8(R,S)-ethyl-2-(5-fluoro-2-oxo-1,2-dihydroindol-3-ylidene)-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-azacyclopentanaphthalene-1,4,7-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 8(R,S)-ethyl-2-(5-fluoro-2-oxo-1,2-dihydroindol-3-ylidene)-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-azacyclopentanaphthalene-1,4,7-trione
• 英文别名: (7E)-4-ethyl-7-(5-fluoro-2-oxo-1H-indol-3-ylidene)-4-hydroxy-1,8-dihydropyrano[3,4-f]indolizine-3,6,10-trione
• 化学式: C₂₁H₁₅FN₂O₆
• 分子量: 410.358
• InChiKey: BEOUZOQTTSXGRW-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氟靛红 、 4'-乙基-7'，8'-二氢-4'-羟基-螺[1,3-二氧戊环-2,6'（3'H）-[1H]吡喃并[3,4-f]吲哚嗪]-3′，10′（4′H）-二酮-d5 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 8(R,S)-ethyl-2-(5-fluoro-2-oxo-1,2-dihydroindol-3-ylidene)-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-azacyclopentanaphthalene-1,4,7-trione
  参考文献：
  名称：

  Rigid Analogs of Camptothecin as DNA Topoisomerase I Inhibitors

  摘要：

  Substituted 8-ethyl-2-(2-oxo-1,2-dihydroindol-3-ylidene)-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-azacyclopenta[b]naphthalene-1,4,7-triones were synthesized and evaluated as topoisomerase I inhibitors in an in vitro cleavable complex assay. The activity of these compounds may be attributed to their rigid, planar geometry, and an attempt was made to correlate the SAR in this series to known attributes of camptothecin.

  DOI：

  10.1021/jm00006a008

文献信息

• Rigid Analogs of Camptothecin as DNA Topoisomerase I Inhibitors
  作者：Karen Lackey、Jeffrey M. Besterman、Wade Fletcher、Peter Leitner、Bradley Morton、Daniel D. Sternbach

  DOI：10.1021/jm00006a008

  日期：1995.3

  Substituted 8-ethyl-2-(2-oxo-1,2-dihydroindol-3-ylidene)-8-hydroxy-2,3,5,8-tetrahydro-6-oxa-3a-azacyclopenta[b]naphthalene-1,4,7-triones were synthesized and evaluated as topoisomerase I inhibitors in an in vitro cleavable complex assay. The activity of these compounds may be attributed to their rigid, planar geometry, and an attempt was made to correlate the SAR in this series to known attributes of camptothecin.