2,3-di-O-benzoyl-D-erythrofuranosyl chloride | 114028-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-di-O-benzoyl-D-erythrofuranosyl chloride
• 英文别名: [(3R,4R)-4-benzoyloxy-5-chlorooxolan-3-yl] benzoate
• CAS: 114028-04-5
• 化学式: C₁₈H₁₅ClO₅
• 分子量: 346.767
• InChiKey: PCVAVDTYVZVUKG-YGFGXBMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-acetyloxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole 、 2,3-di-O-benzoyl-D-erythrofuranosyl chloride 在 无水碳酸镉 作用下， 以 硝基甲烷 为溶剂， 反应 0.17h， 生成 9-Acetoxy-2-((3R,4R)-3,4-bis-benzoyloxy-tetrahydro-furan-2-yl)-5,11-dimethyl-6H-pyrido[4,3-b]carbazol-2-ium; chloride
  参考文献：
  名称：

  Synthesis and antitumor activity of quaternary ellipticine glycosides, a series of novel and highly active antitumor agents

  摘要：

  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.

  DOI：

  10.1021/jm00402a007

文献信息

• 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。
• XONDA, TADASI;NAKANISI, TOSIXIRO
  作者：XONDA, TADASI、NAKANISI, TOSIXIRO

  DOI：——

  日期：——
• US4698423A
  申请人：——

  公开号：US4698423A

  公开（公告）日：1987-10-06
• 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.