4-Nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate (BioDeep_00001875895)

   


代谢物信息卡片


4-Nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate

化学式: C27H24N2O9 (520.1481734)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CN(CCC1C(C2=CC3=C(C=C2)OCO3)(C4=CC5=C(C=C4)OCO5)O)C(=O)OC6=CC=C(C=C6)[N+](=O)[O-]
InChI: InChI=1S/C27H24N2O9/c30-26(38-21-5-3-20(4-6-21)29(32)33)28-11-9-17(10-12-28)27(31,18-1-7-22-24(13-18)36-15-34-22)19-2-8-23-25(14-19)37-16-35-23/h1-8,13-14,17,31H,9-12,15-16H2

描述信息

JZL 184 is a potent, selective and irreversible MAGL inhibitor that blocks 2-Arachidonoylglycerol (2-AG) hydrolysis in brain membranes (IC50 of 8 nM). JZL 184 displays >300-fold selectivity for MAGL over FAAH[1][2].

同义名列表

2 个代谢物同义名

4-Nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate; JZL 184



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5 个数据库交叉引用编号

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文献列表

  • Melike Demir Çaltekin, Mahmud Mustafa Özkut, İbrahim Çaltekin, Emin Kaymak, Murat Çakır, Mustafa Kara, Ethem Serdar Yalvaç. The protective effect of JZL184 on ovarian ischemia reperfusion injury and ovarian reserve in rats. The journal of obstetrics and gynaecology research. 2021 Aug; 47(8):2692-2704. doi: 10.1111/jog.14859. [PMID: 34008304]
  • Emily Kabeiseman, Riley Paulsen, Brian D Burrell. Characterization of a monoacylglycerol lipase in the medicinal leech, Hirudo verbana. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2020 Jun; 243-244(?):110433. doi: 10.1016/j.cbpb.2020.110433. [PMID: 32205202]
  • Jing Wang, Xiaohua Zhang, Chongmei Yang, Shulei Zhao. Effect of monoacylglycerol lipase inhibition on intestinal permeability in chronic stress model. Biochemical and biophysical research communications. 2020 05; 525(4):962-967. doi: 10.1016/j.bbrc.2020.02.173. [PMID: 32173532]
  • Matteo Tardelli, Francesca V Bruschi, Claudia D Fuchs, Thierry Claudel, Nicole Auer, Victoria Kunczer, Maximilian Baumgartner, Onne A H O Ronda, Henk Jan Verkade, Tatjana Stojakovic, Hubert Scharnagl, Aida Habib, Robert Zimmermann, Sophie Lotersztajn, Michael Trauner. Monoacylglycerol Lipase Inhibition Protects From Liver Injury in Mouse Models of Sclerosing Cholangitis. Hepatology (Baltimore, Md.). 2020 05; 71(5):1750-1765. doi: 10.1002/hep.30929. [PMID: 31505038]
  • Xin Li, Shuhong Gao, Wenzhi Li, Zhiming Liu, Zhengzheng Shi, Chunping Qiu, Jie Jiang. Effect of monoacylglycerol lipase on the tumor growth in endometrial cancer. The journal of obstetrics and gynaecology research. 2019 Oct; 45(10):2043-2054. doi: 10.1111/jog.14070. [PMID: 31357249]
  • Alice L Chen, Kenneth M Lum, Pablo Lara-Gonzalez, Daisuke Ogasawara, Armand B Cognetta, Alan To, William H Parsons, Gabriel M Simon, Arshad Desai, Michael Petrascheck, Liron Bar-Peled, Benjamin F Cravatt. Pharmacological convergence reveals a lipid pathway that regulates C. elegans lifespan. Nature chemical biology. 2019 05; 15(5):453-462. doi: 10.1038/s41589-019-0243-4. [PMID: 30911178]
  • Kristen R Trexler, Sara R Nass, Molly S Crowe, Joshua D Gross, Margaret S Jones, Austin W McKitrick, David P Siderovski, Steven G Kinsey. Novel behavioral assays of spontaneous and precipitated THC withdrawal in mice. Drug and alcohol dependence. 2018 Oct; 191(?):14-24. doi: 10.1016/j.drugalcdep.2018.05.029. [PMID: 30071445]
