4-hydroxyl-2′-methoxyl-trans-stilbene | 150809-45-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-hydroxyl-2′-methoxyl-trans-stilbene
• 英文别名: (E)-4'-hydroxy-2''-methoxy-1,2-diarylethene；(E)-1-hydroxy-4-(2-methoxy)styrylbenzene；(E)-4-(2-methoxystyryl)phenol；4'-oxy-2-methoxy-stilbene；4'-Oxy-2-methoxy-stilben；4-[(E)-2-(2-methoxyphenyl)ethenyl]phenol
• CAS: 150809-45-3
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: ISSJAYCUTKFKNL-RMKNXTFCSA-N

物化性质

• 熔点：
  149 °C
• 沸点：
  373.8±11.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxyl-2′-methoxyl-trans-stilbene 在 2,6-二甲基吡啶 、 carbon nitride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以73%的产率得到
  参考文献：
  名称：

  白藜芦醇的好氧氧化偶联及其类似物的介孔石墨化碳氮化物（mpg-C3N4）作为生物启发的催化剂的可见光。

  摘要：

  已经开发了白藜芦醇及其类似物通过介孔石墨氮化碳作为生物启发催化剂在可见光下的首次好氧氧化偶联。用这种方法，以中等至高产率合成了δ-viniferin及其类似物。无金属的条件，可见光的辐射以及理想的氧化剂分子氧使这种偶联反应对环境友好且实用。

  DOI：

  10.1002/chem.201303587
• 作为产物：
  描述：

  2-甲氧基溴苄 在 18-冠醚-6 、 sodium methylate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 4-hydroxyl-2′-methoxyl-trans-stilbene
  参考文献：
  名称：

  Synthesis, Antitumor Evaluation, and Apoptosis-Inducing Activity of Hydroxylated (E)-Stilbenes

  摘要：

  The parallel solution-phase synthesis of a series of 30 monohydroxylated (E)-stilbene analogues is described. In vitro screening revealed low micromolar activity (GI(50)) against the MDA MB 468 breast cancer cell line. Activity in MDA MB 468 cells correlated with the ability to induce apoptosis following drug treatment by the most potent agents in the series, e.g., 5dy and 5jy, an observation further reinforced by AnnexinV-FITC analysis and fluorescence microscopy.

  DOI：

  10.1021/jm049238e

文献信息

• Diarylethenes Display In Vitro Anti-TB Activity and Are Efficient Hits Targeting the Mycobacterium tuberculosis HU Protein
  作者：María Suarez、Jhesua Valencia、Christian Cadena、Raktim Maiti、Chandreyee Datta、Gloria Puerto、José Isaza、Homero San Juan、Valakunja Nagaraja、Juan Guzman

  DOI：10.3390/molecules22081245

  日期：——

  Tuberculosis continues to be a great source of concern in global health because of the large reservoir of humans infected with the bacilli and the appearance of clinical isolates resistant to a wide array of anti-tuberculosis drugs. New drugs with novel mechanisms of action on new targets are urgently required to reduce global tuberculosis burden. Mycobacterium tuberculosis nucleoid associated protein (NAP) HU has been shown to be druggable and essential for the organism’s survival. In this study, four diarylethenes were synthesized using a one-pot decarboxylated Heck-coupling of coumaric acids with iodoanisoles. The prepared compounds 1–4 were tested for their in vitro growth inhibition of M. tuberculosis H37Rv using the spot culture growth inhibition assay, displaying minimum inhibitory concentrations between 9 and 22 µM. Their cytotoxicity against BHK-21 cell line showed half inhibition at concentrations between 98 and 729 µM. The most selective hit (SI = 81), demonstrated inhibition of M. tuberculosis HU protein involved in maintaining bacterial genome architecture.

  结核病仍然是全球健康的一大关注点，这是由于感染了杆菌的人类储存量大，以及出现了对多种抗结核药物临床分离株产生耐药性。迫切需要开发作用机制新颖、针对新目标的新药，以减轻全球结核病负担。结核分枝杆菌核小体相关蛋白（NAP）HU已被证明具有成药性，对生物体的生存至关重要。在本研究中，采用一步脱羧 Heck 偶联反应合成了 4 种二芳基乙烯类化合物，用碘氧化的茴香醚与香豆酸。制备的化合物 1-4 通过点状培养生长抑制试验测试了它们对 M. tuberculosis H37Rv 的体外生长抑制作用，显示出最低抑制浓度在 9 至 22 µM 之间。它们对 BHK-21 细胞系的细胞毒性显示半数抑制浓度在 98 至 729 µM 之间。最具选择性的命中（SI = 81）表现出对涉及维持细菌基因组结构的 M. tuberculosis HU 蛋白的抑制作用。
• Ocular imaging
  申请人：Neuroptix Corporation

