6,7-dichloro-1-ethoxycarbonylmethylquinoxaline-2(1H)-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6,7-dichloro-1-ethoxycarbonylmethylquinoxaline-2(1H)-one
• 英文别名: 6,7-dichloro-1-ethoxycarbonylmethylquinoxalin-2(1H)-one；ethyl 2-(6,7-dichloro-2-oxoquinoxalin-1-yl)acetate
• 化学式: C₁₂H₁₀Cl₂N₂O₃
• 分子量: 301.129
• InChiKey: PJXPMTUCTFZDOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,7-dichloro-1-ethoxycarbonylmethylquinoxaline-2(1H)-one 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到C₁₀H₆Cl₂N₂O₃
  参考文献：
  名称：

  Development of potent and selective small-molecule human Urotensin-II antagonists

  摘要：

  This work describes the development of potent and selective human Urotensin-II receptor antagonists starting from lead compound 1, (3,4-dichlorophenyl) methyl{2-oxo-2-[3-phenyl-2-(1-pyrrolidinylmethyl)1-piperidinyl]ethyl}amine. Several problems relating to oral bioavailability, cytochrome P450 inhibition, and off-target activity at the kappa opioid receptor and cardiac sodium channel were addressed during lead development. hUT binding affinity relative to compound 1 was improved by more than 40-fold in some analogs, and a structural modi. cation was identified which significantly attenuated both off-target activities. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.027
• 作为产物：
  描述：

  diethyl 2,2'-((4,5-dichloro-1,2-phenylene)bis(azanediyl))diacetate 反应 12.0h， 以228 mg的产率得到6,7-dichloro-1-ethoxycarbonylmethylquinoxaline-2(1H)-one
  参考文献：
  名称：

  O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources

  摘要：

  氯化四苯基卟啉铁(III)Fe(TPP)Cl 可高效催化 2-苯基重氮乙酸甲酯衍生的碳烯插入脂肪醇和芳香醇的 O-H 键，产率一般在 80% 以上。虽然类似的 N-H 插入反应在室温下就能迅速完成，但 O-H 插入反应速度较慢，需要在使用 1.0 mol.% 催化剂的情况下在回流二氯甲烷中加热约 8 小时。在用重氮试剂处理 1,2-二胺和 1,2-醇胺以得到哌嗪酮和吗啉酮以及相关类似物（如喹喔啉酮和苯并恶嗪-2-酮）时，还发现 Fe(TPP)Cl 对串联 N-H 插入/环化反应非常有效。这种方法为合成这类杂环化合物提供了一条新的一步法途径。

  DOI：

  10.1142/s1088424610001982

文献信息

• Glycine receptor antagonists and the use thereof
  申请人：The State of Oregon, acting by and through The Oregon State Board of

  公开号：US05514680A1

  公开（公告）日：1996-05-07

  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 psychosis are disclosed by administering to an animal in need of such treatment a compound having high affinity for the glycine binding site, lacking PCP side effects and which crosses the blood brain barrier of the animal. Also disclosed are novel 1,4-dihydroquinoxaline-2,3-diones, and pharmaceutical compositions thereof. Also disclosed are highly soluble ammonium salts of 1,4-dihydroquinoxaline-2,3-diones.

  治疗或预防与中风、缺血、中枢神经系统创伤、低血糖和手术相关的神经元损失的方法，以及治疗包括阿尔茨海默病、肌萎缩侧索硬化、亨廷顿病和唐氏综合症在内的神经退行性疾病，治疗或预防兴奋性氨基酸过度活跃的副作用，以及治疗焦虑、慢性疼痛、癫痫、诱导麻醉和治疗精神病的方法，通过向需要此类治疗的动物施用一种对甘氨酸结合位点具有高亲和力、无PCP副作用且能穿过动物血脑屏障的化合物来进行披露。还披露了新型的1,4-二氢喹诺酮-2,3-二酮，及其药物组合物。还披露了1,4-二氢喹诺酮-2,3-二酮的高度可溶性铵盐。
• Silver-catalyzed decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo-carboxylic acids
  作者：Xiaobao Zeng、Chulong Liu、Xingyong Wang、Jianlan Zhang、Xinyan Wang、Yuefei Hu

  DOI：10.1039/c7ob02187a

  日期：——

  C–H bond acylation of quinoxalin-2(1H)-ones. In this method, α-oxo-carboxylic acids served as efficient acylating reagents to in situ generate the required active acyl radical. Its excellent chemoselectivity allowed the molecular diversity of 3-acyl quinoxalin-2(1H)-ones to be achieved by convenient functionalizations of both N1- and C3-positions.

  开发了一种新型的银催化的α-氧代羧酸脱羧酰化反应，通过喹喔啉-2（1 H）-的直接C–H键酰化反应合成了各种3-酰基喹喔啉-2（1 H）-。那些。在这种方法中，α-氧代羧酸可作为有效的酰化试剂，以原位生成所需的活性酰基。它具有出色的化学选择性，可通过N1-和C3位置的便捷官能化来实现3-酰基喹喔啉-2（1 H）-ones的分子多样性。
• Quinoxaline-2,3-dione compounds and their preparation and use
  申请人：Novo Nordisk A/S

  公开号：US05166155A1

  公开（公告）日：1992-11-24

  1-carboxyalkylquinoxaline-2,3(1H,4H)-dione compounds or tautomeric forms thereof of the formula ##STR1## wherein R represents hydrogen, C.sub.1-6 -alkyl, including branched chains, or aralkyl and n represents the number from 0 to 5; R.sup.4 represents hydrogen or hydroxy; R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently represent hydrogen, nitro, halogen, alkoxy, aryloxy, aralkoxy, C.sub.1-6 -alkyl including branched chains, or aryl; R.sup.9 represents hydrogen, lower alkyl, or aryl; R.sup.10 represents hydrogen, or alkyl. The compounds are useful in the treatment of neurological and psychiatric diseases.

  1-羧基烷基喹喔啉-2,3(1H,4H)-二酮化合物或其互变异构体，其化学式为##STR1##其中，R表示氢、C.sub.1-6-烷基（包括支链）或芳基烷基，n表示0到5的数字；R.sup.4表示氢或羟基；R.sup.5、R.sup.6、R.sup.7和R.sup.8独立地表示氢、硝基、卤素、烷氧基、芳氧基、芳基烷氧基、C.sub.1-6-烷基（包括支链）或芳基；R.sup.9表示氢、低碳基或芳基；R.sup.10表示氢或烷基。这些化合物可用于治疗神经和精神疾病。
• QUINOXALINE COMPOUNDS AND THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0520024B1

  公开（公告）日：1996-06-19
• GLYCINE RECEPTOR ANTAGONISTS AND THE USE THEREOF
  申请人：The Regents of the University of California

  公开号：EP0647137B1

  公开（公告）日：2008-08-13