4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide | 134029-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide
• CAS: 134029-82-6
• 化学式: C₁₇H₁₉NO₅
• 分子量: 317.342
• InChiKey: WUVXRJAWUCTARA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 3,4,5-trimethoxy-N-(4-methoxybenzyl)aniline
  参考文献：
  名称：

  具有萘部分的新型磺酰胺衍生物作为有效微管蛋白聚合抑制剂的合成、生物学评价和分子对接研究

  摘要：

  摘要 合成了一系列带有萘部分的新磺酰胺衍生物，并评估了它们的抗增殖和微管蛋白聚合抑制活性。使用CCK-8方法评估了这些新化合物对MCF-7和A549的体外抗增殖活性。在所有测试的化合物中，具有萘-1-基部分的化合物5c对 MCF-7 和 A549 细胞系表现出最有效的抗增殖活性，IC 50值分别为 0.51 ± 0.03 µM 和 0.33 ± 0.01 µM。微管蛋白聚合试验的结果表明，5c表现出显着的抑制微管蛋白聚合的能力，IC 50值为 2.8 μM。与其抗微管蛋白活性一致，5c可以显着阻止 G2/M 期的细胞周期并诱导 MCF-7 癌细胞凋亡。分子对接研究表明，化合物5c通过在微管蛋白的秋水仙碱结合位点相互作用来抑制微管蛋白聚合。此外，5c对人类正常细胞系表现出低细胞毒活性。

  DOI：

  10.1080/14756366.2021.1943378
• 作为产物：
  描述：

  大茴香酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  RhIII 催化酰胺的 CH 烯丙基化和 3,4-二氢异喹啉-1(2H)-酮与 N-溴代琥珀酰亚胺的多米诺环合成

  摘要：

  用烯丙基溴在室温下开发了 RhIII 催化的缺电子芳烃、杂芳烃和烯烃的 C-H 烯丙基化反应。反应在乙醚中进行，不脱水，苯胺衍生酰胺的导向阴离子氮有助于 C-H 活化。在烯丙基化之后，通过引入的双键的分子内氨基溴化，实现了 3,4-二氢异喹啉-1(2H)-酮与 N-溴代琥珀酰亚胺 (NBS) 的多米诺循环合成。

  DOI：

  10.1002/ejoc.201501551

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.
• Novel diarylamides and diarylureas with N-substitution dependent activity against medulloblastoma
  作者：Christopher Lawson、Thowaiba Babikr Ahmed Alta、Georgia Moschou、Vasiliki Skamnaki、Theodora G.A. Solovou、Caroline Topham、Joseph Hayes、Timothy J. Snape

  DOI：10.1016/j.ejmech.2021.113751

  日期：2021.12
• STILBENE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Research Corporation Technologies, Inc.

  公开号：EP0641301A1

  公开（公告）日：1995-03-08
• 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.