6-oxovincamine | 65825-93-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: 6-oxovincamine
• 英文别名: 6-keto-vincamine；6-ketovincamine；methyl (15S,17S,19S)-15-ethyl-17-hydroxy-9-oxo-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate
• CAS: 65825-93-6
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: CSZMJHLPPJDDBA-GIVPXCGWSA-N

物化性质

• 沸点：
  530.7±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-oxovincamine 在 palladium on activated charcoal 盐酸 、 mercury(II) diacetate 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 6-hydroxy-py-tetrahydro-16-deoxyepivincamine chloride
  参考文献：
  名称：

  Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids

  摘要：

  Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)(2) or TI(OCOCF3)(3) in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.

  DOI：

  10.3987/com-93-6481
• 作为产物：
  描述：

  长春胺 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以24%的产率得到6-oxovincamine
  参考文献：
  名称：

  Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids

  摘要：

  Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)(2) or TI(OCOCF3)(3) in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.

  DOI：

  10.3987/com-93-6481

文献信息

• Cerebral vasodilating 6-substituted vincamines
  申请人：Enrico Corvi Mora

  公开号：US04140777A1

  公开（公告）日：1979-02-20

  The invention relates to novel derivatives of vincamine and apovincamine having the formula ##STR1## WHICH ARE ENDOWED WITH ANALOGOUS PROPERTIES AS THE VINCAMINE AND APOVINCAMINE AS WELL AS WITH AN EXTENDED EFFECT. The invention relates also to the methods for the preparation of the above derivatives.

  该发明涉及具有以下公式的新型维因卡明和阿波维因卡明衍生物，其具有类似于维因卡明和阿波维因卡明的性质以及具有延长效果。该发明还涉及上述衍生物的制备方法。
• Vereczkey; Tamas; Czira, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 11, p. 1861 - 1865
  作者：Vereczkey、Tamas、Czira、Szporny

  DOI：——

  日期：——
• Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids
  作者：Guy Lewin、Corinne Schaeffer、Alain Pierr�、Nicolas Guilbaud、Ghanem Atassi、Jacques Poisson

  DOI：10.3987/com-93-6481

  日期：——

  Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)(2) or TI(OCOCF3)(3) in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.