吡啶,4-[2-(3,4,5-三甲氧苯基)乙烯基]-,(E)- | 118160-75-1

• 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]-,(E)-
• 英文名称: (E) 3',4',5'-trimethoxy-4-azastilbene
• 英文别名: (E)-1-(4-pyridyl)-2-(3,4,5-trimethoxyphenyl)ethene；4-[2-(3,4,5-Trimethoxy-phenyl)-vinyl]-pyridine；4-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]pyridine
• CAS: 118160-75-1
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: NGJDPYNEVBRZTO-SNAWJCMRSA-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]-,(E)- 、 silver dodecanesulfonate 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Liquid-crystalline, polycatenar complexes of silver(I): dependence of the mesomorphism on the ligand and the anion

  摘要：

  我们合成了几系列聚（烷氧基）斯蒂尔巴索配体，并研究了它们与一些银盐形成的复合物的热行为。大多数复合物的通用公式为[AgL2][X]，其中X为十二烷基硫酸盐（DOS）或三氟甲磺酸盐（OTf），L为聚（烷氧基）斯蒂尔巴索，发现在较宽的温度范围内，这些复合物呈现液晶状态，绝大多数具有低熔点。相态主要由六角柱状（Colh）相的形成主导，在小程度上也有双连续Iad立方相；单调型向列相和层状C相仅在一种结构类型的化合物中被观察到。通过在偏振光学显微镜（POM）下观察其光学纹理，先对这些中间相进行赋名，然后通过X射线衍射（XRD）进行确认。通过差示扫描量热法（DSC）确定了转变的温度和焓。发现中间相的形成强烈依赖于配体的取代模式，即烷氧基链的数量、位置和长度，以及对离子的类型。我们从离子相互作用和疏水性的脂肪链与刚性芳香性中央核心之间的平均界面曲率解释了中间相的形成，这与液晶系统相类比。

  DOI：

  10.1039/a809320b
• 作为产物：
  描述：

  3,4,5-三甲氧基苄氯 以 四氢呋喃 为溶剂， 反应 17.67h， 生成 吡啶,4-[2-(3,4,5-三甲氧苯基)乙烯基]-,(E)-
  参考文献：
  名称：

  吡啶基二苯乙烯的设计、合成和细胞毒活性

  摘要：

  在本研究中，通过 Horner-Wadsworth-Emmons (HWE) 反应制备了三个系列的 35 种基于吡啶的二苯乙烯，包括 10 种新化合物，测定了它们对两种肿瘤的细胞毒活性。

  DOI：

  10.1080/14786419.2023.2227991

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.
• Lapucha, Andrzej R., Polish Journal of Chemistry, 1987, vol. 61, # 4-6, p. 563 - 567
  作者：Lapucha, Andrzej R.

  DOI：——

  日期：——
• STYRYL SULFIDE DYES
  申请人：BASF SE

  公开号：EP3041904B1

  公开（公告）日：2020-05-20
• US5358999A
  申请人：——

  公开号：US5358999A

  公开（公告）日：1994-10-25
• US5330877A
  申请人：——

  公开号：US5330877A

  公开（公告）日：1994-07-19