1,3-Dimethyl-6-phenylpyrazino<2,3-d>pyrimidine-2,4(1H,3H)-dione | 25477-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1,3-Dimethyl-6-phenylpyrazino<2,3-d>pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-dimethyl-2,4-dioxo-6-phenyl-1,2,3,4-tetrahydropteridine；1,3-dimethyl-6-phenyl-1H-pteridine-2,4-dione；6-phenyl-1,3-dimethyllumazine；1,3-dimethyl-6-phenyl-1H-pteridine-2,4-dione；1,3-Dimethyl-6-phenyl-1H-pteridin-2,4-dion；1,3-Dimethyl-6-phenyl-2,4(1H,3H)-pteridindion；1,3-Dimethyl-6-phenylpteridine-2,4-dione
• CAS: 25477-76-3
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: DKIVATKWMWLPJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-6-phenylpyrazino<2,3-d>pyrimidine-2,4(1H,3H)-dione 在 氢氧化钾 作用下， 生成 3-methylamino-6-phenyl-pyrazine-2-carboxylic acid methylamide
  参考文献：
  名称：

  Determination of Triazines in Water Samples by High-Performance Liquid Chromatography with Diode-Array Detection

  摘要：

  三嗪类除草剂广泛使用，可在环境中以痕量水平被检测到。分析前需要一个预浓集步骤。本研究中，比较了炭质和聚合物吸附剂与C18在固相萃取水中西玛津、阿特拉津和扑灭津的效果，以便通过使用光电二极管阵列检测的高性能液相色谱法定量它们的含量。

  DOI：

  10.1093/chromsci/40.9.523
• 作为产物：
  描述：

  1,3-二甲基-6-亚氨基-5-异亚硝基尿嘧啶 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1,3-Dimethyl-6-phenylpyrazino<2,3-d>pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Igarashi, Mamoru; Tada, Masaru, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 807 - 810

  摘要：

  DOI：

文献信息

• Immunosuppressive effects of pteridine derivatives
  申请人：——

  公开号：US20030236255A1

  公开（公告）日：2003-12-25

  Novel poly-substituted pteridinediones (lumazines), and mono- or polysubstituted 2-thiolumazines, 4-thiolumazines or 2,4-dithiolumazines, having disclosed substituents in positions 1, 3, 6 and 7 of the pteridine ring, and pharmaceutically acceptable salts thereof, are useful as biologically active ingredients in preparing pharmaceutical compositions especially for the treatment or prevention of a CNS disorder, a cell proliferative disorder, a viral infection, an immune or auto-immune disorder or a transplant rejection. Combinations of the pteridine derivatives of the invention with an immunosuppressant or immunomodulator drug, an antineoplastic drug or an antiviral agent, providing potential synergistic effects, are also disclosed.

  新型多取代的喹啉二酮（卢马嗪），以及单取代或多取代的2-硫代卢马嗪，4-硫代卢马嗪或2,4-二硫代卢马嗪，在喹啉环的1、3、6和7位上具有已披露的取代基，并且其药学上可接受的盐，在制备药物组合物中作为生物活性成分特别用于治疗或预防中枢神经系统疾病、细胞增殖障碍、病毒感染、免疫或自身免疫障碍或移植排斥。本发明的喹啉衍生物与免疫抑制剂或免疫调节剂药物、抗肿瘤药物或抗病毒药物的组合，提供潜在的协同效应。
• Synthesis, DNA Binding and Antiviral Activity of New Uracil, Xanthine, and Pteridine Derivatives
  作者：Osama I. El-Sabbagh、Mohamed E. El-Sadek、Samar El-Kalyoubi、Ibrahim Ismail

  DOI：10.1002/ardp.200600149

  日期：2007.1

  Some new 6‐amino‐1,3‐dimethyl‐5‐(substituted methylidene)aminouracils were synthesized. Most of them were cyclized with triethyl orthoformate as a one‐carbon source to afford 1,3‐dimethyl‐6‐substituted pteridine derivatives. Certain uracils gave xanthine instead of the expected pteridine derivatives upon using another one‐carbon source such as triethyl orthoacetate or triethyl orthobenzoate. The nucleic

