myristinin C | 888489-66-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: myristinin C
• 英文别名: myristinin B；1-[2,4,6-trihydroxy-3-[(2R,4R)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]phenyl]dodecan-1-one
• CAS: 888489-66-5
• 化学式: C₃₃H₄₀O₇
• 分子量: 548.676
• InChiKey: JGXZVDAPLSTBGZ-VAVYLYDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 myristinin C 在 吡啶 作用下， 反应 1.5h， 以86%的产率得到penta-O-acetyl-myristinin A
  参考文献：
  名称：

  (+)-Myristinins A and D from Knema elegans, which Inhibit DNA Polymerase β and Cleave DNA

  摘要：

  A survey of crude plant extracts for DNA polymerase inhibitors resulted in the identification of a methyl ethyl ketone extract prepared from Knema elegans that strongly inhibited the enzyme. Subsequent bioassay-guided fractionation of the extract, using an assay to monitor the activity of DNA polymerase beta, led to the isolation of two potent inhibitors, (+)-myristinins A (1) and D (2), which are known flavans having unusual structures. (+)-Myristinins A and D exhibited IC50 values of 12 and 4.3 mu M, respectively, as inhibitors of DNA polymerase beta in the presence of bovine serum albumin (BSA), and 2.7 and 1:2 mu M in the absence of BSA. As such, they are the most potent DNA polymerase inhibitors reported to date. Compounds 1 and 2 potentiated the cytotoxicity of bleomycin toward cultured P388D(1) cells, reducing the number of viable cells by at least 30% when employed at 9 mu M concentration for 6 h in the presence of an otherwise nontoxic concentration of bleomycin (75 nM). Principles 1 and 2 also induced strong Cu2+-dependent DNA strand scission in a DNA cleavage assay. Accordingly, 1 and 2 exhibit two activities, namely, DNA polymerase beta inhibition and DNA damage.

  DOI：

  10.1021/np058064g
• 作为产物：
  描述：

  (2S,3R)-2-(4-benzoxyphenyl)-7-benzoxy-4-(2-hydroxyethoxy)chroman-3-yl acetate 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 myristinin C
  参考文献：
  名称：

  肉豆蔻碱B / C的阻转异构体的立体选择性合成。

  摘要：

  [反应：见正文]已经完成了一种有效的DNA破坏剂（-）-myristinin B / C的首次立体选择性合成。这种有效的合成可以明确确认阻转异构天然产物的结构和绝对立体化学。还合成了对映体（+）-肉豆蔻素B / C，为两种对映体的生物学评估提供了充足的材料。

  DOI：

  10.1021/ol060511b

文献信息

• Total synthesis of myristinins A–F and 3′-hydroxy-5,7-dimethoxy-4-<i>O</i>-2′-cycloflavan by iterative generation of <i>o</i>-quinone methides
  作者：Santosh J. Gharpure、S. Jegadeesan、Dharmendra S. Vishwakarma

  DOI：10.1039/d2nj00244b

  日期：——

  An iterative generation of o-quinone methides (o-QMs) and [4+2] cycloaddition followed by inter/intra-molecular Michael addition in a cascade sequence gave expedient access to total synthesis of myristinins A–F and 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan and their analogues, respectively. This cascade sequence cyclisation successfully provided the shortest route to the gram-scale synthesis of the

  邻醌甲基化物 ( o -QMs) 和 [4+2] 环加成，然后是级联序列中分子间/分子内 Michael 加成的迭代生成，方便了肉豆蔻素 A-F 和 3'-羟基-的全合成。分别为 5,7-dimethoxy-4- O -2'-cycloflavan 及其类似物。这种级联序列环化成功地为肉豆蔻素家族的克级合成提供了最短途径，包括首次全合成肉豆蔻素 D-F 和 3'-hydroxy-5,7-dimethoxy-4- O -2'-cycloflavan .
• Stereoselective Synthesis of the Atropisomers of Myristinin B/C
  作者：David J. Maloney、Shengxi Chen、Sidney M. Hecht

  DOI：10.1021/ol060511b

  日期：2006.4.1

  [reaction: see text] The first stereoselective synthesis of a potent DNA damaging agent, (-)-myristinin B/C, has been accomplished. This efficient synthesis allowed for unambiguous confirmation of the structure and absolute stereochemistry of the atropisomeric natural product. The antipode, (+)-myristinin B/C, was also synthesized, providing ample material for biological evaluation of both enantiomers

  [反应：见正文]已经完成了一种有效的DNA破坏剂（-）-myristinin B / C的首次立体选择性合成。这种有效的合成可以明确确认阻转异构天然产物的结构和绝对立体化学。还合成了对映体（+）-肉豆蔻素B / C，为两种对映体的生物学评估提供了充足的材料。
• (+)-Myristinins A and D from <i>Knema </i><i>e</i><i>legans</i>, which Inhibit DNA Polymerase β and Cleave DNA
  作者：Jing-Zhen Deng、Shelley R. Starck、Shisheng Li、Sidney M. Hecht

  DOI：10.1021/np058064g

  日期：2005.11.1

  A survey of crude plant extracts for DNA polymerase inhibitors resulted in the identification of a methyl ethyl ketone extract prepared from Knema elegans that strongly inhibited the enzyme. Subsequent bioassay-guided fractionation of the extract, using an assay to monitor the activity of DNA polymerase beta, led to the isolation of two potent inhibitors, (+)-myristinins A (1) and D (2), which are known flavans having unusual structures. (+)-Myristinins A and D exhibited IC50 values of 12 and 4.3 mu M, respectively, as inhibitors of DNA polymerase beta in the presence of bovine serum albumin (BSA), and 2.7 and 1:2 mu M in the absence of BSA. As such, they are the most potent DNA polymerase inhibitors reported to date. Compounds 1 and 2 potentiated the cytotoxicity of bleomycin toward cultured P388D(1) cells, reducing the number of viable cells by at least 30% when employed at 9 mu M concentration for 6 h in the presence of an otherwise nontoxic concentration of bleomycin (75 nM). Principles 1 and 2 also induced strong Cu2+-dependent DNA strand scission in a DNA cleavage assay. Accordingly, 1 and 2 exhibit two activities, namely, DNA polymerase beta inhibition and DNA damage.