2-α-L-arabinopyranosyl-9-hydroxy-5,11-dimethyl-6H-pyrido<4,3-b>carbazolium bromide | 103461-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-α-L-arabinopyranosyl-9-hydroxy-5,11-dimethyl-6H-pyrido<4,3-b>carbazolium bromide
• 英文别名: 2-(α-L-arabinopyranosyl)-9-hydroxyellipticinium bromide；2-α-L-arabinopyranosyl-9-hydroxyellipticinium bromide；ellipravin；2-α-L-arabinopyranosyl-9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazolium bromide；(2R,3R,4S,5S)-2-(9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-2-ium-2-yl)oxane-3,4,5-triol;bromide
• CAS: 103461-20-7
• 化学式: Br*C₂₂H₂₃N₂O₅
• 分子量: 475.339
• InChiKey: OKNKQPUDKRCBIK-MAVIPZKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-α-L-arabinopyranosyl-9-hydroxy-5,11-dimethyl-6H-pyrido<4,3-b>carbazolium bromide 在 二乙基异丙基胺 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 生成
  参考文献：
  名称：

  Structure-activity relationship study on N-glycosyl moieties through model building of DNA and ellipticine N-glycoside complex

  摘要：

  Ellipticine N-glycoside derivatives have been synthesized to elucidate the role of the N-glycosyl moiety. Model-building study of the DNA-ellipticine N-glycoside complex suggested a major groove binding of the sugar moiety and roles of the hydroxyl groups at C-2', -3', and -4'. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00219-3
• 作为产物：
  描述：

  9-acetyloxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole 在 无水碳酸镉 、 氨 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 0.17h， 生成 2-α-L-arabinopyranosyl-9-hydroxy-5,11-dimethyl-6H-pyrido<4,3-b>carbazolium bromide
  参考文献：
  名称：

  立体选择性合成9-羟基玫瑰树碱苷，新型和高活性抗肿瘤药。

  摘要：

  一系列新型且高效的抗肿瘤药物，即9-羟基石蒜碱糖苷，通过改进的缩合反应在良好产率下立体选择性地合成。该反应以碳酸镉为催化剂，将9-乙酸氧基石蒜碱与全酧化的糖基卤化物进行反应，随后用甲醇氨去除醧基。

  DOI：

  10.1248/cpb.35.3975

文献信息

• Carbohydrate Derivatives of the Antitumour Alkaloid 9-Hydroxyellipticine
  作者：Annaleise R. Grummitt、Margaret M. Harding、Pia I. Anderberg、Alison Rodger

  DOI：10.1002/1099-0690(200301)2003:1<63::aid-ejoc63>3.0.co;2-v

  日期：2003.1

  the corresponding glycosidation reactions with the quaternised ellipticines 2 and 3 which are soluble only in polar solvents. Formation of the 9-(α-L-arabinopyranosyl)ellipticine derivatives 13 and 14 was achieved by using 2,3,4-tri-O-acetyl-L-arabinopyranosyl bromide in the presence of sodium methoxide in methanol. Improved yields were obtained under the same conditions by incorporation of an ether linker

  报道了 2-萘酚的 L-阿拉伯糖基衍生物和季铵化玫瑰花碱 Celiptium (2) 和 Ellipravin (3) 的合成。Naphth-2-yl 2',3',4'-tri-O-acetyl-α-L-arabinopyranoside 在 Konigs-Knorr 和 Mitsunobu 条件下在非极性非质子溶剂中制备，并使用 2,3,4-tri-O-乙酰-L-阿拉伯吡喃基氟作为糖基供体。这些条件不适用于与仅溶于极性溶剂的季铵化玫瑰树碱 2 和 3 的相应糖苷化反应。9-(α-L-阿拉伯吡喃糖基)玫瑰树碱衍生物 13 和 14 的形成是通过在甲醇钠存在下使用 2,3,4-三-O-乙酰基-L-阿拉伯吡喃基溴在甲醇中实现的。在相同条件下通过在糖和玫瑰树碱之间掺入醚接头获得了更高的产率，得到衍生物 15 和 16。乙醇酸酯 17 和 18 是使用 2-(2',3',4'-tri -O-乙酰基
• Synthesis and antitumor activity of quaternary ellipticine glycosides, a series of novel and highly active antitumor agents
  作者：Tadashi Honda、Mika Kato、Minako Inoue、Tetsuo Shimamoto、Keiyuu Shima、Toshihiro Nakanishi、Takako Yoshida、Teruhisa Noguchi

