul 15;19(14):3852-5. doi: 10.1016/j.bmcl.2009.03.151. Epub 2009 Apr 5.
4
Time and Pot Economy in Total Synthesis.全合成中的时间和物料经济性。
Acc Chem Res. 2021 Mar 16;54(6):1385-1398. doi: 10.1021/acs.accounts.0c00803. Epub 2021 Feb 22.
5
Stereoselective synthesis of unsymmetrical β,β-diarylacrylates by a Heck-Matsuda reaction: versatile building blocks for asymmetric synthesis of β,β-diphenylpropanoates, 3-aryl-indole, and 4-aryl-3,4-dihydro-quinolin-2-one and formal synthesis of (-)-indatraline.通过 Heck-Matsuda 反应立体选择性合成不对称 β,β-二芳基丙烯酸酯：不对称合成 β,β-二苯基丙酸盐、3-芳基吲哚和 4-芳基-3,4-二氢-喹啉-2-酮以及 (-)-吲达他林的全合成的多功能构建块。
J Org Chem. 2011 Feb 4;76(3):857-69. doi: 10.1021/jo102134v. Epub 2011 Jan 11.
6
Microbial/enzymatic synthesis of chiral drug intermediates.手性药物中间体的微生物/酶促合成
Adv Appl Microbiol. 2000;47:33-78. doi: 10.1016/s0065-2164(00)47001-2.
7
Multicomponent Hetero-[4 + 2] Cycloaddition/Allylboration Reaction: From Natural Product Synthesis to Drug Discovery.多组分杂[4+2]环加成/烯丙基硼化反应：从天然产物合成到药物发现。
Acc Chem Res. 2016 Nov 15;49(11):2489-2500. doi: 10.1021/acs.accounts.6b00403. Epub 2016 Oct 18.
8
Concepts for the syntheses of biotinylated steroids. Part II: 17beta-estradiol derivatives as immunochemical probes.生物素化甾体合成的概念。第二部分：作为免疫化学探针的17β-雌二醇衍生物
Bioconjug Chem. 2000 Jul-Aug;11(4):537-48. doi: 10.1021/bc9901651.
9
Exploitation of a Multienzymatic Stereoselective Cascade Process in the Synthesis of 2-Methyl-3-Substituted Tetrahydrofuran Precursors.多酶立体选择性级联反应在 2-甲基-3-取代四氢呋喃前体合成中的应用。
J Org Chem. 2017 Feb 17;82(4):2114-2122. doi: 10.1021/acs.joc.6b02927. Epub 2017 Jan 27.
10
Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp(3) C-H Functionalization.通过钯催化辅助导向的 sp(3) C-H 功能化合成与转化 α-氨基酸。
Acc Chem Res. 2016 Apr 19;49(4):635-45. doi: 10.1021/acs.accounts.6b00022. Epub 2016 Mar 25.
引用本文的文献
1
Systematic Structure-Activity Relationship Study of Nalfurafine Analogues toward Development of Potentially Nonaddictive Pain Management Treatments.纳曲酮类似物用于开发潜在非成瘾性疼痛管理治疗的系统构效关系研究
J Med Chem. 2024 Jun 13;67(11):9552-9574. doi: 10.1021/acs.jmedchem.4c00646. Epub 2024 May 30.
2
Characterization of a Potential KOR/DOR Dual Agonist with No Apparent Abuse Liability via a Complementary Structure-Activity Relationship Study on Nalfurafine Analogues.通过对纳呋拉啡类似物的互补结构-活性关系研究，鉴定一种潜在的 KOR/DOR 双重激动剂，且无明显滥用倾向。
ACS Chem Neurosci. 2022 Dec 21;13(24):3608-3628. doi: 10.1021/acschemneuro.2c00526. Epub 2022 Nov 30.
