Catharanthine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 依波格型生物碱
• 英文名称: Catharanthine
• 英文别名: methyl (1R,15S,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: CMKFQVZJOWHHDV-DYHNYNMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Catharanthine 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、30.0 kPa 条件下， 反应 2.0h， 以72%的产率得到isocatharanthine
  参考文献：
  名称：

  WO2008/34882

  摘要：

  公开号：

文献信息

• Total synthesis of a key series of vinblastines modified at C4 that define the importance and surprising trends in activity
  作者：Shouliang Yang、Kuppusamy Sankar、Colin K. Skepper、Timothy J. Barker、John C. Lukesh III、Daniel M. Brody、Manuela M. Brütsch、Dale L. Boger

  DOI：10.1039/c6sc04146a

  日期：——

  electron-deficient 1,3,4-oxadiazoles. Such cycloaddition cascades were used to directly introduce altered C4 substituents, providing the basis for concise total syntheses of a series of C4 modified vindolines and their subsequent single-step incorporation into the corresponding synthetic vinblastines in routes as short as 8–12 steps. Evaluation of the synthetic vinblastines revealed a surprisingly large

  详细介绍了关键的系统化长春碱系列的总合成和评估，该系列结合了C4处取代基的首次深度变化。该合成方法具有1,3,4-恶二唑[4 + 2] / [3 + 2]环加成级联反应的扩大和重新定义的范围，在该级联反应中，发现电子失配的缺电子三取代烯烃和未活化的三取代烯烃可以有效地引发该反应。环加成级联与束缚的电子缺陷型1,3,4-恶二唑。这种环加成级联反应用于直接引入改变的C4取代基，为简明的全合成一系列C4修饰的长春花碱及其随后的单步掺入相应合成长春碱的途径（短至8-12个步骤）提供了基础。合成长春花碱的评估表明，尽管以前不认为C4取代基与生物靶微管蛋白有紧密的相互作用，但其对活性的影响和作用却出乎意料。仅引入C4甲酯，即长春碱的结构异构体，其中转位C4乙酸酯的羰基碳和酯氧，即可提供与天然产物效力相匹配的合成长春碱。相反，即使引入C4乙酰胺或 提供了与天然产品功效相称的合成长春花碱。相反，即使引入C4乙酰胺或
• Synthesis and Biological Evaluation of Vinca Alkaloids and Phomopsin Hybrids
  作者：Quoc Anh Ngo、Fanny Roussi、Anthony Cormier、Sylviane Thoret、Marcel Knossow、Daniel Guénard、Françoise Guéritte

  DOI：10.1021/jm801064y

  日期：2009.1.8

  Ten hybrids of vinca alkaloids and phomopsin A have been synthesized by linking the octahydrophomopsin lateral chain to the tertiary amine of the cleavamine moiety of anhydrovinblastine (AVLB) and vinorelbine. These compounds have been elaborated in order to obtain original products that may interfere with both binding sites of vinblastine (VLB) and phomopsin in tubulin. Although NMR and molecular modeling studies have shown that the orientation of the added peptide chains of these hybrids is not the same as those of phomopsin A, most of them are very potent inhibitors of microtubules assembly and they present good cytotoxicity against KB cell line. These interesting biological activities may eventually be explained by the fact that their lateral chain resides in a pocket distinct from that of the phomopsin A peptide, at the interface of tubulins beta and alpha.