吡啶,4-[2-(3,4,5-三甲氧苯基)乙烯基]-,(Z)- | 134029-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 吡啶,4-[2-(3,4,5-三甲氧苯基)乙烯基]-,(Z)-
• 英文名称: (Z)-1-(4-Pyridyl)-2-(3,4,5-trimethoxyphenyl)ethene
• 英文别名: (Z) 4-[2-(3,4-Trimethoxyphenyl)ethenyl]pyridine；4-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]pyridine
• CAS: 134029-54-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: NGJDPYNEVBRZTO-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡啶,4-[2-(3,4,5-三甲氧苯基)乙烯基]-,(Z)- 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以92%的产率得到4-[(Z)-2-(3,4,5-Trimethoxy-phenyl)-vinyl]-pyridine 1-oxide
  参考文献：
  名称：

  Novel B-ring modified combretastatin analogues: Syntheses and antineoplastic activity

  摘要：

  A series of B-ring modified combretastatin analogues were synthesized and their inhibitory activity against microtubule assembly, cytotoxic activity against Colon 26 adenocarcinoma cancer cell line were evaluated. Among these, pyridone derivative (19) showed strong antimitotic activity and cytotoxicity, along with excellent water-solubility. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00622-2
• 作为产物：
  描述：

  4-吡啶甲醛 、 三苯基-(3,4,5-三甲氧基-苄基)-溴化膦 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以50%的产率得到吡啶,4-[2-(3,4,5-三甲氧苯基)乙烯基]-,(Z)-
  参考文献：
  名称：

  Novel B-ring modified combretastatin analogues: Syntheses and antineoplastic activity

  摘要：

  A series of B-ring modified combretastatin analogues were synthesized and their inhibitory activity against microtubule assembly, cytotoxic activity against Colon 26 adenocarcinoma cancer cell line were evaluated. Among these, pyridone derivative (19) showed strong antimitotic activity and cytotoxicity, along with excellent water-solubility. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00622-2

文献信息

• Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Asit K. Chakraborti、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00112a036

  日期：1991.8

  An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitors of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene (5a). This substance was almost as potent as combretastatin A-4 (1a), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (1a), dihydrocombretastatin A-4 (1c), and trans-combretastatin A-4 (1b). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.
• US5430062A
  申请人：——

  公开号：US5430062A

  公开（公告）日：1995-07-04
• [EN] STILBENE DERIVATIVES AS ANTICANCER AGENTS<br/>[FR] DERIVES DE STILBENE UTILISES COMME AGENTS ANTICANCEREUX
  申请人：——

  公开号：WO1993023357A1

  公开（公告）日：1993-11-25

  [EN] The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds amont those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.
  [FR] Dérivés de stilbène présentant une utilité comme agents anticancéreux. On peut utiliser lesdits composés afin de traiter des cancers susceptibles d'être traités avec ceux-ci, et dans un procédé de traitement desdits cancers. L'invention concerne également des compositions pharmaceutiques contenant lesdits composés. Les composés préférés parmi ceux décrits dans l'invention sont (Z)-1-(4-méthoxyphényl)-2-(3,4,5-triméthoxyphényl)éthène, (Z)-1-(4-méthylphényl)-2-(3,4,5-triméthoxyphényl)éthène, et l'hydrochlorate de 4-méthyl-3',4',5'-triméthoxybenzylaniline.