本文引用的文献
1
Pharmacological characterization of 17-cyclopropylmethyl-3,14-dihydroxy-4,5-epoxy-6-[(3'-fluoro-4'-pyridyl)acetamido]morphinan (NFP) as a dual selective MOR/KOR ligand with potential applications in treating opioid use disorder.17-环丙甲基-3,14-二羟基-4,5-环氧-6-[(3'-氟-4'-吡啶基)乙酰氨基]吗啡烷（NFP）作为一种双重选择性 MOR/KOR 配体的药理学特性及其在治疗阿片类药物使用障碍中的潜在应用。
Eur J Pharmacol. 2019 Dec 15;865:172812. doi: 10.1016/j.ejphar.2019.172812. Epub 2019 Nov 16.
2
Characterization of 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(indole-7-carboxamido)morphinan (NAN) as a Novel Opioid Receptor Modulator for Opioid Use Disorder Treatment.17-环丙甲基-3,14β-二羟基-4,5α-环氧-6α-(吲哚-7-羧酰胺基)吗啡烷（NAN）作为一种新型阿片受体调节剂用于治疗阿片类药物使用障碍的特征。
ACS Chem Neurosci. 2019 May 15;10(5):2518-2532. doi: 10.1021/acschemneuro.9b00038. Epub 2019 Feb 21.
3
Structure of the Nanobody-Stabilized Active State of the Kappa Opioid Receptor.纳米抗体稳定的κ阿片受体活性状态结构。
Cell. 2018 Jan 11;172(1-2):55-67.e15. doi: 10.1016/j.cell.2017.12.011. Epub 2018 Jan 4.
4
6β-N-Heterocyclic Substituted Naltrexamine Derivative BNAP: A Peripherally Selective Mixed MOR/KOR Ligand.6β-N-杂环取代的纳曲胺衍生物 BNAP：一种外周选择性混合 MOR/KOR 配体。
ACS Chem Neurosci. 2016 Aug 17;7(8):1120-9. doi: 10.1021/acschemneuro.6b00075. Epub 2016 Jun 15.
5
Structural insights into µ-opioid receptor activation.μ-阿片受体激活的结构见解
Nature. 2015 Aug 20;524(7565):315-21. doi: 10.1038/nature14886. Epub 2015 Aug 5.
6
Essential structure of the κ opioid receptor agonist nalfurafine for binding to the κ receptor.κ阿片受体激动剂纳呋拉啡与κ受体结合的基本结构。
Curr Pharm Des. 2013;19(42):7400-14. doi: 10.2174/138161281942140105165011.
7
Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 3: synthesis of decahydro(iminoethano)phenanthrene derivatives with an oxygen functionality at the 3-position and their pharmacologies.阿片 κ 受体激动剂纳呋拉啡与 κ 受体结合的必需结构：在 3 位具有氧官能团的十氢（亚氨基乙氧基）菲啶衍生物的合成及其药理学。
Bioorg Med Chem Lett. 2012 Dec 15;22(24):7711-4. doi: 10.1016/j.bmcl.2012.09.101. Epub 2012 Oct 5.
8
6β-N-heterocyclic substituted naltrexamine derivative NAP as a potential lead to develop peripheral mu opioid receptor selective antagonists.6β-N-杂环取代的纳曲胺衍生物 NAP 有望成为开发外周 μ 阿片受体选择性拮抗剂的先导化合物。
Bioorg Med Chem Lett. 2012 Jul 15;22(14):4731-4. doi: 10.1016/j.bmcl.2012.05.075. Epub 2012 May 26.
9
Structure of the human κ-opioid receptor in complex with JDTic.人κ-阿片受体与 JDTic 复合物的结构。
Nature. 2012 Mar 21;485(7398):327-32. doi: 10.1038/nature10939.
10
Crystal structure of the µ-opioid receptor bound to a morphinan antagonist.μ-阿片受体与吗啡喃拮抗剂结合的晶体结构
Nature. 2012 Mar 21;485(7398):321-6. doi: 10.1038/nature10954.
Zotero 插件