5-chloro-3-[4-methoxy-3-(2-methoxyethoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)pyridine | 847063-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-chloro-3-[4-methoxy-3-(2-methoxyethoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)pyridine
• CAS: 847063-33-6
• 化学式: C₂₅H₂₈ClNO₇
• 分子量: 489.953
• InChiKey: JJCMACKLNRDENT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-chloro-3-[4-methoxy-3-(2-methoxyethoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)pyridine 在 Lindlar's catalyst sodium hydroxide 、 氢气 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 2-methoxy-5-[2-(3,4,5-trimethoxy-phenyl)-pyridin-3-yl]-phenol
  参考文献：
  名称：

  Heterocyclic and Phenyl Double-Bond-Locked Combretastatin Analogues Possessing Potent Apoptosis-Inducing Activity in HL60 and in MDR Cell Lines

  摘要：

  Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 < 1 muM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.

  DOI：

  10.1021/jm049622b
• 作为产物：
  描述：

  (Z)-N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate 、 2-[4-Methoxy-3-(2-methoxy-ethoxymethoxy)-phenyl]-1-(3,4,5-trimethoxy-phenyl)-ethanone 在 potassium tert-butylate 、 三乙烯二胺 、 乙酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 9.75h， 以35%的产率得到5-chloro-3-[4-methoxy-3-(2-methoxyethoxymethoxy)phenyl]-2-(3,4,5-trimethoxyphenyl)pyridine
  参考文献：
  名称：

  Heterocyclic and Phenyl Double-Bond-Locked Combretastatin Analogues Possessing Potent Apoptosis-Inducing Activity in HL60 and in MDR Cell Lines

  摘要：

  Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 < 1 muM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.

  DOI：

  10.1021/jm049622b

文献信息

• Heterocyclic and Phenyl Double-Bond-Locked Combretastatin Analogues Possessing Potent Apoptosis-Inducing Activity in HL60 and in MDR Cell Lines
  作者：Daniele Simoni、Giuseppina Grisolia、Giuseppe Giannini、Marinella Roberti、Riccardo Rondanin、Laura Piccagli、Riccardo Baruchello、Marcello Rossi、Romeo Romagnoli、Francesco Paolo Invidiata、Stefania Grimaudo、M. Katherine Jung、Ernest Hamel、Nicola Gebbia、Lucia Crosta、Vincenzo Abbadessa、Antonietta Di Cristina、Luisa Dusonchet、Maria Meli、Manlio Tolomeo

  DOI：10.1021/jm049622b

  日期：2005.2.1

  Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 < 1 muM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.