ethyl (5,6-diamino-4-hydroxypyridin-2-yl)carbamate | 86970-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl (5,6-diamino-4-hydroxypyridin-2-yl)carbamate
• 英文别名: Ethyl (5,6-diamino-4-oxo-1,4-dihydropyridin-2-yl)carbamate；ethyl N-(5,6-diamino-4-oxo-1H-pyridin-2-yl)carbamate
• CAS: 86970-42-5
• 化学式: C₈H₁₂N₄O₃
• 分子量: 212.208
• InChiKey: VTSNAMTVIFIWFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (6-Amino-4-hydroxy-5-nitro-pyridin-2-yl)-carbamic acid ethyl ester 在 镍 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 ethyl (5,6-diamino-4-hydroxypyridin-2-yl)carbamate
  参考文献：
  名称：

  合成潜在的抗癌药。吡啶并[4,3-b] [1,4]恶嗪和吡啶并[4,3-b] [1,4]噻嗪。

  摘要：

  （6-氨基-4-氯-5-硝基吡啶-2-基氨基甲酸乙酯）（3）的甲酸与甲酸的水解，得到相应的4-羟基吡啶4。4的硝基的催化氢化得到5 -氨基-4-羟基吡啶5，在室温下与α-卤代酮在乙酸中反应，得到一系列3-和2,3-取代的乙基（5-氨基-2H-吡啶[4,3-b ] [1,4]恶嗪-7-基）氨基甲酸酯8.用热的浓盐酸处理8，再生吡啶合成子5.在3与硫代乙酸酯的反应中，产物进行水解和空气氧化，得到相应的二硫键6.同时还原6的硝基和二硫键得到5-氨基-4-巯基吡啶7将其与α-卤代酮在室温下于乙酸中或在乙醇和水的混合物中在回流下反应，得到一系列3-，2,3-和2,2,3-取代的乙基（5-氨基-2H-吡啶并[4,3-b] [1,4]噻嗪-7-基）氨基甲酸酯9.这些吡啶并恶嗪和吡啶并噻嗪对培养的L1210细胞增殖和有丝分裂指数以及小鼠存活的影响确定患有P388白血病。

  DOI：

  10.1021/jm00365a012

文献信息

• Pyrido(4,3-b)(1,4) oxazines and pyrido(4,3-b) (1,4)thiazines
  申请人：Southern Research Institute

  公开号：EP0107130A1

  公开（公告）日：1984-05-02

  There are disclosed certain 2H-pyrido[4,3-b]-[1,4]oxazines and 2H-pyrido[4,3-b][1,4]thiazines which posses biological activity. The compounds have the structure: wherein n has a value of 1,2 or 3; X is oxygen or sulfur; R, is a lower alkyl group, e.g., an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc.; R2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; alkenyl radicals having from about two to about 15 carbon atoms, preferably from about two to about 10 carbon atoms; cycloalkyl radicals having from about three to about 20 carbon atoms, preferably from about three to about 15 carbon atoms: aryl, aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 15 carbon atoms; a halogen radical, e.g., chlorine, fluorine, bromine and iodine; a hydroxyl group; an amino group; a nitro group; an alkoxy or aryloxy group; a carboxyl group or an alkylcarboxyl group having from about one to about 10 carbon atoms, preferably from about one to about five carbon atoms; an alkylthio group or an arylthio group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl, amino, alkoxy or aryloxy; when taken together with the aromatic ring to which it is attached, a fused ring structure such as naphthyl; and, when taken together with R., an alkylene radical containing from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; R3 is hydrogen, methyl, phenyl or, when taken with R2, an alkylene radical as previously defined; R4 is hydrogen or methyl: R3 and R4, when taken together are the radical = 0; and R5 and R6 are both hydrogen, or one is hydrogen and the other is the radical or where taken together are the radical = CHN(CH3)2-

  已公开的某些 2H-吡啶并[4,3-b]-[1,4]噁嗪和 2H-吡啶并[4,3-b][1,4]噻嗪具有生物活性。这些化合物的结构如下 其中 n 的值为 1、2 或 3；X 为氧或硫；R 为低级烷基，例如R，是低级烷基，例如，含有最多六个碳原子的烷基，如甲基、乙基、丙基、丁基等； R2 是选自下列化合物的成员R2 是选自以下组别的成员：氢、具有约 1 至约 12 个碳原子，最好是约 1 至约 6 个碳原子的烷基；具有约 2 至约 15 个碳原子，最好是约 2 至约 10 个碳原子的烯基；具有约 3 至约 20 个碳原子，最好是约 3 至约 15 个碳原子的环烷基；具有约 6 至约 20 个碳原子，最好是约 6 至约 15 个碳原子的芳基、芳烷基和烷芳基；卤素基，例如：氯、氟、溴、氨、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、醚、羟基；氨基；硝基；烷氧基或芳氧基；羧基或烷基羧基，具有约 1 至约 10 个碳原子，最好是约 1 至约 5 个碳原子；具有约 1 至约 20 个碳原子，最好是 1 至约 15 个碳原子的烷硫基或芳硫基； 具有约 1 至约 20 个碳原子，最好是 1 至约 15 个碳原子的磺酸基或烷基或芳基磺酰基；具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子的烷基或芳基亚磺酰基； 具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子的烷基或芳基单氨基或二氨基； 如上定义的烃基，带有卤素、羟基、氨基、烷氧基或芳氧基；当与所连接的芳环一起时，为融合环结构，如萘基；当与 R.,R3 是氢、甲基、苯基，或当与 R2 结合时，是如前定义的亚烷基；R4 是氢或甲基：R3 和 R4 合在一起时是基=0；R5 和 R6 都是氢，或一个是氢，另一个是基 或 R5 和 R6 同为基时 = CHN(CH3)2-
• US4451650A
  申请人：——

  公开号：US4451650A

  公开（公告）日：1984-05-29