  公开号：EP2371272A2

  公开（公告）日：2011-10-05

  A system for performing quasi-elastic light scattering and fluorescent ligand scanning on a subject's eye includes a light source configured to transmit light toward the subject's eye, a lens configured to focus light sent from the source and scattered by the subject's eye, a measurement reflector disposed to receive at least a portion of the focused light and configured to reflect a first portion of the received light, a camera configured and disposed to receive the first portion of the received light and configured to provide indicia of an image corresponding to the first portion of the received light, and a processor coupled to the camera and configured to analyze intensities of light in the image to determine a location of a reference point corresponding to an interface of a portion of the eye.

  一种用于在受试者眼睛上执行准弹性光散射和荧光配体扫描的系统，包括一个光源，配置为向受试者眼睛发射光；一个透镜，配置为聚焦从光源发出并由受试者眼睛散射的光；一个测量反射器，配置为接收至少一部分聚焦光，并配置为反射接收光的第一部分、相机，配置为接收接收光的第一部分，并配置为提供与接收光的第一部分相对应的图像指示；以及处理器，与相机耦合，配置为分析图像中的光强度，以确定与眼睛部分界面相对应的参考点的位置。
• System and method for detecting amyloid proteins
  申请人：Neuroptix Corporation

  公开号：EP2420179A2

  公开（公告）日：2012-02-22

  This invention provides a device and method for detecting an amyloid protein in an eye of a mammal. A method comprises for example illuminating the eye with a light source having at least one of a wavelength property, a polarization property or a combination thereof, each appropriate to produce fluorescence in at least an amyloid-binding compound when the amyloid-binding compound is bound to the amyloid protein, the amyloid-binding compound having been introduced to the eye previously and specifically binding to the amyloid protein indicative of the amyloidogenic disorder; and determining a time decay rate of fluorescence for at least the fluorescence produced by the amyloid-binding compound bound to the amyloid protein, the determining permitting distinguishing of the presence of the amyloid-binding compound bound to the amyloid protein in the eye based on at least the time decay rate.

  本发明提供了一种检测哺乳动物眼睛中淀粉样蛋白的装置和方法。例如，该方法包括用光源照射眼睛，该光源具有波长特性、偏振特性或其组合中的至少一种特性，每种特性都适合在淀粉样蛋白结合化合物与淀粉样蛋白结合时至少在淀粉样蛋白结合化合物中产生荧光，淀粉样蛋白结合化合物先前已被引入眼睛，并与指示淀粉样蛋白生成障碍的淀粉样蛋白特异性结合；确定至少由与淀粉样蛋白结合的淀粉样蛋白结合化合物产生的荧光的时间衰减率，该确定允许根据至少时间衰减率来区分眼睛中是否存在与淀粉样蛋白结合的淀粉样蛋白结合化合物。
• Stoermer; Friemel, Chemische Berichte, 1911, vol. 44, p. 1846
  作者：Stoermer、Friemel

  DOI：——

  日期：——
• Inhibitory effect of cytotoxic stilbenes related to resveratrol on the expression of the VEGF, hTERT and c-Myc genes
  作者：Rosa Martí-Centelles、Eva Falomir、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.ejmech.2015.09.014

  日期：2015.10

  A group of thirty-nine stilbene derivatives, prepared by means of Heck coupling reactions, has been investigated for their cytotoxicity, as well as for their ability to inhibit the production of the vascular endothelial growth factor (VEGF) and the activation of telomerase. The ability of these compounds to inhibit proliferation of two tumoral cell lines (HT-29 and MCF-7) and one non tumoral cell line (HEK-293) was first determined. Subsequently, we determined the capacity of the compounds to inhibit the secretion of VEGF in the aforementioned cell lines and to downregulate the expression of the VEGF, hTERT and c-Myc genes, the two latter involved in the control of the activation of telomerase. One of the synthetic stilbenes, (E)-4-(4-methoxystyryl)aniline, showed strong cytotoxicity and proved able to cause a marked decrease both in the secretion of VEGF and in the expression of the hTERT and c-Myc genes, in all cases at concentrations in the low nanomolar range. (C) 2015 Elsevier Masson SAS. All rights reserved.