  DOI：10.1021/jm00402a007

  日期：1988.7

  A series of ellipticine glycosides [2-N-glycosyl quaternary pyridinium salts of three ellipticines: ellipticine (1), 9-methoxyellipticine (2), and 9-hydroxyellipticine (4)] were stereoselectively synthesized in good yields by an improved condensation reaction between ellipticines [1, 2, and 9-acetoxyellipticine (3)] and protected (peracylated and perbenzylated) glycosyl halides with cadmium carbonate, followed by deprotection. These glycosides were preliminarily evaluated for their antitumor activity in the L1210 leukemia system. Twenty-six (53%) of the 49 glycosides tested were curative, and five [9-hydroxyellipticine L-arabinopyranoside (41b), D-lyxofuranoside (43a), L-lyxopyranoside (44b), D-xylofuranoside (49a), and L-rhamnopyranoside (56)] were selected for extended evaluation on the basis of their high levels of activity. The structure-activity relationships are discussed. The selected glycosides showed remarkable activity in six different murine tumor systems with excellent therapeutic ratios; their efficacy surpassed that of doxorubicin against three of these systems. On the basis of these results and ease of formulation, the two glycosides 41b (SUN4599) and 49a (SUN5073) were selected for further preclinical evaluation and possible clinical development.
• HONDA, TADASHI;INOUE, MINAKO;KATO, MIKA;SHIMA, KEIYUU;SHIMAMOTO, TETSUO, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3975-3978
  作者：HONDA, TADASHI、INOUE, MINAKO、KATO, MIKA、SHIMA, KEIYUU、SHIMAMOTO, TETSUO

  DOI：——

  日期：——
• Stereoselective synthesis of 9-hydroxyellipticine glycosides, novel and highly active antitumor agents.
  作者：Tadashi Honda、Minako Inoue、Mika Kato、Keiyuu Shima、Tetsuo Shimamoto

  DOI：10.1248/cpb.35.3975

  日期：——

  A series of novel and highly active antitumor agents, 9-hydroxyellipticine glycosides were stereoselectively synthesized in good yields by an improved condensation reaction between 9-acetoxyellipticine and peracylated glycosyl halides using cadmium carbonate, followed by the removal of acyl groups with methanolic ammonia.

  一系列新型且高效的抗肿瘤药物，即9-羟基石蒜碱糖苷，通过改进的缩合反应在良好产率下立体选择性地合成。该反应以碳酸镉为催化剂，将9-乙酸氧基石蒜碱与全酧化的糖基卤化物进行反应，随后用甲醇氨去除醧基。
• Structure-activity relationship study on N-glycosyl moieties through model building of DNA and ellipticine N-glycoside complex
  作者：Tetsuo Shimamoto、Seiichi Imajo、Tadashi Honda、Satomichi Yoshimura、Masaji Ishiguro

  DOI：10.1016/0960-894x(96)00219-3

  日期：1996.6

  Ellipticine N-glycoside derivatives have been synthesized to elucidate the role of the N-glycosyl moiety. Model-building study of the DNA-ellipticine N-glycoside complex suggested a major groove binding of the sugar moiety and roles of the hydroxyl groups at C-2', -3', and -4'. Copyright (C) 1996 Elsevier Science Ltd