| 1233367-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1233367-89-9
• 化学式: C₂₃H₂₄N₂O₄S
• 分子量: 424.521
• InChiKey: YYJLNSAMMKKHIN-ZSLQJQOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.24
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 Et₃OBF₄ 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Total Synthesis and Evaluation of a Key Series of C5-Substituted Vinblastine Derivatives

  摘要：

  A remarkably concise seven- to eight-step total synthesis of a systematic series of key vinblastine derivatives is detailed and used to characterize the importance and probe the role of the C5 ethyl substituent (R = H, Me, Pr, CH=CH(2), C CH, CH(2)OH, and CHO vs Et). The analogues, which bear deep-seated structural changes accessible only by total synthesis, were prepared using a powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles ideally suited for use in the assemblage of the vindoline-derived lower subunit followed by their incorporation into the vinblastine analogues through the use of a single-step biomimetic coupling with catharanthine. The evaluation of the series revealed that the tubulin binding site surrounding this C5 substituent is exquisitely sensitive to the presence (Et > H, 10-fold), size (Me <= Et > Pr, 10-fold), shape (Et > CH=CH(2) and C CH, >4-fold), and polarity (Et > CHO > CH(2)OH, >10-20-fold) of this substituent and that on selected occasions only a C5 methyl group may provide analogues that approach the activity observed with the naturally occurring C5 ethyl group.

  DOI：

  10.1021/ja1027748
• 作为产物：
  描述：

  在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以67%的产率得到
  参考文献：
  名称：

  Total Synthesis and Evaluation of a Key Series of C5-Substituted Vinblastine Derivatives

  摘要：

  A remarkably concise seven- to eight-step total synthesis of a systematic series of key vinblastine derivatives is detailed and used to characterize the importance and probe the role of the C5 ethyl substituent (R = H, Me, Pr, CH=CH(2), C CH, CH(2)OH, and CHO vs Et). The analogues, which bear deep-seated structural changes accessible only by total synthesis, were prepared using a powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of 1,3,4-oxadiazoles ideally suited for use in the assemblage of the vindoline-derived lower subunit followed by their incorporation into the vinblastine analogues through the use of a single-step biomimetic coupling with catharanthine. The evaluation of the series revealed that the tubulin binding site surrounding this C5 substituent is exquisitely sensitive to the presence (Et > H, 10-fold), size (Me <= Et > Pr, 10-fold), shape (Et > CH=CH(2) and C CH, >4-fold), and polarity (Et > CHO > CH(2)OH, >10-20-fold) of this substituent and that on selected occasions only a C5 methyl group may provide analogues that approach the activity observed with the naturally occurring C5 ethyl group.

  DOI：

  10.1021/ja1027748