6-methyl-9-hydroxyellipticine | 56501-52-1

• 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: 6-methyl-9-hydroxyellipticine
• 英文别名: 9-hydroxy-6-methylellipticine；5,6,11-trimethyl-6H-pyrido[4,3-b]carbazol-9-ol；9-hydroxy-5,6,11-trimethyl-6H-pyrido[4,3-b]carbazole；9-Hydroxy-5,6,11-trimethyl-6H-pyrido<4,3-b>carbazol；9-Hydroxy-6-methylellipticin；6H-Pyrido(4,3-b)carbazol-9-ol, 5,6,11-trimethyl-；5,6,11-trimethylpyrido[4,3-b]carbazol-9-ol
• CAS: 56501-52-1
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: KVURWBFRLHGVNP-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C (decomp)
• 沸点：
  536.2±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-9-hydroxyellipticine 在 Amberlite IRA-900 (chloride form) 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-(N-Boc-5-aminopentyl)-9-hydroxy-6-methylellipticinium chloride
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032
• 作为产物：
  描述：

  3-(2,2-diethoxyethylaminomethyl)-1,4,9-trimethylcarbazole 在 吡啶 、 盐酸 、 乌洛托品 、 硫酸 、 双氧水 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 15.33h， 生成 6-methyl-9-hydroxyellipticine
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032

文献信息

• An Expedient Synthesis of 9-Hydroxyellipticine
  作者：Johannes P. M. Plug、Gerrit-Jan Koomen、Upendra K. Pandit

  DOI：10.1055/s-1992-26342

  日期：——

  9-Hydroxyellipticine (9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]-carbazole) has been synthesized from ellipticine via a direct regioselective formylation, followed by a Baeyer-Villiger oxidation.

  9-羟基胶回春碱（9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]-carbazole）通过对胶回春碱的直接区域选择性甲酰化合成，随后进行Baeyer-Villiger氧化反应。
• Regiospecific C-9 substitution of ellipticine derivatives
  作者：Albert Langendoen、Johannes P.M. Plug、Gerrit-Jan Koomen、Upendra K. Pandit

  DOI：10.1016/s0040-4020(01)80040-5

  日期：1989.1

  6-Methylellipticine (6) undergoes acylation at the C(9)-position, under Friedel Crafts reaction conditions. The C(9)-formyl compound (8) rearranges to the corresponding hydroxy derivative (9) upon treatment with hydrogen peroxide, in methanol, in the presence of sulphuric acid. The two steps provide a convenient procedure for the specific C(9)-hydroxylation of the ellipticine template.

  6-甲基玫瑰树碱（6）在Friedel Crafts反应条件下在C（9）位置进行酰化。在甲醇中，在硫酸存在下，用过氧化氢处理后，C（9）-甲酰基化合物（8）重排为相应的羟基衍生物（9）。这两个步骤为玫瑰树碱模板的特定C（9）-羟基化提供了便利的程序。
• 9-Acyloxy-5,11-dimethyl-6H-pyrido[4,3-B]carbazoles
  申请人：Hoffmann-La Roche Inc.

  公开号：US03933827A1

  公开（公告）日：1976-01-20

  9-Acyloxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazoles of the formula ##SPC1## Wherein R.sub.1 is acyl and R.sub.2 is hydrogen or lower alkyl, are described. The end products actively inhibit the growth of transplantable tumors, and are therefore useful as cytostatic agents.

  公式为##SPC1##的9-酰氧基-5,11-二甲基-6H-吡啶并[4,3-b]咔唑化合物被描述。其中R.sub.1为酰基，R.sub.2为氢或低碳基。最终产物能够有效抑制移植性肿瘤的生长，因此可用作抑制细胞生长的药剂。
• Sythesis of novel annulated ellipticines via Claisen rearrangement reactions
  作者：Johannes P.M. Plug、Gerrit-Jan Koomen、Upendra K. Pandit

  DOI：10.1016/0040-4039(92)88171-z

  日期：1992.4

  Attempted strategies for the synthesis of 10-formyl-9-hydroxyellipticine led to novel ring A and rings A/B/C annulated ellipticine derivatives.

