1-甲基-1,4-二氢-2,3-喹喔啉二酮 | 20934-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 1-甲基-1,4-二氢-2,3-喹喔啉二酮
• 中文别名: 1,2,3,4-四氢-1-甲基-2,3-二氧代喹喔啉；4-甲基-1H-喹喔啉-2,3-二酮；1-甲基-1,4-二氢喹喔啉-2,3-二酮
• 英文名称: 1-methyl-1,4-dihydroquinoxaline-2,3-dione
• 英文别名: 1-methylquinoxaline-2,3(1H,4H)-dione；1,2,3,4-Tetrahydro-1-methyl-2,3-dioxo-chinoxalin；N-Methyl-1,4-dihydro-2,3-quinoxalinedione；4-methyl-1H-quinoxaline-2,3-dione
• CAS: 20934-51-4
• 化学式: C₉H₈N₂O₂
• mdl: MFCD11054015
• 分子量: 176.175
• InChiKey: ZJDLDFIDSAFPFG-UHFFFAOYSA-N

物化性质

• 熔点：
  281-283 °C
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险标志：
  GHS06
• 危险性描述：
  H301
• 危险性防范说明：
  P301 + P310
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  2811

反应信息

• 作为反应物：
  描述：

  1-甲基-1,4-二氢-2,3-喹喔啉二酮 在 吡啶 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 7.42h， 生成 Methyl 5-methyl-1,4-dioxo-[1,2,4]triazolo[4,3-a]quinoxaline-2-carboxylate
  参考文献：
  名称：

  1,2,4-Triazolo[4,3-a]quinoxaline-1,4-diones as antiallergic agents

  摘要：

  A series of new 1,4-dihydro-1,2,4-triazolo[4,3-]quinoxaline-1,4-diones has been prepared. These compounds were tested as inhibitors of antigen-induced release of histamine (AIR) in vitro from rat peritoneal mast cells (RMC) and as inhibitors of IgE-mediated rat passive cutaneous anaphylaxis (PCA). Most of this new class of antiallergic agents showed good activity in the RMC and PCA tests. The most potent compound, 2-acetyl-7-chloro-5-n-propyl-1,2,4-triazolo[4,3-a]quinoxaline-1,4-dione (1x), with an I50 value of 0.1 microM, is 30 times more potent than disodium cromoglycate (DSCG) in the RMC assay.

  DOI：

  10.1021/jm00381a016
• 作为产物：
  描述：

  N-甲基-2-硝基苯胺 在 sodium hydroxide 、 CaCl₂ 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 1-甲基-1,4-二氢-2,3-喹喔啉二酮
  参考文献：
  名称：

  Glycine receptor antagonists and the use thereof

  摘要：

  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。

  公开号：

  US05514680A1

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。
• K₂S₂O₈-catalyzed highly regioselective amidoalkylation of diverse N-heteroaromatics in water under visible light irradiation
  作者：Jiadi Zhou、Quanlei Ren、Ning Xu、Chaodong Wang、Shengjie Song、Zhi Chen、Jianjun Li

  DOI：10.1039/d1gc02107a

  日期：——

  N-heteroaromatics and γ-lactams/amides was developed. Quinoxalin-2(1H)-one, quinoline, isoquinoline, phthalazine, and benzothiazole reacted with γ-lactams/amides to give the corresponding C(sp2)–H amidoalkylation products in moderate to good yields with high regioselectivity. This visible-light-induced photocatalyst-free reaction was conducted in H2O at ambient temperature, which comply with the principles

  开发了 AK 2 S 2 O 8催化的多功能 C(sp 2 )–C(sp 3 ) 键与 N-杂芳烃和 γ-内酰胺/酰胺的形成。Quinoxalin-2(1 H )-one、喹啉、异喹啉、酞嗪和苯并噻唑与 γ-内酰胺/酰胺反应，以中等至良好的收率和高区域选择性得到相应的 C(sp 2 )-H 酰胺烷基化产物。这种可见光诱导的无光催化剂反应是在环境温度下在 H 2 O 中进行的，符合“绿色化学”的原则。新的 K 2 S 2 O 8 通过对照实验研究了催化机理。
• Direct C3-H carbamoylation of quinoxalin-2(1H)-ones with isocyanides enabled by selectfluor II under mild conditions
  作者：Jing Li、Jie Hu、Yao Xiao、Kun Yin、Wenyan Dan、Suhua Fan、Feng Jin、Hai Wu、Ronghua Zhang、Jian Li

