顺式-3,4',5-三甲氧基-3'-羟基二苯乙烯 | 586410-08-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 顺式-3,4',5-三甲氧基-3'-羟基二苯乙烯
• 中文别名: 顺式3,4',5-三甲氧基-3'-羟基二苯乙烯；顺式3,4',5 - 三甲氧基-3' - 羟基二苯乙烯
• 英文名称: cis-3,4',5-trimethoxy-3'-hydroxystilbene
• 英文别名: 5-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]-2-methoxyphenol
• CAS: 586410-08-4
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: UQIWTPQGJCCTPA-PLNGDYQASA-N

物化性质

• 熔点：
  N /A
• 沸点：
  472.8±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  顺式-3,4',5-三甲氧基-3'-羟基二苯乙烯 在 三氯氧磷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 生成
  参考文献：
  名称：

  一种芳氧基磷酸酯单钠盐的制备及应用

  摘要：

  本发明公开了一种芳氧基磷酸酯单钠盐的制备方法及应用，其制备步骤是在有机溶剂中，以取代的酚类化合物为原料，在三氯氧磷及碱存在下，在冰水浴中进行磷酰基化反应和碱化反应，反应完成后加入水，搅拌、萃取、干燥、减压浓缩，得到酚的磷酰基化产物；然后滴加NaOH溶液以析出白色沉淀，然后冷却、抽滤、水洗、丙酮泡洗、干燥，得到芳氧基磷酸酯单钠盐。进一步，采用芳氧基磷酸酯单钠盐制备芳氧基磷酸酯二钠盐、芳氧基磷酸二氢酯及芳氧基磷酸酯盐。本发明具有后处理简洁高效、收率高、适合规模化制备的优点。

  公开号：

  CN106146548B
• 作为产物：
  描述：

  3,5-二甲氧基溴苄 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.0h， 生成 顺式-3,4',5-三甲氧基-3'-羟基二苯乙烯
  参考文献：
  名称：

  Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers

  摘要：

  New carbon-11 and fluorine-18 labeled stilbene derivatives, cis-3,5-dimethoxy-4'-[C-11]methoxystilbene (4'-[C-11]8a), cis-3,4',5-trimethoxy-3'-[C-11]methoxystilbene (3'-[C-11]8b), trans-3,5-dimethoxy-4'-[C-11]methoxystilbene (4'-[C-11]10a), trans-3,4',5-trirnethoxy-3'-[C-11]methoxystilbene (3'-[C-11]10b), cis- 3,5-dimethoxy-4'-[F-18]fluorostilbene (4'-[F-18]12a), and trans-3,5-dimethoxy-4'-[F-18]fluorostilbene (4'-[F-18]13a), were designed and synthesized as potential PET probes for aryl hydrocarbon receptor (AhR) in cancers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.088

文献信息

• STILBENE DERIVATIVES AS NEW CANCER THERAPEUTIC AGENTS
  申请人：Lee Ruey-min

  公开号：US20080261982A1

  公开（公告）日：2008-10-23

  Stilbene derivatives exhibit killing and suppression of growth activity against a variety of cancer cells, and are effective at suppressing tumor growth in vivo. The stilbene derivatives may be used in the treatment of diseases characterized by cell hyperproliferation including human malignancies and non-malignant diseases such as liver cirrhosis. Stilbenes may also disrupt abnormal vessels in tumor to achieve vascular disrupting effect to suppress tumor growth. Water soluble pro-drug forms of stilbene derivatives are particularly useful in suppressing tumor growth in vivo.

  Stilbene衍生物表现出对多种癌细胞的杀灭和抑制生长活性，并且在体内有效地抑制肿瘤生长。Stilbene衍生物可用于治疗以细胞过度增殖为特征的疾病，包括人类恶性肿瘤和非恶性疾病，如肝硬化。Stilbenes也可以破坏肿瘤中的异常血管，实现血管破坏效应以抑制肿瘤生长。水溶性的Stilbene衍生物前药形式在体内抑制肿瘤生长方面特别有用。
• CuI/1,10-phen/PEG promoted decarboxylation of 2,3-diarylacrylic acids: synthesis of stilbenes under neutral and microwave conditions with an in situ generated recyclable catalyst
  作者：Yong Zou、Qi Huang、Tong-kun Huang、Qing-chun Ni、En-sheng Zhang、Tian-long Xu、Mu Yuan、Jun Li

