3-Bromopropyl Picropodophyllate | 1207260-85-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 3-Bromopropyl Picropodophyllate
• 英文别名: 3-bromopropyl (5R,6S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
• CAS: 1207260-85-2
• 化学式: C₂₅H₂₉BrO₉
• 分子量: 553.404
• InChiKey: VFQOUWMGTZTUKY-PARPOCPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-Bromopropyl Picropodophyllate 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 78.5h， 生成 3-(6-chloropurin-9-yl)propyl (5R,6S,7R,8R)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
  参考文献：
  名称：

  Lignopurines: A new family of hybrids between cyclolignans and purines. Synthesis and biological evaluation

  摘要：

  A new family of hybrids between cyclolignans related to podophyllic aldehyde, a non-lactonic cyclolignan, and purines were prepared and evaluated against several human tumour cell lines. Both fragments, cyclolignan and purine, were linked through aliphatic and aromatic chains. The influence on the cytotoxicity of the purine substitution and the nature of the linker is analyzed. The new family was slightly less cytotoxic than the parent podophyllic aldehyde, although the selectivity is maintained or even improved and among the linkers used, the presence of an aromatic ring gave the most potent and selective derivatives within the new series tested. Cell cycle and confocal studies demonstrate that these derivatives interfere with the tubulin polymerization and arrest cells at the G(2)/M phase, in the same way than the parent compounds podophyllotoxin and podophyllic aldehyde do. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.026
• 作为产物：
  描述：

  1,3-二溴丙烷 、 picropodophyllic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以82%的产率得到3-Bromopropyl Picropodophyllate
  参考文献：
  名称：

  具有细胞毒和细胞凋亡诱导作用的新型鬼臼醛衍生物的合成及生物学评价

  摘要：

  制备了几种非内分泌的鬼臼醛类似物，并针对几种人类肿瘤细胞系进行了评估。他们在cyclolignan骨架的C-9和C-9'处具有醛，亚胺，胺，酯和酰胺官能团的不同组合。合成的所有化合物均显示在μM或以下的细胞毒性水平。在测试的新系列中，在C-9处具有醛或亚胺，在C-9'具有酯的化合物是最有效的，其GI 50值在nM范围内，其中一些对HT-29的效力高出几倍。与A-549癌相比，它可抗MB-231黑色素瘤细胞。细胞周期研究和对微管破坏能力的分析表明，对于结构密切相关的化合物，存在两种不同的细胞死亡诱导机制。

  DOI：

  10.1021/jm901373w

文献信息

• Synthesis and Biological Evaluation of New Podophyllic Aldehyde Derivatives with Cytotoxic and Apoptosis-Inducing Activities
  作者：M Ángeles Castro、José M Miguel del Corral、Pablo A. García、M Victoria Rojo、Janis de la Iglesia-Vicente、Faustino Mollinedo、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1021/jm901373w

  日期：2010.2.11

  Several series of nonlactonic podophyllic aldehyde analogues were prepared and evaluated against several human tumor cell lines. They had different combinations of aldehyde, imine, amine, ester, and amide functions at C-9 and C-9′ of the cyclolignan skeleton. All the compounds synthesized showed cytotoxicity levels in the μM range and below. Within the new series tested, compounds having an aldehyde

  制备了几种非内分泌的鬼臼醛类似物，并针对几种人类肿瘤细胞系进行了评估。他们在cyclolignan骨架的C-9和C-9'处具有醛，亚胺，胺，酯和酰胺官能团的不同组合。合成的所有化合物均显示在μM或以下的细胞毒性水平。在测试的新系列中，在C-9处具有醛或亚胺，在C-9'具有酯的化合物是最有效的，其GI 50值在nM范围内，其中一些对HT-29的效力高出几倍。与A-549癌相比，它可抗MB-231黑色素瘤细胞。细胞周期研究和对微管破坏能力的分析表明，对于结构密切相关的化合物，存在两种不同的细胞死亡诱导机制。
• Lignopurines: A new family of hybrids between cyclolignans and purines. Synthesis and biological evaluation
  作者：Ma Ángeles Castro、José Ma. Miguel del Corral、Pablo A. García、Ma Victoria Rojo、Ana C. Bento、Faustino Mollinedo、Andrés M. Francesch、Arturo San Feliciano

  DOI：10.1016/j.ejmech.2012.10.026

  日期：2012.12

  A new family of hybrids between cyclolignans related to podophyllic aldehyde, a non-lactonic cyclolignan, and purines were prepared and evaluated against several human tumour cell lines. Both fragments, cyclolignan and purine, were linked through aliphatic and aromatic chains. The influence on the cytotoxicity of the purine substitution and the nature of the linker is analyzed. The new family was slightly less cytotoxic than the parent podophyllic aldehyde, although the selectivity is maintained or even improved and among the linkers used, the presence of an aromatic ring gave the most potent and selective derivatives within the new series tested. Cell cycle and confocal studies demonstrate that these derivatives interfere with the tubulin polymerization and arrest cells at the G(2)/M phase, in the same way than the parent compounds podophyllotoxin and podophyllic aldehyde do. (C) 2012 Elsevier Masson SAS. All rights reserved.