  • Gaurav Bedse, Rebecca J Bluett, Toni A Patrick, Nicole K Romness, Andrew D Gaulden, Philip J Kingsley, Niels Plath, Lawrence J Marnett, Sachin Patel. Therapeutic endocannabinoid augmentation for mood and anxiety disorders: comparative profiling of FAAH, MAGL and dual inhibitors. Translational psychiatry. 2018 04; 8(1):92. doi: 10.1038/s41398-018-0141-7. [PMID: 29695817]
  • Cristina da Costa Oliveira, Clarice de Carvalho Veloso, Renata Cristina Mendes Ferreira, Gisele Avelar Lage, Lúcia Pinheiro Santos Pimenta, Igor Dimitri Gama Duarte, Thiago Roberto Lima Romero, Andrea de Castro Perez. Peltatoside Isolated from Annona crassiflora Induces Peripheral Antinociception by Activation of the Cannabinoid System. Planta medica. 2017 Feb; 83(3-04):261-267. doi: 10.1055/s-0042-113386. [PMID: 27574895]
  • Junyong Zhang, Zuojin Liu, Zhengrong Lian, Rui Liao, Yi Chen, Yi Qin, Jinlong Wang, Qing Jiang, Xiaobo Wang, Jianping Gong. Monoacylglycerol Lipase: A Novel Potential Therapeutic Target and Prognostic Indicator for Hepatocellular Carcinoma. Scientific reports. 2016 10; 6(?):35784. doi: 10.1038/srep35784. [PMID: 27767105]
  • Sally Miller, Emma Leishman, Sherry Shujung Hu, Alhasan Elghouche, Laura Daily, Natalia Murataeva, Heather Bradshaw, Alex Straiker. Harnessing the Endocannabinoid 2-Arachidonoylglycerol to Lower Intraocular Pressure in a Murine Model. Investigative ophthalmology & visual science. 2016 Jun; 57(7):3287-96. doi: 10.1167/iovs.16-19356. [PMID: 27333182]
  • James Lim, Miki Igarashi, Kwang-Mook Jung, Stefania Butini, Giuseppe Campiani, Daniele Piomelli. Endocannabinoid Modulation of Predator Stress-Induced Long-Term Anxiety in Rats. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2016 Apr; 41(5):1329-39. doi: 10.1038/npp.2015.284. [PMID: 26361059]
  • Charles A Berdan, Karel A Erion, Nathan E Burritt, Barbara E Corkey, Jude T Deeney. Inhibition of Monoacylglycerol Lipase Activity Decreases Glucose-Stimulated Insulin Secretion in INS-1 (832/13) Cells and Rat Islets. PloS one. 2016; 11(2):e0149008. doi: 10.1371/journal.pone.0149008. [PMID: 26867016]
  • Takahiro Shimizu, Kenjiro Tanaka, Kumiko Nakamura, Keisuke Taniuchi, Toshio Yawata, Youichirou Higashi, Tetsuya Ueba, Fotios Dimitriadis, Shogo Shimizu, Kunihiko Yokotani, Motoaki Saito. Possible involvement of brain prostaglandin E2 and prostanoid EP3 receptors in prostaglandin E2 glycerol ester-induced activation of central sympathetic outflow in the rat. Neuropharmacology. 2014 Jul; 82(?):19-27. doi: 10.1016/j.neuropharm.2014.03.005. [PMID: 24657150]
  • Giovane Galdino, Thiago R L Romero, José Felipe P Silva, Daniele C Aguiar, Ana Maria de Paula, Jader S Cruz, Cosimo Parrella, Fabiana Piscitelli, Igor D Duarte, Vincenzo Di Marzo, Andrea C Perez. The endocannabinoid system mediates aerobic exercise-induced antinociception in rats. Neuropharmacology. 2014 Feb; 77(?):313-24. doi: 10.1016/j.neuropharm.2013.09.022. [PMID: 24148812]
  • D M Kerr, B Harhen, B N Okine, L J Egan, D P Finn, M Roche. The monoacylglycerol lipase inhibitor JZL184 attenuates LPS-induced increases in cytokine expression in the rat frontal cortex and plasma: differential mechanisms of action. British journal of pharmacology. 2013 Jun; 169(4):808-19. doi: 10.1111/j.1476-5381.2012.02237.x. [PMID: 23043675]
