高选择性 GPR30 激动剂 G-1 及其相关四氢喹啉类似物的高效合成与表征。
Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.
机构信息
Department of Chemistry and Biochemistry MSC 3C, New Mexico State University, P.O. Box 30001, Las Cruces, New Mexico 88003, USA.
出版信息
Org Biomol Chem. 2010 May 7;8(9):2252-9. doi: 10.1039/c001307b. Epub 2010 Mar 16.
Abstract
The GPR30 agonist probe G-1 and structural analogs were efficiently synthesized using multicomponent or stepwise Sc(III)-catalyzed aza-Diels-Alder cyclization. Optimization of solvent and reaction temperature provided enhanced endo-diastereoselectivity.
摘要
使用多组分或逐步 Sc(III)催化的氮杂-Diels-Alder 环化反应，高效合成了 GPR30 激动剂探针 G-1 和结构类似物。优化溶剂和反应温度可提高内型立体选择性。
相似文献
1
Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.高选择性 GPR30 激动剂 G-1 及其相关四氢喹啉类似物的高效合成与表征。
Org Biomol Chem. 2010 May 7;8(9):2252-9. doi: 10.1039/c001307b. Epub 2010 Mar 16.
2
Interrupted imino-Nazarov cyclization of 1-aminopentadienyl cation and related cascade process.1-氨戊二烯阳离子的中断亚胺-Nazarov 环化反应和相关级联过程。
Angew Chem Int Ed Engl. 2014 Sep 26;53(40):10742-6. doi: 10.1002/anie.201405251. Epub 2014 Aug 11.
3
Asymmetric three-component inverse electron-demand aza-Diels-Alder reaction: efficient synthesis of ring-fused tetrahydroquinolines.不对称三组分逆电子需求氮杂狄尔斯-阿尔德反应：稠环四氢喹啉的高效合成
Angew Chem Int Ed Engl. 2010 May 17;49(22):3799-802. doi: 10.1002/anie.201000590.
4
A new efficient synthesis of pyranoquinolines from 1-acetyl N-aryl cyclopentanecarboxamides.一种由1-乙酰基-N-芳基环戊烷甲酰胺高效合成吡喃并喹啉的新方法。
Org Lett. 2007 Aug 30;9(18):3651-3. doi: 10.1021/ol701536q. Epub 2007 Aug 3.
5
Beneficial role of the GPR30 agonist G-1 in an animal model of multiple sclerosis.GPR30激动剂G-1在多发性硬化症动物模型中的有益作用。
J Neuroimmunol. 2009 Sep 29;214(1-2):67-77. doi: 10.1016/j.jneuroim.2009.06.023. Epub 2009 Aug 6.
6
Cationic Pd(II)-Catalyzed Cyclization of N-Tosyl-aniline Tethered Allenyl Aldehydes with Arylboronic Acids: Diastereo- and Enantioselective Synthesis of Tetrahydroquinoline Derivatives.钯(II)催化 N-对甲苯磺酰基苯胺与芳基硼酸连接的烯丙基醛的环化反应：四氢喹啉衍生物的非对映选择性和对映选择性合成。
Org Lett. 2015 Aug 7;17(15):3910-3. doi: 10.1021/acs.orglett.5b01894. Epub 2015 Jul 24.
7
Insulinotropic and antidiabetic effects of 17β-estradiol and the GPR30 agonist G-1 on human pancreatic islets.17β-雌二醇和 GPR30 激动剂 G-1 对人胰腺胰岛的促胰岛素和抗糖尿病作用。
Endocrinology. 2011 Jul;152(7):2568-79. doi: 10.1210/en.2010-1361. Epub 2011 Apr 26.
8
Catalytic Dual 1,1-H-Abstraction/Insertion for Domino Spirocyclizations.催化双 1,1-H-抽提/插入的串联环化反应。
J Am Chem Soc. 2015 Jul 22;137(28):8928-31. doi: 10.1021/jacs.5b05735. Epub 2015 Jul 8.
