N-(4-methoxyphenyl)-3,5-dimethoxybenzamide | 134029-83-7

• 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: N-(4-methoxyphenyl)-3,5-dimethoxybenzamide
• 英文别名: N-(p-methoxyphenyl)-3,5-dimethoxybenzamide；3,5-Dimethoxy-N-(4-Methoxyphenyl)Benzamide
• CAS: 134029-83-7
• 化学式: C₁₆H₁₇NO₄
• mdl: MFCD00754697
• 分子量: 287.315
• InChiKey: NGIDRYCBDLWOSR-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±42.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 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：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-3,5-dimethoxybenzamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-(3,5-dimethoxybenzyl)-4-methoxybenzenamine
  参考文献：
  名称：

  Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization

  摘要：

  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.

  DOI：

  10.1021/jm00112a036
• 作为产物：
  描述：

  甲氧苯胺 、 3,5-二甲氧基苯甲酸 在 三氯乙腈 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以56.2%的产率得到N-(4-methoxyphenyl)-3,5-dimethoxybenzamide
  参考文献：
  名称：

  白藜芦醇衍生物对前列腺癌细胞进展的有效抑制作用

  摘要：

  在各种研究中，白藜芦醇已被确定为一种有效的抗癌剂。在这项研究中，合成并研究了几种白藜芦醇衍生物，以寻找比白藜芦醇更有效的抗癌剂。在我们对癌细胞系的检查期间，化合物 C、F 和 G 在 PC-3 和 LNCaP 人前列腺癌细胞的生长方面表现出比白藜芦醇更高的抑制活性。此外，白藜芦醇的四种衍生物在 LNCaP 细胞中显示出有效的生长抑制活性 (IC50 0.01 ～ 0.04 μM)。这些衍生物的活性水平是与白藜芦醇相关的活性水平的 25-100 倍（IC50 1.0 μM）。我们的结果表明，化合物 C、D、F 和 G 可能作为前列腺肿瘤的抗癌剂发挥作用。

  DOI：

  10.1002/ardp.200500228

文献信息

• Synthesis of heterocycle-based analogs of resveratrol and their antitumor and vasorelaxing properties
  作者：Simone Bertini、Vincenzo Calderone、Isabella Carboni、Roberta Maffei、Alma Martelli、Adriano Martinelli、Filippo Minutolo、Mehdi Rajabi、Lara Testai、Tiziano Tuccinardi、Riccardo Ghidoni、Marco Macchia

  DOI：10.1016/j.bmc.2010.07.059

  日期：2010.9

  New resveratrol (RES) analogs were developed by replacing the aromatic ‘core’ of our initial naphthalene-based RES analogs with pseudo-heterocyclic (salicylaldoxime) or heterocyclic (benzofuran, quinoline, and benzothiazole) scaffolds. The resulting analogs were tested for their antiproliferative and vasorelaxing effect, two typical properties shown by RES. Some of the new compounds confirmed strong

  通过用假杂环（水杨醛肟）或杂环（苯并呋喃，喹啉和苯并噻唑）支架取代我们最初的萘基RES类似物的芳族“核心”，开发了新的白藜芦醇（RES）类似物。测试了所得类似物的抗增殖和血管松弛作用，这是RES显示的两个典型特性。一些新化合物证实了很强的抗增殖活性，可与以前以最具活性的萘基类似物发现的抗坏血酸相媲美。特别地，3-（3,5-二羟基苯基）-7-羟基喹啉表现出最有效的抗增殖作用（IC 50  = 17.4μM）。在血管测定中，最高效力（pIC 50  = 4.92）和功效（E max 用2-（3，5-二羟基苯基）-6-羟基苯并噻唑获得＝（88.2％）。这些化合物的构象分析表明，对MDA-MB-231癌细胞的抗增殖活性可能与活性最高的化合物的共同空间分布有关，尤其是与三个酚基的空间排列有关。此外，血管松弛性质与通过静电分子电势（ESP）测得的电子性质具有良好的相关性。
• Nickel-catalyzed C–H/N–H annulation of aromatic amides with alkynes in the absence of a specific chelation system
  作者：Atsushi Obata、Yusuke Ano、Naoto Chatani

  DOI：10.1039/c7sc01750b

  日期：——

  of KOBut involves C–H/N–H oxidative annulation to give 1(2H)-isoquinolinones. A key to the success of the reaction is the use of a catalytic amount of strong base, such as KOBut. The reaction shows a high functional group compatibility. The reaction with unsymmetrical alkynes, such as 1-arylalkynes, gives the corresponding 1(2H)-isoquinolinones with a high level of regioselectivity. This discovery would

  具有在甲部存在炔芳族酰胺的Ni基催化的反应吨涉及C-H / N-H的氧化环，得到1-（2 ħ）异喹啉酮。反应成功的关键是使用催化量的强碱，例如KOBu t。该反应显示出高的官能团相容性。与不对称炔烃，例如1-芳基炔烃的反应，得到具有高区域选择性的相应的1（2 H）-异喹啉酮。这一发现将导致开发镍催化的螯合辅助的C–H功能化反应，而无需特定的螯合系统。
• 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.
• Potent Inhibitory Effects of Resveratrol Derivatives on Progression of Prostate Cancer Cells
  作者：Kyung Mi Yoo、Sanghee Kim、Bo Kyung Moon、Sung Soo Kim、Kyung Tack Kim、Sun Yeou Kim、Sang Yoon Choi

  DOI：10.1002/ardp.200500228

  日期：2006.5

  and LNCaP human prostate cancer cells. Moreover, four derivatives of resveratrol evidenced potent growth inhibitory activity (IC50 0.01 ˜ 0.04 μM) in LNCaP cells. The levels of activity in these derivatives were 25 ˜ 100 times stronger than that associated with resveratrol (IC50 1.0 μM). Our results suggested that compounds C, D, F, and G might function as anticancer agents on prostate tumors. This study

  在各种研究中，白藜芦醇已被确定为一种有效的抗癌剂。在这项研究中，合成并研究了几种白藜芦醇衍生物，以寻找比白藜芦醇更有效的抗癌剂。在我们对癌细胞系的检查期间，化合物 C、F 和 G 在 PC-3 和 LNCaP 人前列腺癌细胞的生长方面表现出比白藜芦醇更高的抑制活性。此外，白藜芦醇的四种衍生物在 LNCaP 细胞中显示出有效的生长抑制活性 (IC50 0.01 ～ 0.04 μM)。这些衍生物的活性水平是与白藜芦醇相关的活性水平的 25-100 倍（IC50 1.0 μM）。我们的结果表明，化合物 C、D、F 和 G 可能作为前列腺肿瘤的抗癌剂发挥作用。