3-(methoxymethoxy)-1-ethynylbenzene | 1261074-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(methoxymethoxy)-1-ethynylbenzene
• 英文别名: 1-Ethynyl-3-(methoxymethoxy)benzene；1-ethynyl-3-(methoxymethoxy)benzene
• CAS: 1261074-36-5
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: XBVDTXGVOCCWHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(methoxymethoxy)-1-ethynylbenzene 在 盐酸 、 苯基脲 、 氢气 、 sodium methylate 、 palladium diacetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~110.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 生成 (E,E)-1-(3-hydroxystyryl)-4-(3,4-dihydroxystyryl)benzene
  参考文献：
  名称：

  Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers

  摘要：

  Starting from bisphenolic bis-styrylbenzene DF-9 (4), P-amyloid (A beta) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with beta-amyloid peptide A beta(1-40) and a fluorescence assay using APP/PSI transgenic mouse brain sections. Bis-styrylbenzene SA R is derived largely from work on symmetrical compounds. This study is the first to describe A beta binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an A beta binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood brain barrier and bound to A beta plaques in vivo. By use of a DPPH assay, phenol functional groups with papa orientations seem to be a necessary. but insufficient, criterion for good free radical scavenging properties in these compounds.

  DOI：

  10.1021/jm1006929
• 作为产物：
  描述：

  1-iodo-3-(methoxymethoxy)benzene 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 3-(methoxymethoxy)-1-ethynylbenzene
  参考文献：
  名称：

  Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers

  摘要：

  Starting from bisphenolic bis-styrylbenzene DF-9 (4), P-amyloid (A beta) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with beta-amyloid peptide A beta(1-40) and a fluorescence assay using APP/PSI transgenic mouse brain sections. Bis-styrylbenzene SA R is derived largely from work on symmetrical compounds. This study is the first to describe A beta binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an A beta binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood brain barrier and bound to A beta plaques in vivo. By use of a DPPH assay, phenol functional groups with papa orientations seem to be a necessary. but insufficient, criterion for good free radical scavenging properties in these compounds.

  DOI：

  10.1021/jm1006929

文献信息

• Potent Antitumor Mimetics of Annonaceous Acetogenins Embedded with an Aromatic Moiety in the Left Hydrocarbon Chain Part
  作者：Qicai Xiao、Yongqiang Liu、Yatao Qiu、Guangbiao Zhou、Chan Mao、Zheng Li、Zhu-Jun Yao、Sheng Jiang

  DOI：10.1021/jm101053k

  日期：2011.1.27

  Annonaceous acetogenins are a large family of naturally occurring polyketides exhibiting remarkable anticancer activities. The first generation of annonaceous acetogenin mimetic (1, AA005) exhibits comparable activity as that of natural products and presents much higher selectivity between cancer and normal cells. In this work, we report the design, synthesis, and evaluation of a new series of compound

  丙酮酸非生成素是一大类天然聚酮化合物，表现出显着的抗癌活性。第一代非丙酮产乙酸原素模拟物（1，AA005）具有与天然产物相当的活性，并且在癌症细胞与正常细胞之间具有更高的选择性。在这项工作中，我们报告了一系列新的化合物1类似物的设计，合成和评估，在这些化合物中，各种构象受限的片段嵌入了左侧的烃链部分。已鉴定出具有联苯部分的化合物7具有更强的抗增殖活性，并且比正常细胞优先靶向癌细胞，因此代表了进一步优化的新线索。
• Ailanthoidol Derivatives and their Anti-inflammatory Effects
  作者：Na-Li Lee、Jae-Jun Lee、Jin-Kyung Kim、Jong-Gab Jun

  DOI：10.5012/bkcs.2012.33.6.1907

  日期：2012.6.20

  Ailanthoidol showed a strong $anti$-inflammatory effect in a previous result. Ailanthoidol derivatives were prepared for the $anti$-inflammatory test using Sonogashira coupling, iodine induced cyclization and Wittig reaction. $Anti$-inflammatory effects of the prepared ailanthoidol derivatives were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that some ailanthoidol derivatives inhibited significantly the production of inflammatory mediator nitric oxide.