9
Activation of GPR30 attenuates diastolic dysfunction and left ventricle remodelling in oophorectomized mRen2.Lewis rats.GPR30 的激活可减轻去卵巢 mRen2.Lewis 大鼠的舒张功能障碍和左心室重构。
Cardiovasc Res. 2012 Apr 1;94(1):96-104. doi: 10.1093/cvr/cvs090. Epub 2012 Feb 10.
10
An efficient synthesis of new C-2 aryl substituted quinolines based on three component imino Diels-Alder reaction.
Mol Divers. 2006 Feb;10(1):29-37. doi: 10.1007/s11030-006-2344-8.
引用本文的文献
1
LNS8801: An Enantiomerically Pure Agonist of the G Protein-Coupled Estrogen Receptor Suitable for Clinical Development.LNS8801：一种对映体纯的G蛋白偶联雌激素受体激动剂，适用于临床开发。
Cancer Res Commun. 2025 Apr 1;5(4):556-568. doi: 10.1158/2767-9764.CRC-24-0632.
2
G Protein-Coupled Estrogen Receptor GPER: Molecular Pharmacology and Therapeutic Applications.G 蛋白偶联雌激素受体 GPER：分子药理学和治疗应用。
Annu Rev Pharmacol Toxicol. 2023 Jan 20;63:295-320. doi: 10.1146/annurev-pharmtox-031122-121944.
3
Sequential ligand- and structure-based virtual screening approach for the identification of potential G protein-coupled estrogen receptor-1 (GPER-1) modulators.用于鉴定潜在G蛋白偶联雌激素受体-1（GPER-1）调节剂的基于配体和结构的序贯虚拟筛选方法。
RSC Adv. 2019 Jan 21;9(5):2525-2538. doi: 10.1039/c8ra09318k. eCollection 2019 Jan 18.
4
Modifications on the Tetrahydroquinoline Scaffold Targeting a Phenylalanine Cluster on GPER as Antiproliferative Compounds against Renal, Liver and Pancreatic Cancer Cells.针对GPER上苯丙氨酸簇修饰四氢喹啉骨架作为抗肾、肝和胰腺癌细胞增殖化合物的研究
Pharmaceuticals (Basel). 2021 Jan 10;14(1):49. doi: 10.3390/ph14010049.
5
Preclinical efficacy of the GPER-selective agonist G-1 in mouse models of obesity and diabetes.GPER 选择性激动剂 G-1 在肥胖和糖尿病小鼠模型中的临床前疗效。
Sci Transl Med. 2020 Jan 29;12(528). doi: 10.1126/scitranslmed.aau5956.
6
A Selective Ligand for Estrogen Receptor Proteins Discriminates Rapid and Genomic Signaling.一种选择性的雌激素受体蛋白配体可区分快速和基因组信号转导。
Cell Chem Biol. 2019 Dec 19;26(12):1692-1702.e5. doi: 10.1016/j.chembiol.2019.10.009. Epub 2019 Nov 6.
7
Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with -Aryl Imines: Synthesis of Tetrahydroquinolines.金催化炔醇与芳基亚胺的氢烷氧基化/波瓦罗夫反应串联：四氢喹啉的合成
ACS Omega. 2019 Sep 9;4(13):15754-15763. doi: 10.1021/acsomega.9b02693. eCollection 2019 Sep 24.
8
Role of GPER in estrogen-dependent nitric oxide formation and vasodilation.G蛋白偶联雌激素受体（GPER）在雌激素依赖性一氧化氮生成和血管舒张中的作用。
J Steroid Biochem Mol Biol. 2018 Feb;176:65-72. doi: 10.1016/j.jsbmb.2017.05.006. Epub 2017 May 18.
