methyl 7α-hydroxy-8β,14β-dioxopodocarpan-13β-oate | 623924-12-9

• 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: methyl 7α-hydroxy-8β,14β-dioxopodocarpan-13β-oate
• 英文别名: methyl (1R,2R,4aR,4bS,8aS,10R,10aS)-1,10a-diformyl-10-hydroxy-4b,8,8-trimethyl-2,3,4,4a,5,6,7,8a,9,10-decahydro-1H-phenanthrene-2-carboxylate
• CAS: 623924-12-9
• 化学式: C₂₁H₃₂O₅
• 分子量: 364.482
• InChiKey: LUEUZEKWPWPADA-WTEOKLBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 7α-hydroxy-8β,14β-dioxopodocarpan-13β-oate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以99%的产率得到methyl 15,17-epoxy-7α,17-dihydroxy-ent-isocopalan-16-oate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel C7-Functionalized spongiane diterpenes

  摘要：

  Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hvdroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity, while the presence of a butyrate ester led to more active compounds (CC50 = 4.0-9.5 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00230-x
• 作为产物：
  描述：

  <3R-(3aα,5aS,7aα,11aβ,11bα)>-(+)-methyl 1,3,3a,6,7,7a,8,9,10,11,11a,11b-dodecahydro-6α-hydroxy-8,8,11a-trimethyl-2H-cyclobuta-phenanthrene-3β-carboxylate 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 methyl 7α-hydroxy-8β,14β-dioxopodocarpan-13β-oate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of novel C7-Functionalized spongiane diterpenes

  摘要：

  Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hvdroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity, while the presence of a butyrate ester led to more active compounds (CC50 = 4.0-9.5 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00230-x

文献信息

• Synthesis and cytotoxic activity of novel C7-Functionalized spongiane diterpenes
  作者：Manuel Arnó、Liliana Betancur-Galvis、Miguel A. González、Jelver Sierra、Ramón J. Zaragozá

  DOI：10.1016/s0968-0896(03)00230-x

  日期：2003.7

  Based on two lead cytotoxic spongiane diterpenes, a new series of C7-oxygenated derivatives were synthesized and evaluated for their antitumor activity in vitro against the cancer cell lines HeLa and HEp-2. In general, introduction of either hvdroxyl or acetoxy groups at C-7 did not improve the resultant cytotoxicity, while the presence of a butyrate ester led to more active compounds (CC50 = 4.0-9.5 muM). (C) 2003 Elsevier Science Ltd. All rights reserved.