噻氮卓并[3,4-a]异喹啉的首次合成、一种简便的二氮卓并[3,4-a]异喹啉新合成路线及其对多巴胺和σ受体亲和力的评估。
First synthesis of thiazepino[3,4-a]isoquinolines, a facile new synthetic route to diazepino[3,4-a]isoquinolines and assessment of their dopamine and σ receptor affinities.
作者信息
Cordone Pierpaolo, Namballa Hari Krishna, Harding Wayne Wesley
机构信息
Department of Chemistry, Hunter College, City University of New York, New York, New York.
Ph.D. Program in Biochemistry, CUNY Graduate Center, New York, New York.
出版信息
J Heterocycl Chem. 2020 Oct;57(10):3709-3713. doi: 10.1002/jhet.4086. Epub 2020 Apr 4.
Abstract
Heterocycles that bear the novel 5,6,14,14a-tetrahydro-8H-benzo[6,7][1,4] thiazepino[3,4-a]isoquinoline and the 5,6,14,14a-tetrahydro-8H-13l2-benzo [6,7][1,4]diazepino[3,4-a]isoquinoline frameworks were synthesized in a facile manner. These tetrahydroprotoberberine (THPB)-inspired scaffolds demonstrate selective affinity for the σR in contrast to the naturally occurring THPB congeners that show DR and σR selectivity.
摘要
带有新型5,6,14,14a-四氢-8H-苯并[6,7][1,4]噻氮杂卓并[3,4-a]异喹啉和5,6,14,14a-四氢-8H-13l2-苯并[6,7][1,4]二氮杂卓并[3,4-a]异喹啉骨架的杂环化合物以简便的方式合成。与显示出多巴胺受体（DR）和σ受体（σR）选择性的天然存在的四氢原小檗碱（THPB）同系物相比，这些受四氢原小檗碱启发的支架对σR表现出选择性亲和力。
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本文引用的文献
1
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J Nucl Med. 2020 May;61(5):665-670. doi: 10.2967/jnumed.119.232363. Epub 2019 Dec 13.
2
The Roles of Intracellular Chaperone Proteins, Sigma Receptors, in Parkinson's Disease (PD) and Major Depressive Disorder (MDD).细胞内伴侣蛋白西格玛受体在帕金森病（PD）和重度抑郁症（MDD）中的作用。
Front Pharmacol. 2019 May 21;10:528. doi: 10.3389/fphar.2019.00528. eCollection 2019.
3
Sigma-2 receptor: past, present and perspectives on multiple therapeutic exploitations.Sigma-2 受体：在多种治疗开发方面的过去、现在和展望。
Future Med Chem. 2018 Aug 1;10(16):1997-2018. doi: 10.4155/fmc-2018-0072. Epub 2018 Jul 3.
4
(-)-Stepholidine reduces cue-induced reinstatement of cocaine seeking and cocaine self-administration in rats.(-)-石杉碱甲可减少大鼠线索诱导的可卡因觅药行为复发和可卡因自身给药。
Drug Alcohol Depend. 2018 Aug 1;189:49-54. doi: 10.1016/j.drugalcdep.2018.04.030. Epub 2018 May 31.
5
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ACS Chem Neurosci. 2018 Jun 20;9(6):1327-1337. doi: 10.1021/acschemneuro.7b00510. Epub 2018 Apr 6.
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Int Rev Neurobiol. 2017;135:279-295. doi: 10.1016/bs.irn.2017.02.013. Epub 2017 Mar 25.
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