2-(3,4-dimethoxystyryl)pyridine | 18096-99-6

• 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: 2-(3,4-dimethoxystyryl)pyridine
• 英文别名: 2-(3,4-Dimethoxystyryl)pyridin；2-[2-(3,4-Dimethoxyphenyl)ethenyl]pyridine
• CAS: 18096-99-6
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: WGWRQOMPMADMNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxystyryl)pyridine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 2-(3,4-dimethoxyphenethyl)pyridine
  参考文献：
  名称：

  Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

  摘要：

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

  DOI：

  10.1016/j.bmc.2019.04.027
• 作为产物：
  描述：

  3,4-二甲氧基苄氯 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 2-(3,4-dimethoxystyryl)pyridine
  参考文献：
  名称：

  Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

  摘要：

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

  DOI：

  10.1016/j.bmc.2019.04.027

文献信息

• Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines
  作者：Jun‐Jie Tian、Zhao‐Ying Yang、Xin‐Shen Liang、Ning Liu、Chen‐Yu Hu、Xian‐Shuang Tu、Xiang Li、Xiao‐Chen Wang

  DOI：10.1002/anie.202007352

  日期：2020.10.12

  Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate

  在此，我们报道了首次实现了2-乙烯基取代吡啶的高度化学选择性和对映选择性的还原。该反应使用手性螺双环双硼烷作为催化剂，HBpin和酸性酰胺作为还原剂，通过包括1,4-氢硼化的级联过程进行，然后转移氢化二氢吡啶中间体。还原产物中保留的双键可通过简单转化将其转化为天然产物和其他有用的杂环化合物。
• Highly regioselective and stereoselective photodimerization of azine-containing stilbenes in neat condition: An efficient synthesis of novel cyclobutanes with heterocyclic substituents
  作者：Alina E. Saifutiarova、Yuri V. Fedorov、François Maurel、Elena N. Gulakova、Valentina A. Karnoukhova、Olga A. Fedorova

  DOI：10.1016/j.jphotochem.2022.113804

  日期：2022.5

  The corresponding cyclobutane derivatives were synthesized with yields of up to 57%. The efficiency of this photoreaction depends on the nature of the heterocyclic residue and the concentration of heterostilbenes. The mild reaction conditions and the absence of additives facilitate the reaction. This work provides a convenient and gentle method for the preparation of cyclobutanes.

  我们开发了一种可见光促进的分子间 [2 + 2] 环加成反应，该反应含有苯环与 OMe 供体基团和作为受体的 6 元含氮环的杂茋分子，该反应在温和条件下在室温下的水中进行. 相应的环丁烷衍生物的合成产率高达 57%。这种光反应的效率取决于杂环残基的性质和杂芪的浓度。温和的反应条件和无添加剂促进了反应。这项工作为环丁烷的制备提供了一种方便而温和的方法。
• Mechanism of hydride abstraction in the electrocyclic phototransformation of heterostilbene
  作者：Alina E. Saifutiarova、Yury V. Fedorov、Elena E. Gulakova、Olga A. Fedorova

  DOI：10.1016/j.mencom.2022.05.027

  日期：2022.5

  A new mechanism of hydride abstraction in the course of a photochemical electrocyclic reaction of heterostilbene in aqueous solution is reported. The study of electrocyclic transformations of heterostilbenes containing different types of heterocyclic residues revealed that the herein estimated mechanism of hydride abstraction is common for heterostilbene photochemical electrocyclization through the

  报道了异茋在水溶液中的光化学电环反应过程中夺取氢化物的新机理。对含有不同类型杂环残基的杂茋的电环转化的研究表明，本文估计的氢化物提取机制对于通过形成新的 C N 键的杂茋光化学电环化是常见的。
• Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives
  作者：Li Guan、Junting Zhou、Qinghua Lin、Huilin Zhu、Wenyuan Liu、Baolin Liu、Yanbo Zhang、Jie Zhang、Jing Gao、Feng Feng、Wei Qu

  DOI：10.1016/j.bmc.2019.04.027

  日期：2019.6

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.