D-ribose 5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazone

• 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: D-ribose 5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazone
• 英文别名: (2R,3S,4S,5E)-5-[(5-ethyl-[1,2,4]triazino[5,6-b]indol-3-yl)hydrazinylidene]pentane-1,2,3,4-tetrol
• 化学式: C₁₆H₂₀N₆O₄
• 分子量: 360.373
• InChiKey: XECIWLFOSCJAFC-LTPJSPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  149
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  D-ribose 5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazone 在 吡啶 、 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 生成 10-ethyl-3-(D-ribo-1,2,3,4-tetraacetoxybut-1-yl)-1,2,4-triazolo[4',3':2,3]-[1,2,4]triazino[5,6-b]indole
  参考文献：
  名称：

  Sterically Controlled Regiospecific Cyclization of Aldose-5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazones to Linearly Annelated 3-Polyhydroxyalkyl-10-ethyl-1,2,4-triazolo-[4′,3′:2,3]-1,2,4-triazino[5,6-b]indoles

  摘要：

  Condensation of aldoses with 5-ethyl-3-hydrazino-1,2,4-triazino[5,6-b]indole gave the corresponding aldose-5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazones which were acetylated to their poly-O-acetyl derivatives. The latter underwent sterically controlled regiospecific oxidative cyclization with bromine in acetic acid and sodium acetate to sterically favourable linearly annelated 3-polyacetoxyalkyl-10-ethyl-1,2,4-triazole[4',3':2,3]-1,2,4-triazino[5,6-b]indoles rather than to their sterically unfavourable angularly annelated regioisomers. The regiospecific outcome of this heterocyclization is discussed in terms of electronic as well as steric factors, and the assigned structures have been corroborated on the basis of chemical as well as spectroscopic evidence. De-O-acetylation of the acetoxyindoles with ammonium hydroxide in methanol gave the title compounds. Representative members of the prepared compounds were tested for antimicrobial activity.

  DOI：

  10.1007/pl00010316
• 作为产物：
  描述：

  D-核糖 、 5-ethyl-3-hydrazino-5H-1,2,4-triazino<5,6-b>indole 以 乙醇 、 水 为溶剂， 反应 0.25h， 以70%的产率得到D-ribose 5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazone
  参考文献：
  名称：

  Sterically Controlled Regiospecific Cyclization of Aldose-5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazones to Linearly Annelated 3-Polyhydroxyalkyl-10-ethyl-1,2,4-triazolo-[4′,3′:2,3]-1,2,4-triazino[5,6-b]indoles

  摘要：

  Condensation of aldoses with 5-ethyl-3-hydrazino-1,2,4-triazino[5,6-b]indole gave the corresponding aldose-5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazones which were acetylated to their poly-O-acetyl derivatives. The latter underwent sterically controlled regiospecific oxidative cyclization with bromine in acetic acid and sodium acetate to sterically favourable linearly annelated 3-polyacetoxyalkyl-10-ethyl-1,2,4-triazole[4',3':2,3]-1,2,4-triazino[5,6-b]indoles rather than to their sterically unfavourable angularly annelated regioisomers. The regiospecific outcome of this heterocyclization is discussed in terms of electronic as well as steric factors, and the assigned structures have been corroborated on the basis of chemical as well as spectroscopic evidence. De-O-acetylation of the acetoxyindoles with ammonium hydroxide in methanol gave the title compounds. Representative members of the prepared compounds were tested for antimicrobial activity.

  DOI：

  10.1007/pl00010316

文献信息

• Sterically Controlled Regiospecific Cyclization of Aldose-5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazones to Linearly Annelated 3-Polyhydroxyalkyl-10-ethyl-1,2,4-triazolo-[4′,3′:2,3]-1,2,4-triazino[5,6-b]indoles
  作者：Mohammed A. E. Shaban、Mamdouh A. M. Taha、Ali E. A. Morgaan

  DOI：10.1007/pl00010316

  日期：2000.5.17

  Condensation of aldoses with 5-ethyl-3-hydrazino-1,2,4-triazino[5,6-b]indole gave the corresponding aldose-5-ethyl-1,2,4-triazino[5,6-b]indol-3-ylhydrazones which were acetylated to their poly-O-acetyl derivatives. The latter underwent sterically controlled regiospecific oxidative cyclization with bromine in acetic acid and sodium acetate to sterically favourable linearly annelated 3-polyacetoxyalkyl-10-ethyl-1,2,4-triazole[4',3':2,3]-1,2,4-triazino[5,6-b]indoles rather than to their sterically unfavourable angularly annelated regioisomers. The regiospecific outcome of this heterocyclization is discussed in terms of electronic as well as steric factors, and the assigned structures have been corroborated on the basis of chemical as well as spectroscopic evidence. De-O-acetylation of the acetoxyindoles with ammonium hydroxide in methanol gave the title compounds. Representative members of the prepared compounds were tested for antimicrobial activity.