  DOI：10.1016/j.tetlet.2021.153511

  日期：2022.1

  A F reagent-mediated direct C-H carbamoylation of quinoxalin-2(1H)-ones has been developed. Under room temperature, a variety of isocyanides are employed to couple well with quinoxalin-2(1H)-ones affording 42 examples including 30 new compounds. This metal-free mild strategy tolerates a wide range of functional groups and shows environmental friendliness and practicality.

  已经开发了AF 试剂介导的 quinoxalin-2( 1H )-ones 的直接 CH 氨基甲酰化。在室温下，使用多种异氰化物与 quinoxalin-2( 1H )-ones很好地偶联，得到 42 个例子，包括 30 个新化合物。这种不含金属的温和策略可以容忍广泛的官能团，并显示出环境友好性和实用性。
• DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
  申请人：Chiesi Farmaceutici S.p.A.

  公开号：US20130102576A1

  公开（公告）日：2013-04-25

  Compounds, pyridine N-oxides, and pharmaceutically acceptable salts of formula (I) are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme and for preventing and/or treating diseases of the respiratory tract characterized by airway obstruction, such as asthma or COPD.

  化合物，吡啶N-氧化物和具有以下结构的药学上可接受的盐（I）的盐对于抑制磷酸二酯酶4（PDE4）酶并预防和/或治疗呼吸道疾病，其特征是气道阻塞，如哮喘或COPD，是有用的。
• Tricyclic heterocyclic compounds as psychopharmaceuticals
  申请人：A/S Ferrosan

  公开号：US04873244A1

  公开（公告）日：1989-10-10

  New heterocyclic compounds having the general formula ##STR1## wherein ##STR2## CO.sub.2 R' or CONR'R", wherein R' and R" independently are C.sub.1-6 -alkyl, C.sub.3-7 -cycloalkyl or C.sub.1-6 -alkoxymethyl; --A-- is --C(.dbd.O)--NR'"--, --NR'"--C(.dbd.O)--, or ##STR3## wherein R'" is C.sub.1-6 -alkyl; X is C or N; and R.sup.4 is hydrogen, halogen, CN, C.sub.1-6 -alkyl, C.sub.1-6 -alkynyl, trimethylsilyl-C.sub.1-6 -alkynyl, aryloxy which may be substituted with halogen, aralkoxy, C.sub.3-7 -cycloalkoxy which may be substituted with one or more C.sub.1-6 -alkyl groups, or NR""R'"", wherein R"" and R'"" independently are C.sub.1-6 -alkoxy or together with the nitrogen atom form a 3-7 membered heterocyclic ring. The compounds are useful in psychopharmaceutical preparations as anticonvulsants, anxiolytics, hypnotics, and nootropics.

  新的杂环化合物具有一般公式##STR1##其中##STR2## CO.sub.2 R'或CONR'R"，其中R'和R"独立地为C.sub.1-6-烷基，C.sub.3-7-环烷基或C.sub.1-6-烷氧甲基；--A--为--C(.dbd.O)--NR'"--，--NR'"--C(.dbd.O)--，或##STR3##其中R'"为C.sub.1-6-烷基；X为C或N；R.sup.4为氢，卤素，CN，C.sub.1-6-烷基，C.sub.1-6-炔基，三甲基硅基-C.sub.1-6-炔基，可能被卤素取代的芳基氧，芳基氧基，C.sub.3-7-环烷氧，可能被一个或多个C.sub.1-6-烷基基团取代的NR""R'"，其中R""和R'""独立地为C.sub.1-6-烷氧基，或者与氮原子一起形成3-7成员杂环环。这些化合物在精神药物制剂中作为抗癫痫药、抗焦虑药、催眠药和脑功能增强剂中很有用。

表征谱图