  • Mano Aliczki, Dora Zelena, Eva Mikics, Zoltan K Varga, Otto Pinter, Nikoletta Venczkone Bakos, Janos Varga, Jozsef Haller. Monoacylglycerol lipase inhibition-induced changes in plasma corticosterone levels, anxiety and locomotor activity in male CD1 mice. Hormones and behavior. 2013 May; 63(5):752-8. doi: 10.1016/j.yhbeh.2013.03.017. [PMID: 23578952]
  • Zongxian Cao, Melinda M Mulvihill, Partha Mukhopadhyay, Huan Xu, Katalin Erdélyi, Enkui Hao, Eileen Holovac, György Haskó, Benjamin F Cravatt, Daniel K Nomura, Pál Pacher. Monoacylglycerol lipase controls endocannabinoid and eicosanoid signaling and hepatic injury in mice. Gastroenterology. 2013 Apr; 144(4):808-817.e15. doi: 10.1053/j.gastro.2012.12.028. [PMID: 23295443]
  • Josée Guindon, Yvonne Lai, Sara M Takacs, Heather B Bradshaw, Andrea G Hohmann. Alterations in endocannabinoid tone following chemotherapy-induced peripheral neuropathy: effects of endocannabinoid deactivation inhibitors targeting fatty-acid amide hydrolase and monoacylglycerol lipase in comparison to reference analgesics following cisplatin treatment. Pharmacological research. 2013 Jan; 67(1):94-109. doi: 10.1016/j.phrs.2012.10.013. [PMID: 23127915]
  • Takahiro Shimizu, Kenjiro Tanaka, Kunihiko Yokotani. Stimulatory and inhibitory roles of brain 2-arachidonoylglycerol in bombesin-induced central activation of adrenomedullary outflow in rats. Journal of pharmacological sciences. 2013; 121(2):157-71. doi: 10.1254/jphs.12208fp. [PMID: 23386378]
  • J Allen Crow, Victoria Bittles, Abdolsamad Borazjani, Philip M Potter, Matthew K Ross. Covalent inhibition of recombinant human carboxylesterase 1 and 2 and monoacylglycerol lipase by the carbamates JZL184 and URB597. Biochemical pharmacology. 2012 Nov; 84(9):1215-22. doi: 10.1016/j.bcp.2012.08.017. [PMID: 22943979]
  • Takahiro Shimizu, Kenjiro Tanaka, Kumiko Nakamura, Keisuke Taniuchi, Kunihiko Yokotani. Brain phospholipase C, diacylglycerol lipase and monoacylglycerol lipase are involved in (±)-epibatidine-induced activation of central adrenomedullary outflow in rats. European journal of pharmacology. 2012 Sep; 691(1-3):93-102. doi: 10.1016/j.ejphar.2012.07.017. [PMID: 22796670]
  • Meghan Johnston, Shachi R Bhatt, Surina Sikka, Richard W Mercier, Jay M West, Alexandros Makriyannis, S John Gatley, Richard I Duclos. Assay and inhibition of diacylglycerol lipase activity. Bioorganic & medicinal chemistry letters. 2012 Jul; 22(14):4585-92. doi: 10.1016/j.bmcl.2012.05.101. [PMID: 22738638]
  • Takahiro Shimizu, Lianyi Lu, Kunihiko Yokotani. Endogenously generated 2-arachidonoylglycerol plays an inhibitory role in bombesin-induced activation of central adrenomedullary outflow in rats. European journal of pharmacology. 2011 May; 658(2-3):123-31. doi: 10.1016/j.ejphar.2011.02.023. [PMID: 21371452]
  • Shuqi Xie, Abdolsamad Borazjani, M Jason Hatfield, Carol C Edwards, Philip M Potter, Matthew K Ross. Inactivation of lipid glyceryl ester metabolism in human THP1 monocytes/macrophages by activated organophosphorus insecticides: role of carboxylesterases 1 and 2. Chemical research in toxicology. 2010 Dec; 23(12):1890-904. doi: 10.1021/tx1002194. [PMID: 21049984]