9
Sex steroids regulate skin pigmentation through nonclassical membrane-bound receptors.性类固醇通过非经典膜结合受体调节皮肤色素沉着。
Elife. 2016 Apr 26;5:e15104. doi: 10.7554/eLife.15104.
10
G protein-coupled estrogen receptor inhibits vascular prostanoid production and activity.G蛋白偶联雌激素受体抑制血管前列腺素的产生和活性。
J Endocrinol. 2015 Oct;227(1):61-9. doi: 10.1530/JOE-15-0257. Epub 2015 Aug 24.
本文引用的文献
1
A crowdsourcing evaluation of the NIH chemical probes.美国国立卫生研究院化学探针的众包评估。
Nat Chem Biol. 2009 Jul;5(7):441-7. doi: 10.1038/nchembio0709-441.
2
In vivo effects of a GPR30 antagonist.GPR30拮抗剂的体内效应。
Nat Chem Biol. 2009 Jun;5(6):421-7. doi: 10.1038/nchembio.168.
3
Chronic treatment with the G protein-coupled receptor 30 agonist G-1 decreases blood pressure in ovariectomized mRen2.Lewis rats.用G蛋白偶联受体30激动剂G-1进行长期治疗可降低去卵巢mRen2.Lewis大鼠的血压。
Endocrinology. 2009 Aug;150(8):3753-8. doi: 10.1210/en.2008-1664. Epub 2009 Apr 16.
4
Membrane estrogen receptor regulates experimental autoimmune encephalomyelitis through up-regulation of programmed death 1.膜雌激素受体通过上调程序性死亡蛋白1来调节实验性自身免疫性脑脊髓炎。
J Immunol. 2009 Mar 1;182(5):3294-303. doi: 10.4049/jimmunol.0803205.
5
Rapid action of oestrogen in luteinising hormone-releasing hormone neurones: the role of GPR30.雌激素在促黄体生成素释放激素神经元中的快速作用：GPR30的作用
J Neuroendocrinol. 2009 Mar;21(4):316-21. doi: 10.1111/j.1365-2826.2009.01839.x.
6
Regulatory role of G protein-coupled estrogen receptor for vascular function and obesity.G蛋白偶联雌激素受体对血管功能和肥胖的调节作用。
Circ Res. 2009 Feb 13;104(3):288-91. doi: 10.1161/CIRCRESAHA.108.190892. Epub 2009 Jan 29.
7
Involvement of G protein-coupled receptor 30 (GPR30) in rapid action of estrogen in primate LHRH neurons.G蛋白偶联受体30（GPR30）在雌激素对灵长类促黄体生成素释放激素（LHRH）神经元的快速作用中的参与。
Mol Endocrinol. 2009 Mar;23(3):349-59. doi: 10.1210/me.2008-0299. Epub 2009 Jan 8.
8
Expression of estrogen receptor GPR30 in the rat spinal cord and in autonomic and sensory ganglia.雌激素受体GPR30在大鼠脊髓、自主神经节和感觉神经节中的表达。
J Neurosci Res. 2009 May 15;87(7):1610-9. doi: 10.1002/jnr.21980.
9
Extra-nuclear estrogen receptor GPR30 regulates serotonin function in rat hypothalamus.核外雌激素受体GPR30调节大鼠下丘脑的5-羟色胺功能。
Neuroscience. 2009 Feb 18;158(4):1599-607. doi: 10.1016/j.neuroscience.2008.11.028. Epub 2008 Nov 21.
10
Involvement of estradiol-17beta and its membrane receptor, G protein coupled receptor 30 (GPR30) in regulation of oocyte maturation in zebrafish, Danio rario.17β-雌二醇及其膜受体G蛋白偶联受体30（GPR30）参与斑马鱼（Danio rario）卵母细胞成熟的调控。
Gen Comp Endocrinol. 2009 Mar;161(1):58-61. doi: 10.1016/j.ygcen.2008.10.003. Epub 2008 Oct 11.
Zotero 插件