  尝试合成10-甲酰基-9-羟基玫瑰树碱的策略导致了新的A环和A / B / C环化玫瑰树碱衍生物。
• Ellipticine derivative and production process thereof
  申请人：SUNTORY LIMITED

  公开号：EP0173462A2

  公开（公告）日：1986-03-05

  An ellipticine derivative having the general formula: wherein R represents a hydrogen atom, a hydroxyl group, an alkoxyl group having 1 to 4 carbon atoms, or an acyloxy group having 2 to 7 carbon atoms; R2 represents an aldose residue, a deoxyaldose residue, an N-acylaminoaldose residue having a substituted acyl group with 2 to 4 carbon atoms bonded to the N atom, an aldohexuronic amide residue, and aldohexuronic acid residue, an acylated aldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated deoxyaldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated N-acylaminoaldose residue having an amino group substituted with an acyl group with 2 to 4carbon atoms and having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic amide residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic acid residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an acylated aldohexuronic acid ester residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 2 to 4 carbon atoms or an arylacyl group with 7 to 9 carbon atoms, an arylalkylated aldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated deoxyaldose residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an alkylacyl group with 7 to 8 carbon atoms, an arylalkylated N-acylaminoaldose residue having an amino group with an acyl group with 2 to 4 carbon atoms and having, substituted for the hydrogen of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic amide residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic acid residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms, an arylalkylated aldohexuronic acid ester residue having, substituted for the hydrogen atom of the hydroxyl group of the sugar, an arylalkyl group with 7 to 8 carbon atoms; and R3 represents a hydrogen atom, a linear, branched, cyclic, or cyclic-linear alkyl group having 1 to 5 carbon atoms; X0 represents a pharmaceutically acceptable inorganic or organic acid anion; and the bond represented by N⊕ - R2 in the general formula (I) represents a glycoside bond between a nitrogen atom in the 2-position of the ellipticine and a carbon atom in the 1-position of the sugar. These ellipticine derivatives have a strong antineoplastic or antitumor activity and, therefore, are expected to be effective as an antineoplastic or antitumor agent.

  一种具有通式的鞣花碱衍生物： 其中 R 代表氢原子、羟基、具有 1 至 4 个碳原子的烷氧基或具有 2 至 7 个碳原子的酰氧基； R2 代表醛糖残基、脱氧醛糖残基、N-酰氨基醛糖残基（其 N 原子上键有 2 至 4 个碳原子的取代酰基）、醛缩脲酰胺残基、醛缩脲酸残基、酰化醛糖残基（其糖羟基的氢原子被取代）、一种酰化脱醛糖残基，其糖羟基的氢原子被 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代、酰化的 N-酰氨基醛糖残基，其氨基被 2 至 4 个碳原子的酰基取代，并具有 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代糖羟基的氢原子；酰化的醛缩酰胺残基，其具有一种酰化的醛缩己脲酰胺残基，其糖的羟基的氢原子被 2 至 4 个碳原子的烷酰基或 7 至 9 个碳原子的芳酰基取代、酰化醛缩醛酸酯残基，其糖羟基的氢原子被 2 至 4 个碳原子的烷基酰基或 7 至 9 个碳原子的芳基酰基取代、芳烷基化脱醛糖残基，其糖的羟基的氢原子被 7 至 8 个碳原子的烷酰基取代；芳烷基化 N-酰氨基醛糖残基，其氨基带有 2 至 4 个碳原子的酰基，并具有一种芳烷基化的醛缩脲酰胺残基，其氨基具有 2 至 4 个碳原子的酰基，并具有 7 至 8 个碳原子的芳烷基取代糖的羟基的氢原子、一种芳烷基化的醛缩脲酸酯残基，其糖的羟基的氢原子被具有 7 至 8 个碳原子的芳烷基取代；和 R3 代表氢原子、具有 1 至 5 个碳原子的直链、支链、环状或环状直链烷基； X0 代表药学上可接受的无机或有机酸阴离子；以及 通式（I）中 N⊕ - R2 所代表的键代表鞣花碱 2 位上的氮原子与糖 1 位上的碳原子之间的糖苷键。这些鞣花碱衍生物具有很强的抗肿瘤或抗肿瘤活性，因此有望成为有效的抗肿瘤或抗肿瘤药物。