CAS: 153504-81-5; 6,7-Dichloro-5-Nitroquinoxaline-2,3(1H,4H)-Dione

该化合物是一个化学化合物,主要针对其潜在的治疗应用进行了研究,被归类为N-甲基D-partate(NMDA)受体的选择性敌者,该受体在合成塑料和记忆功能方面起着关键作用.该受体表现出...

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CAS号25983-13-5 6,7-二氯喹啉-2,3-(1... | CAS号153505-40-9 6,7-Dichloro-3,... | CAS号78470-95-8 2-羟基-6,7-二氯喹喔啉 | CAS号5348-42-5 4,5-二氯-1,2-苯二胺 | CAS号21641-42-9 5,6-dichloro-2,... | CAS号95-92-1 草酸二乙酯 | CAS号276238-86-9 4,5-Dichloro-3-... | CAS号178619-89-1 6,7-DICHLOOR-2,...

合成工艺路线路线简述

  • 合成目标产物 Licostinel 主要起始原料 6,7-Dichloro-1,4-Dihydro-2,3-Quinoxalinedione
  • (文献来源)合成步骤主要原料 6,7-Dichloro-1,4-Dihydro-2,3-Quinoxalinedione
📜6,7-Dichloro-3,4-Dihydroquinoxalin-2(1H)-One置于硝酸体系中,用 三氟乙酸 用作溶剂,化学反应 72.0H,以91%的收率获得利可替奈
参考文献:Regiospecific Oxidative Nitration Of 3,4-Dihydro-6,7-Disubstituted Quinoxaline-2(1H)-Ones Gives 1,4-Dihydro-5-Nitro-6,7-Disubstituted Quinoxaline-2,3-Diones,Potent Antagonists At The Nmda/glycine Site
标题:Regiospecific Oxidative Nitration Of 3,4-Dihydro-6,7-Disubstituted Quinoxaline-2(1H)-Ones Gives 1,4-Dihydro-5-Nitro-6,7-Disubstituted Quinoxaline-2,3-Diones,Potent Antagonists At The Nmda/glycine Site
摘要:The Regiospecific Oxidative Nitration Of 3,4-Dihydro-6,7-Disubstituted Quinoxalin-2(1H)-Ones (15A-H,20) Utilizing Fuming Nitric Acid In Tfa Gave 1,4-Dihydro-5-Nitro-6,7-Disubstituted Quinoxaline-2,3-Diones (6A-I),Respectively,In Good Yields. Compounds 15A-H Were Prepared From Commercially Available 1-Halo-3,4-Disubstituted Benzenes 12A-H In Three Steps. These Were Nitration,Nucleophilic Substitution Of The Halogen Ortho To The Nitro Group With Sodium Glycinate,And Finally,Reduction Of The Nitro Group And Concomitant Cyclization,Compound 20 Was Prepared From 16 By A Different Route Involving Alkylation Of Substituted O-Nitroaniline 18. The Final Oxidative Nitration Yields A Single,Predictable Nitro Isomer And Is A Significant Improvement Over The Direct Nitration Of 6,7-Disubstituted Quinoxaline-2,3-Diones.
Doi:10.1021/jo00123A020

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专利信息


专利号:US-5708168-A
优先权日:1994-11-16
标 题 :Azepine compounds
发明人:KEANA JOHN F W; GUZIKOWSKI ANTHONY P; NOGALES DANIEL F; CAI SUI XIONG
权利人:OREGON STATE; ACEA PHARM INC
摘要:Disclosed are methods of preparing azepines by a multistep synthesis including a Diels-Alder reaction. Also disclosed are methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, inducing anesthesia and treating or preventing opiate tolerance are disclosed by administering to an animal in need of such treatment an azepine which has high binding to the NMDA glycine site.

专利号:PT-1883451-E
优先权日:2005-04-13
标 题 :SUBSTITUTED INDOOR COMPOUNDS WITH INHIBITORY ACTIVITY OF NITRIC OXIDE SYNTHESIS (NOS)

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主要参考文献


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合成参考文献


参考文献:10.1007/s004010051054
摘要:Kornhuber J, Jellinger K, Wiltfang J, Leblhuber F, Riederer P. The N-methyl-D-aspartate receptor channel blocker amantadine does not cause histopathological alterations in human brain tissue. Acta Neuropathol. 1999 Jul;98(1):85–90. doi: 10.1007/s004010051054.
参考文献:10.1007/bf02975090
摘要:Hwang KJ, Lee TS, Kim KW, Kim BT, Lee CM, Park EY, Woo RS. 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b] pyrimidine derivatives: synthesis and their biological evaluation for the glycine site acting on the N-methyl-D-aspartate (NMDA) receptor. Arch Pharm Res. 2001 Aug;24(4):270–5. doi: 10.1007/bf02975090.
参考文献:10.1016/s0006-8993(96)01017-7
摘要:Lutfy K, Weber E. Attenuation of nociceptive responses by ACEA-1021, a competitive NMDA receptor/glycine site antagonist, in the mice. Brain Res. 1996 Dec 16;743(1-2):17–23. doi: 10.1016/s0006-8993(96)01017-7.
参考文献:10.1016/s0006-8993(96)01064-5
摘要:Hawkinson JE, Huber KR, Sahota PS, Han Hsu H, Weber E, Whitehouse MJ. The N-methyl-D-aspartate (NMDA) receptor glycine site antagonist ACEA 1021 does not produce pathological changes in rat brain. Brain Res. 1997 Jan 09;744(2):227–34. doi: 10.1016/s0006-8993(96)01064-5.
参考文献:10.1097/00004647-199702000-00005
摘要:Takaoka S, Bart RD, Pearlstein R, Brinkhous A, Warner DS. Neuroprotective effect of NMDA receptor glycine recognition site antagonism persists when brain temperature is controlled. J Cereb Blood Flow Metab. 1997 Feb;17(2):161–7. doi: 10.1097/00004647-199702000-00005.
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