  Ailanthoidol在之前的实验中表现出强烈的抗炎效果。使用SonogashiRA耦合、碘诱导环化和Wittig反应合成了Ailanthoidol衍生物，用于抗炎测试。对制备的Ailanthoidol衍生物的抗炎效果在脂多糖（LPS）刺激的RAW 264-7巨噬细胞中进行了检查。结果显示，某些Ailanthoidol衍生物显著抑制了炎症介质一氧化氮的产生。
• Compositions and methods for glucose transport inhibition
  申请人：OHIO UNIVERSITY

  公开号：US10000443B2

  公开（公告）日：2018-06-19

  Glucose deprivation is an attractive strategy in cancer research and treatment. Cancer cells upregulate glucose uptake and metabolism for maintaining accelerated growth and proliferation rates. Specifically blocking these processes is likely to provide new insights to the role of glucose transport and metabolism in tumorigenesis, as well as in apoptosis. As solid tumors outgrow the surrounding vasculature, they encounter microenvironments with a limited supply of nutrients leading to a glucose deprived environment in some regions of the tumor. Cancer cells living in the glucose deprived environment undergo changes to prevent glucose deprivation-induced apoptosis. Knowing how cancer cells evade apoptosis induction is also likely to yield valuable information and knowledge of how to overcome the resistance to apoptosis induction in cancer cells. Disclosed herein are novel anticancer compounds that inhibit basal glucose transport, resulting in tumor suppression and new methods for the study of glucose deprivation in animal cancer research.

  在癌症研究和治疗中，葡萄糖剥夺是一种极具吸引力的策略。癌细胞会上调葡萄糖摄取和新陈代谢，以维持加速生长和增殖速度。专门阻断这些过程有可能为了解葡萄糖转运和代谢在肿瘤发生和凋亡中的作用提供新的视角。随着实体瘤向周围血管外生长，它们会遇到营养供应有限的微环境，导致肿瘤的某些区域出现葡萄糖匮乏的环境。生活在葡萄糖匮乏环境中的癌细胞会发生变化，以防止葡萄糖匮乏诱导的细胞凋亡。了解癌细胞如何逃避凋亡诱导，还可能获得关于如何克服癌细胞对凋亡诱导的抗性的有价值的信息和知识。本文公开了新型抗癌化合物，这些化合物可抑制基础葡萄糖转运，从而抑制肿瘤，还公开了在动物癌症研究中研究葡萄糖剥夺的新方法。
• Novel Stereo‐Induction Pattern in Pudovik Addition/Phospha‐Brook Rearrangement Towards Chiral Trisubstituted Allenes
  作者：Jia‐Yan Zheng、Fan Wang、Yan Zhang、Zheng Zheng、Jia‐Hong Wu、Xiaoyu Ren、Zhishan Su、Wenchuan Chen、Tianli Wang

  DOI：10.1002/anie.202403707

  日期：2024.5.27

  developed to synthesize axially chiral phosphorus allenes through a PPS-catalyzed asymmetric Pudovik addition followed by phospha-Brook rearrangement. Mechanistic experiments have demonstrated that the enantio-determining step is the 1,2-addition, with the subsequent rearrangement undergoing a central-to-axial chirality transfer.

  我们开发了一种有效且实用的方法，通过 PPS 催化的不对称 Pudovik 加成，然后进行磷-布鲁克重排来合成轴向手性磷丙二烯。机理实验表明，对映体决定步骤是 1,2-加成，随后的重排经历中心到轴的手性转移。
• COMPOSITIONS AND METHODS FOR GLUCOSE TRANSPORT INHIBITION
  申请人：Chen Xiaozhuo

  公开号：US20120121536A1

  公开（公告）日：2012-05-17

  Glucose deprivation is an attractive strategy in cancer research and treatment. Cancer cells upregulate glucose uptake and metabolism for maintaining accelerated growth and proliferation rates. Specifically blocking these processes is likely to provide new insights to the role of glucose transport and metabolism in tumorigenesis, as well as in apoptosis. As solid tumors outgrow the surrounding vasculature, they encounter microenvironments with a limited supply of nutrients leading to a glucose deprived environment in some regions of the tumor. Cancer cells living in the glucose deprived environment undergo changes to prevent glucose deprivation-induced apoptosis. Knowing how cancer cells evade apoptosis induction is also likely to yield valuable information and knowledge of how to overcome the resistance to apoptosis induction in cancer cells. Disclosed herein are novel anticancer compounds that inhibit basal glucose transport, resulting in tumor suppression and new methods for the study of glucose deprivation in animal cancer research.