  合成了一些新的6-氨基-1,3-二甲基-5-（取代亚甲基）氨基尿嘧啶。它们中的大多数与原甲酸三乙酯作为单碳源环化，得到 1,3-二甲基-6-取代的蝶啶衍生物。某些尿嘧啶在使用另一种单碳源（如原乙酸三乙酯或原苯甲酸三乙酯）时产生黄嘌呤而不是预期的蝶啶衍生物。核酸结合试验表明，与仅对 DNA 具有亲和力的阿昔洛韦相反，一些新化合物显示出高亲和力、螯合和核酸片段化，无论是 DNA 还是 RNA。这些新型化合物的抗病毒活性表明，化合物 2e 和 2f 分别将 Vero 细胞培养物中小反刍兽疫病毒 (PPRV) 的细胞致病性降低了 60% 和 50%。
• Facile Synthesis of 6-Aryl-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine-2,4(1H,3H)-diones
  作者：Shahriyar Taghavi-Moghadam、Rüdiger Stumpf、Helmut Fischer、Wolfgang Pfleiderer

  DOI：10.1135/cccc19990313

  日期：——

  A facile procedure for the preparation of 6-aryl-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine2,4(1H,3H)-diones 8, 9 from 6-amino-5-arylideneamino-1,3-dimethyluracils 1, 2 and triethyl orthoacetate (3) in a two-step reaction via 6-aryl-8-ethoxy-6,7-dihydro-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine-2,4(1H,3H)-diones 6, 7 is described. Condensation of 1 with diethoxymethyl acetate (10) resulted in the formation of (1,3-dimethyl-2,6-(1H,3H)-dioxopurin-7-yl)(phenyl)methyl acetate (11) and a small amount of 1,3-dimethyl-6-phenylpyrazino[2,3-d]pyrimidine-2,4(1H,3H)-dione (12). The structures of 6 and 11 were unambiguously confirmed by single-crystal X-ray diffraction analysis.

  使用两步反应通过6-氨基-5-芳基亚甲基氨基-1,3-二甲基尿嘧啶1,2和三乙基正酯（3），制备6-芳基-1,3-二甲基-5H-嘧啶并[4,5-b][1,4]二氮杂环己烷-2,4（1H，3H）-二酮8、9。通过将1和二乙氧甲基乙酸酯（10）缩合，形成（1,3-二甲基-2,6-(1H,3H)-二氧代嘌呤-7-基）（苯基）甲酸乙酯（11）和少量的1,3-二甲基-6-苯基吡嗪[2,3-d]嘧啶-2,4（1H，3H）-二酮（12）。通过单晶X射线衍射分析，明确了6和11的结构。
• Regiospecific Synthesis of 6-Alkylated Lumazine Derivatives Using Silylenol Ethers
  作者：Mamoru Igarashi、Masaru Tada

  DOI：10.1055/s-1996-4241

  日期：1996.4

  The reaction of oxadiazinone with silylenol ethers gave regiospecifically 6-substituted lumazines by an hetero Diels-Alder addition followed by decarboxylation and silanol elimination.

  通过杂环 Diels-Alder 加成，然后进行脱羧和硅烷醇消除，噁二嗪酮与硅烯醇醚反应生成了特异性 6-取代的鲁马嗪类化合物。
• Immunosuppresive effects of pteridine derivatives
  申请人：Waer Jozef Albert Mark

  公开号：US20070043000A1

  公开（公告）日：2007-02-22

  Novel poly-substituted pteridinediones (lumazines), and mono- or polysubstituted 2-thiolumazines, 4-thiolumazines or 2,4-dithiolumazines, having disclosed substituents in positions 1, 3, 6 and 7 of the pteridine ring, and pharmaceutically acceptable salts thereof, are useful as biologically active ingredients in preparing pharmaceutical compositions especially for the treatment or prevention of a CNS disorder, a cell proliferative disorder, a viral infection, an immune or auto-immune disorder or a transplant rejection. Combinations of the pteridine derivatives of the invention with an immunosuppressant or immunomodulator drug, an antineoplastic drug or an antiviral agent, providing potential synergistic effects, are also disclosed.

  新型多取代噻唑并二酮（吕马嗪），以及单取代或多取代的2-硫吕马嗪、4-硫吕马嗪或2,4-二硫吕马嗪，在噻嗪环的1、3、6和7位上具有已披露的取代基，以及其药学上可接受的盐，可用作制备药物组合物的活性成分，尤其适用于治疗或预防中枢神经系统疾病、细胞增殖紊乱、病毒感染、免疫或自身免疫性疾病或移植排斥。本发明的噻唑衍生物与免疫抑制剂或免疫调节剂、抗肿瘤药物或抗病毒药物的组合，提供潜在的协同作用。