  DOI：10.1039/c3ob41588k

  日期：——

  A series of trans- or cis-stilbenes have been synthesized in good to excellent yields via a functional group-dependent decarboxylation process from the corresponding 2,3-diaryl acrylic acids in a neutral CuI/1,10-phen/PEG-400 system under microwave conditions. The in situ generation of the recyclable catalytic complex, the use of environmentally benign solvent PEG-400, the operational simplicity, the short reaction times, as well as the functional group-dependent chemo- and stereo-selectivity have made the decarboxylation process a highly efficient and applicable protocol.

  在中性 CuI/1,10-phen/PEG-400 体系中，通过官能团依赖性脱羧过程，从相应的 2,3-二芳基丙烯酸中合成了一系列反式或顺式二苯乙烯，收率良好至优异在微波条件下。可回收催化复合物的原位生成、环境友好溶剂 PEG-400 的使用、操作简单、反应时间短以及官能团依赖性化学和立体选择性使得脱羧过程成为高度高效且适用的协议。
• Methods and compositions for treatment of cancer and autoimmune disease
  申请人：THE JACKSON LABORATORY

  公开号：US10207988B2

  公开（公告）日：2019-02-19

  The technology described herein relates to methods of inducing cell death. The technology described herein further relates to treating conditions including cancers and autoimmune diseases comprising administering inhibitors of double strand break repair. Also described herein are inhibitors of double strand break repair and methods of screening for such inhibitors.

  本文所述技术涉及诱导细胞死亡的方法。本文所述技术还涉及通过施用双链断裂修复抑制剂来治疗包括癌症和自身免疫性疾病在内的疾病。本文还描述了双链断裂修复抑制剂和筛选此类抑制剂的方法。
• Compositions and methods for immune-mediated cancer therapy
  申请人：Teclison Limited

  公开号：US11534445B2

  公开（公告）日：2022-12-27

  Disclosed herein are methods and compositions for enhancing an immune response to a solid tumor in a subject. In some embodiments, a method comprises: (a) administering to the subject a hypoxia-activated bioreductive agent (HABA); (b) inducing hypoxia by (i) administering a hypoxia-inducing agent to the subject or (ii) embolizing one or more blood vessels supplying the solid tumor; and (c) administering an immune checkpoint inhibitor prior to, simultaneously with, or subsequent to step (b) in an amount effective to enhance an immune response to the solid tumor, as compared to an immune response in the absence of the immune checkpoint inhibitor. Kits for use in the disclosed methods are also provided.

  本文公开了用于增强受试者对实体瘤的免疫应答的方法和组合物。在一些实施方案中，方法包括(a) 向受试者施用缺氧激活的生物还原剂（HABA）；(b) 通过(i)向受试者施用缺氧诱导剂或(ii)栓塞供应实体瘤的一个或多个血管来诱导缺氧；以及(c)在步骤(b)之前、同时或之后施用免疫检查点抑制剂，施用量有效于增强对实体瘤的免疫应答，与不施用免疫检查点抑制剂时的免疫应答相比。还提供了用于所公开方法的试剂盒。
• Design, synthesis and biological evaluation of novel stilbene-based antitumor agents
  作者：Daniele Simoni、Francesco Paolo Invidiata、Marco Eleopra、Paolo Marchetti、Riccardo Rondanin、Riccardo Baruchello、Giuseppina Grisolia、Ashutosh Tripathi、Glen E. Kellogg、David Durrant、Ray M. Lee

  DOI：10.1016/j.bmc.2008.12.002

  日期：2009.1

  A series of novel stilbene derivatives has been synthesized and studied with the main goal to investigate SAR of the amino compound 1a, as well as to improve its water solubility, a potentially negative aspect of the molecule that could be a serious obstacle for a pre-clinical development. We have obtained derivatives with good cytotoxic activity, in particular, the derivatives 5c and 6b could represent two novel leads for further investigation. Compound 8b, a morpholino-carbamate derivative, prodrug of 1a, has a very good solubility in water, and is active in suppressing growth of tumor cells at a concentration of 5000 nM, which is a concentration 100 times higher than the parent stilbene 1a. (C) 2008 Elsevier Ltd. All rights reserved.