1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-pent-2-enyl)-undec-6-enyloxymethyl]-4-methoxy-benzene | 870075-26-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-pent-2-enyl)-undec-6-enyloxymethyl]-4-methoxy-benzene
• CAS: 870075-26-6
• 化学式: C₄₄H₈₂O₆Si₂
• 分子量: 763.302
• InChiKey: HRSCDNQBWWBPPW-NFPXFGQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.46
• 重原子数：
  52.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-pent-2-enyl)-undec-6-enyloxymethyl]-4-methoxy-benzene 在 咪唑 、 盐酸 、 甲基锂 、 碘 、 N,N-二异丙基乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 (5R,6S)-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-6-methoxymethoxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16-trienyl]-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Simplified Analogues of (+)-Discodermolide. Additional Insights on the Importance of the Diene, the C(7) Hydroxyl, and the Lactone

  摘要：

  The design, synthesis, and biological evaluation of seven totally synthetic analogues of the antitumor agent (+)-discodermolide are reported. lid Saturation of the terminal diene system, alteration of the substituents on the lactone, and alkylation of the C(7)-hydroxyl group reveal significant structure-activity relationships.

  DOI：

  10.1021/ol052070m
• 作为产物：
  描述：

  (Z)-(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2,4,6-trimethyl-dec-7-en-1-ol 在 碘 、 三苯基膦 作用下， 生成 1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((Z)-(S)-1-methyl-pent-2-enyl)-undec-6-enyloxymethyl]-4-methoxy-benzene
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Simplified Analogues of (+)-Discodermolide. Additional Insights on the Importance of the Diene, the C(7) Hydroxyl, and the Lactone

  摘要：

  The design, synthesis, and biological evaluation of seven totally synthetic analogues of the antitumor agent (+)-discodermolide are reported. lid Saturation of the terminal diene system, alteration of the substituents on the lactone, and alkylation of the C(7)-hydroxyl group reveal significant structure-activity relationships.

  DOI：

  10.1021/ol052070m

文献信息

• [EN] DISCODERMOLIDE ANALOGUES AND METHODS OF THEIR USE<br/>[FR] ANALOGUES DE DISCODERMOLIDE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV PENNSYLVANIA

  公开号：WO2009006184A1

  公开（公告）日：2009-01-08

  6- and 7-substituted coumarin and related 6- and 7-substituted lH-quinolin-2-one compounds, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the 7-substituted coumarin and related 7-substituted lH-quinolin-2-one compounds mimic or exceed the high level of pharmacological activity of discodermolide. In other embodiments, their preparation involves more readily available materials, higher yield processes and/or simpler synthetic sequences. In yet other embodiments, the compounds of the invention represent structurally simpler, therapeutically active analogues of discodermolide than heretofore known and may be useful as microtubule stabilizers and, inter alia, for treating and/or preventing cancer and other diseases, disorders, and/or conditions mediated by the stabilization of microtubules.

  揭示了6-和7-取代香豆素及相关的6-和7-取代的lH-喹啉-2-酮化合物，含有这些化合物的药物组合物，以及其药用方法。在某些实施例中，7-取代香豆素和相关的7-取代lH-喹啉-2-酮化合物模拟或超过了discodermolide的高水平药理活性。在其他实施例中，它们的制备涉及更容易获得的材料、更高产率的过程和/或更简单的合成序列。在另一些实施例中，本发明的化合物代表比以往已知的discodermolide结构上更简单、在治疗上活性更强的类似物，可能有用作微管稳定剂，用于治疗和/或预防由微管稳定引起的癌症和其他疾病、紊乱和/或状况。