3-(2,3-dimethoxyphenoxy)propanoic acid | 64139-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2,3-dimethoxyphenoxy)propanoic acid
• CAS: 64139-40-8
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: PXQHZXQKAJNGEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  329.9±27.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  3-(2,3-dimethoxyphenoxy)propanoic acid 在 pyridinium hydrobromide perbromide 、 四磷十氧化物 作用下， 以 乙醇 、 氯仿 、 苯 为溶剂， 反应 4.67h， 生成 3-bromo-7,8-dimethoxy-2,3-dihydrochromen-4-one
  参考文献：
  名称：

  Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction

  摘要：

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.

  DOI：

  10.1021/jm401733v
• 作为产物：
  描述：

  3-氯丙酸 、 2,3-二甲氧基苯酚 在 氢氧化钾 作用下， 生成 3-(2,3-dimethoxyphenoxy)propanoic acid
  参考文献：
  名称：

  Pfeiffer; Haack; Willems, Chemische Berichte, 1928, vol. 61, p. 298

  摘要：

  DOI：

文献信息

• The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae (<i>sensu</i> APGII)
  作者：Sianne Schwikkard、Hannah Whitmore、Kamakshi Sishtla、Rania S. Sulaiman、Trupti Shetty、Halesha D. Basavarajappa、Catherine Waller、Alaa Alqahtani、Lennart Frankemoelle、Andy Chapman、Neil Crouch、Wolfgang Wetschnig、Walter Knirsch、Jacky Andriantiana、Eduard Mas-Claret、Moses K. Langat、Dulcie Mulholland、Timothy W. Corson

  DOI：10.1021/acs.jnatprod.8b00989

  日期：2019.5.24

  of a group of naturally occurring homoisoflavonoids isolated from the family Hyacinthaceae and related synthetic compounds, chosen for synthesis based on structure-activity relationship observations. Several compounds showed interesting antiproliferative and antiangiogenic activities in vitro on retinal microvascular endothelial cells, a disease-relevant cell type, with the synthetic chromane, 46,

  眼睛中过多的血管形成与湿性年龄相关性黄斑变性、增殖性糖尿病视网膜病变、新生血管性青光眼和早产儿视网膜病变有关，这些都是导致失明的主要原因。迫切需要小分子抗血管生成药物来补充现有的生物制剂。先前已证明同异黄酮类化合物在内皮细胞中比其他细胞类型具有更有效的抗增殖活性。此外，它们在体外和体内的眼新生血管动物模型中表现出强大的抗血管生成潜力。在这里，我们测试了一组从风信子科中分离出来的天然同型异黄酮类化合物和相关合成化合物的抗血管生成活性，这些化合物是根据结构-活性关系观察选择进行合成的。几种化合物在体外对视网膜微血管内皮细胞（一种与疾病相关的细胞类型）显示出有趣的抗增殖和抗血管生成活性，其中合成苯并二氢吡喃 46 显示出最佳活性（GI50 为 2.3 × 10-4 μM）。
• Pfeiffer; Oberlin; Konermann, Chemische Berichte, 1925, vol. 58, p. 1955
  作者：Pfeiffer、Oberlin、Konermann

  DOI：——

  日期：——
• Anti-inflammatory activities of selected synthetic homoisoflavanones
  作者：Mahidansha M. Shaikh、Hendrik G. Kruger、Johannes Bodenstein、Peter Smith、Karen du Toit

  DOI：10.1080/14786419.2011.565004

  日期：2012.8

  Four homoisoflavanones of the 3-benzylidene-4-chromanone type, some of which were previously isolated from Caesalpinia pulcherrima, were synthesised to determine their anti-inflammatory activity and cytotoxicity. A range of four different homoisoflavanones (compounds 4a-4d) were synthesised from the corresponding substituted phenols. H-1- and C-13-NMR data together with high-resolution mass spectroscopy data were employed to elucidate the structures. Anti-inflammatory activity was determined in mice with acute croton oil-induced auricular dermatitis. In vitro cytotoxicity was tested against a Chinese hamster ovarian cell line using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide (MTT) assay. Compound 4a exhibited a tendency to inhibit oedema in a dose-dependent manner after 3 and 6 h of treatment. Compounds 4b-4d also inhibited oedema, although a clear dose-response relationship was not observed. Compounds 4a-4c were found to be less cytotoxic than compound 4d. Compound 4b was the least cytotoxic. Compounds 4a-4d exhibited anti-inflammatory activity and varying levels of cytotoxicity.
• Synthesis of Rigidified eIF4E/eIF4G Inhibitor-1 (4EGI-1) Mimetic and Their in Vitro Characterization as Inhibitors of Protein–Protein Interaction
  作者：Poornachandran Mahalingam、Khuloud Takrouri、Ting Chen、Rupam Sahoo、Evangelos Papadopoulos、Limo Chen、Gerhard Wagner、Bertal H. Aktas、Jose A. Halperin、Michael Chorev

  DOI：10.1021/jm401733v

  日期：2014.6.26

  The 4EGI-1 is the prototypic inhibitor of eIF4E/eIF4G interaction, a potent inhibitor of translation initiation in vitro and in vivo and an efficacious anticancer agent in animal models of human cancers. We report on the design, synthesis, and in vitro characterization of a series of rigidified mimetic of this prototypic inhibitor in which the phenyl in the 2-(4-(3,4-dichlorophenyl)thiazol-2-yl) moiety was bridged into a tricyclic system. The bridge consisted one of the following: ethylene, methylene oxide, methylenesulfide, methylenesulfoxide, and methylenesulfone. Numerous analogues in this series were found to be markedly more potent than the parent prototypic inhibitor in the inhibition of eIF4E/eIF4G interaction, thus preventing the eIF4F complex formation, a rate limiting step in the translation initiation cascade in eukaryotes, and in inhibition of human cancer cell proliferation.
• Pfeiffer; Haack; Willems, Chemische Berichte, 1928, vol. 61, p. 298
  作者：Pfeiffer、Haack、Willems

  DOI：——

  日期：——