(E)-5-[2-(2-hydroxyphenyl)-vinyl]-benzene-1,3-diol | 354761-94-7

• 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: (E)-5-[2-(2-hydroxyphenyl)-vinyl]-benzene-1,3-diol
• 英文别名: 2,3',5'-Trihydroxy-trans-stilbene；5-[(E)-2-(2-hydroxyphenyl)ethenyl]benzene-1,3-diol
• CAS: 354761-94-7
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: HMLZOBPIONVHTB-AATRIKPKSA-N

物化性质

• 沸点：
  450.7±14.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E)-5-[2-(2-hydroxyphenyl)-vinyl]-benzene-1,3-diol
  参考文献：
  名称：

  通过TRPA1受体脱敏合成白藜芦醇衍生物作为新的镇痛药

  摘要：

  设计，合成和评估了一系列31种白藜芦醇衍生物，以激活和抑制TRPA1通道。大部分充当白藜芦醇或异硫氰酸烯丙酯（AITC）等TRPA1通道的激活剂和脱敏剂。化合物4z（HUHS029）的抑制活性高于白藜芦醇，IC 50值为16.1μM 。通过全细胞膜片钳记录，在表达TRPA1的HEK293细胞以及大鼠背根神经节神经元中证实了4z对TRPA1的活性。此外，用4z预处理对体内AITC引起的TRPA1相关的疼痛行为表现出镇痛作用。

  DOI：

  10.1016/j.bmcl.2017.05.025

文献信息

• A facile and rapid access to resveratrol derivatives and their radioprotective activity
  作者：Saori Uzura、Emiko Sekine-Suzuki、Ikuo Nakanishi、Motohiro Sonoda、Shinji Tanimori

  DOI：10.1016/j.bmcl.2016.07.018

  日期：2016.8

  A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes

  基于芳基硼酸与苯乙烯的钯催化氧化Heck反应，然后以中等至良好的产率脱甲基，可以轻松快速地获得白藜芦醇衍生物。易于合成一系列具有各种官能团的白藜芦醇衍生物。还已经使用大鼠胸腺细胞评估了合成化合物的放射防护活性。结果表明，一些白藜芦醇衍生物有效地保护了胸腺细胞免受辐射诱导的细胞凋亡。
• Resveratrol Derived Butyrylcholinesterase Inhibitors
  作者：René Csuk、Sabrina Albert、Ralph Kluge、Dieter Ströhl

  DOI：10.1002/ardp.201300051

  日期：2013.7

  (E)‐stilbenes were synthesized by Mizoroki–Heck reactions and tested for their ability to inhibit the enzymes acetyl‐ and butyrylcholinesterase. Several of them are good inhibitors of butyrylcholinesterase; one of them carrying an extra fluorine substituent is a 94‐fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase.

  通过 Mizoroki-Heck 反应合成了新型多羟基化 (E)-二苯乙烯，并测试了它们抑制乙酰胆碱酯酶和丁酰胆碱酯酶的能力。其中一些是丁酰胆碱酯酶的良好抑制剂；其中一种带有额外氟取代基的丁酰胆碱酯酶抑制剂是乙酰胆碱酯酶抑制剂的 94 倍。
• Selective synthesis of the resveratrol analogue 4,4′-dihydroxy-<i>trans</i>-stilbene and stilbenoids modification by fungal peroxygenases
  作者：Carmen Aranda、René Ullrich、Jan Kiebist、Katrin Scheibner、José C. del Río、Martin Hofrichter、Angel T. Martínez、Ana Gutiérrez

  DOI：10.1039/c8cy00272j

  日期：——

  reported to date. In contrast, the peroxygenase from the ascomycete Chaetomium globosum (CglUPO) failed to hydroxylate trans-stilbene at the aromatic ring and instead produced the trans-epoxide in the alkenyl moiety. In addition, stilbenoids such as pinosylvin (Pin) and RSV were tested as substrates for the enzymatic synthesis of RSV from Pin and oxyresveratrol (oxyRSV) from both RSV and Pin. Overall, lower

  这项工作提供了第一个证据来自担子菌的非特异性过氧合酶（不稳定周期轨道）茶树菇（AAE UPO），Coprinopsis孢（R子C ci UPO）和皮rotula（MRO UPO）能的区域选择性催化羟化反式-二苯乙烯至4， 4'-二羟基-反式-二苯乙烯（DHS），一种白藜芦醇（RSV）类似物，最近已显示出其对癌症侵袭和转移的预防作用。使用H 2 O 2作为唯一的底物，与Aae一起测试的三种酶可以实现底物的几乎完全转化（产生DHS）。UPO的总营业额（20万）比Mro UPO（26 000）和r Cci UPO（1400）高得多。动力学研究表明，Aae UPO是最有效的催化二苯乙烯二羟基化的酶，其催化效率（k cat / K m）比Mro UPO和r Cci UPO高一到两个数量级，因此4-羟基二苯乙烯似乎是最有效的酶。迄今为止报告的最佳UPO底物。相比之下，来自子囊壳小球囊壳虫（Cgl UP
• Method and system for effecting changes in pigmented tissue
  申请人：Moazed Kambiz Thomas

  公开号：US20120207809A1

  公开（公告）日：2012-08-16

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are compositions for lightening or darkening the pigmented tissues or treating a pigmented tissue disease.

  本文描述了一种快速和可持续改变虹膜基质黑素细胞中黑色素含量的方法和系统，从而改变眼睛的颜色。还描述了用于使色素组织变浅或变深或治疗色素组织疾病的组合物。
• Synthesis and antiproliferative evaluation of 2-hydroxylated (E)-stilbenes
  作者：Yan Zhang、Mingyun Shen、Sunliang Cui、Tingjun Hou

  DOI：10.1016/j.bmcl.2014.10.009

  日期：2014.12

  A simple synthesis of 2-hydroxylated (E)-stilbenes was accomplished in good yields via oxidative coupling of 2-hydroxystyrenes and arylboronic acids, with Rh(III)-catalyst and Cu(OAc)(2) as oxidant. The antiproliferative evaluation of all the synthesized compounds were assessed on four different human cancer cell lines (Colo-205, MDA-468, HT29, and MGC80-3), and the results showed that several compounds exhibit strong antiproliferative activities (up to IC50 = 35 nM for MGC80-3). (C) 2014 Elsevier Ltd. All rights reserved.