[2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl] 6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-3-carboxylate | 1103979-73-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: [2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl] 6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-3-carboxylate
• CAS: 1103979-73-2
• 化学式: C₃₁H₃₄N₂O₉
• 分子量: 578.619
• InChiKey: LDTARGJJHYXPDP-XYOKQWHBSA-N

物化性质

• 沸点：
  775.6±60.0 °C(predicted)
• 密度：
  1.221±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl] 6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-3-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以83%的产率得到(E)-2-methoxy-5-[3'-oxo-3'-(3'',4'',5''-trimethoxyphenyl)prop-1'-enyl]phenyl 6-aminomethylnicotinate bis(hydrochloride)
  参考文献：
  名称：

  Pt(II) Complexes of a Combretastatin A-4 Analogous Chalcone: Effects of Conjugation on Cytotoxicity, Tumor Specificity, and Long-Term Tumor Growth Suppression

  摘要：

  Three dichlorido(6-aminomethylnicotinate)platinum complexes 6 comprising a combretastatin A-4 analogous chalcone were tested on a panel of 21 tumor cell lines from 9 entities. Parent chalcone 1a and the directly linked conjugate 6a exhibited excellent antiproliferative activities, similar in magnitude [average log(IC50) values of -7.3 (1a) and -7.0 (6a)] and cell line specificity but slightly different in the mechanism of apoptosis induction. While 1a and 6a caused an equally fast rise in caspase-9 in the tested cancer cell lines, the downstream effector caspase-3 built up faster in cells treated with 1a compared to 6a, yet reached an equal end level. They also had different long-term effects on the regrowth of cancer cells treated with a single dose. In contrast, conjugates 6b,c featuring longer spacers between the Pt complex and the chalcone moieties were less antiproliferative than 6a.

  DOI：

  10.1021/jm801001d
• 作为产物：
  描述：

  6-[[(叔丁氧基羰基)氨基]甲基]烟酸 、 (E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 2,4,6-三氯苯甲酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.33h， 以68%的产率得到[2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl] 6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridine-3-carboxylate
  参考文献：
  名称：

  Pt(II) Complexes of a Combretastatin A-4 Analogous Chalcone: Effects of Conjugation on Cytotoxicity, Tumor Specificity, and Long-Term Tumor Growth Suppression

  摘要：

  Three dichlorido(6-aminomethylnicotinate)platinum complexes 6 comprising a combretastatin A-4 analogous chalcone were tested on a panel of 21 tumor cell lines from 9 entities. Parent chalcone 1a and the directly linked conjugate 6a exhibited excellent antiproliferative activities, similar in magnitude [average log(IC50) values of -7.3 (1a) and -7.0 (6a)] and cell line specificity but slightly different in the mechanism of apoptosis induction. While 1a and 6a caused an equally fast rise in caspase-9 in the tested cancer cell lines, the downstream effector caspase-3 built up faster in cells treated with 1a compared to 6a, yet reached an equal end level. They also had different long-term effects on the regrowth of cancer cells treated with a single dose. In contrast, conjugates 6b,c featuring longer spacers between the Pt complex and the chalcone moieties were less antiproliferative than 6a.

  DOI：

  10.1021/jm801001d

文献信息

• Pt(II) Complexes of a Combretastatin A-4 Analogous Chalcone: Effects of Conjugation on Cytotoxicity, Tumor Specificity, and Long-Term Tumor Growth Suppression
  作者：Rainer Schobert、Bernhard Biersack、Andrea Dietrich、Sebastian Knauer、Miroslava Zoldakova、Angelika Fruehauf、Thomas Mueller

  DOI：10.1021/jm801001d

  日期：2009.1.22

  Three dichlorido(6-aminomethylnicotinate)platinum complexes 6 comprising a combretastatin A-4 analogous chalcone were tested on a panel of 21 tumor cell lines from 9 entities. Parent chalcone 1a and the directly linked conjugate 6a exhibited excellent antiproliferative activities, similar in magnitude [average log(IC50) values of -7.3 (1a) and -7.0 (6a)] and cell line specificity but slightly different in the mechanism of apoptosis induction. While 1a and 6a caused an equally fast rise in caspase-9 in the tested cancer cell lines, the downstream effector caspase-3 built up faster in cells treated with 1a compared to 6a, yet reached an equal end level. They also had different long-term effects on the regrowth of cancer cells treated with a single dose. In contrast, conjugates 6b,c featuring longer spacers between the Pt complex and the chalcone moieties were less antiproliferative than 6a.