(E)-3-(4-(methoxymethoxy)phenyl)acrylic acid | 61844-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-(methoxymethoxy)phenyl)acrylic acid
• 英文别名: (E)-3-[4-(methoxymethoxy)phenyl]acrylic acid；(E)-3-[4-(methoxymethoxy)phenyl]prop-2-enoic acid
• CAS: 61844-66-4
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: NRAGMSQWKTWPIL-QPJJXVBHSA-N

物化性质

• 沸点：
  379.7±27.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(methoxymethoxy)phenyl)acrylic acid 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 香豆酸肉桂酯
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441
• 作为产物：
  描述：

  methyl trans-3-(4-methoxymethoxyphenyl)propenoate 在 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以98%的产率得到(E)-3-(4-(methoxymethoxy)phenyl)acrylic acid
  参考文献：
  名称：

  以对甲氧基苄基奎宁酸酯为关键中间体，通过直接酯化反应高效合成5- O-酰基奎宁酸

  摘要：

  从市售（-）-奎宁酸完成了5- O-酰基奎宁酸的有效和通用合成。我们设计了对甲氧基苄基奎宁酸酯作为关键中间体，并解决了两个问题，即空间位阻的5-OH基团的酯化，以实现简洁的发散合成和最终脱保护步骤的收率低。对于第一个问题，我们通过添加i -Pr 2 NEt改进了田边的方法，即使用游离羧酸的TsCl / NMI介导的酯化反应。对于第二个问题，我们为最终的脱保护步骤建立了TFA或BCl 3 / C 6 HMe 5催化的脱保护反应。5 Ø-酰基奎尼酸通过七个步骤合成，总收率为45-60％。

  DOI：

  10.1016/j.tet.2014.08.064

文献信息

• Design, synthesis, and structure activity relationship analysis of new betulinic acid derivatives as potent HIV inhibitors
  作者：Yu Zhao、Chin-Ho Chen、Susan L. Morris-Natschke、Kuo-Hsiung Lee

  DOI：10.1016/j.ejmech.2021.113287

  日期：2021.4

  and evaluated for anti-HIV-1 replication activity against HIV-1NL4-3 infected MT-4 cell lines. Five known and 21 new derivatives were as or more potent than 3 (EC50 0.065 μM), while eight new derivatives were as or more potent than 4 (EC50 0.019 μM). These derivatives feature expanded structural diversity and chemical space that may improve the antiviral activity and address the growing resistance crisis

  桦木酸 ( 1 ) 是一种具有良好抗 HIV 活性的天然产物先导物，其先前的修饰产生了 3 - O -(3',3'-二甲基琥珀酰)桦木酸 (bevirimat, 3 )，这是一流的 HIV 成熟抑制剂。在I 期和 IIa 期临床试验中发现了3种抗性变体后，对3进行进一步修饰产生了4种，其对野生型和3种抗性 HIV-1 的活性有所提高。在优化1的持续努力中，现已设计、合成并评估了 63 种最终产品的抗 HIV-1 复制活性，以对抗 HIV-1 NL4-3感染的 MT-4 细胞系。五种已知衍生物和 21 种新衍生物与3 (EC 50 0.065 μM) 相同或更强效，而八种新衍生物与4 (EC 50 0.019 μM) 相同或更强效。这些衍生物具有扩展的结构多样性和化学空间，可以提高抗病毒活性并解决日益严重的耐药性危机。对构效关系（SAR）相关性进行了深入分析，并构建了具有高可预测性的 3D 定量
• Novel Tranylcypromine/Hydroxylcinnamic Acid Hybrids as Lysine-Specific Demethylase 1 Inhibitors with Potent Antitumor Activity
  作者：Yan Han、Chunlei Wu、Haifeng Lv、Na Liu、Huaying Deng

  DOI：10.1248/cpb.c15-00476

  日期：——

  Novel tranylcypromine/hydroxylcinnamic acid hybrids 15a, b, and 19a-l were designed and synthesized by connecting tranylcypromine with hydroxylcinnamic acid, and their biological activities were evaluated. The in vitro assay of their inhibitory activities against lysine-specific demethylase 1 (LSD1) showed that most of the target compounds displayed high potency with IC50 values ranging from submicromolar

  通过将反式环丙胺与羟基肉桂酸连接，设计并合成了新型的反式环丙胺/羟基肉桂酸杂化物15a，b和19a-1。体外测定其对赖氨酸特异性脱甲基酶1（LSD1）的抑制活性表明，大多数目标化合物显示出高效价，IC50值范围从亚微摩尔到个位数微摩尔水平。特别地，化合物19l具有鲁棒的，选择性的LSD1抑制活性，这明显高于分别对同系物单胺氧化酶-A（MAO-A）和MAO-B的抑制活性。此外，最有效的化合物19l在体外选择性抑制癌细胞，但不抑制非肿瘤结肠细胞的增殖。此外，化合物19l在细胞水平上也剂量依赖性地增加了H3K4me2的表达。我们的发现表明，作为LSD1抑制剂的tranylcypromine / hydroxylcinnamicamic杂种作为治疗人类癌症的治疗剂可能具有广阔的前景。
• ARYL SULFAMATE DERIVATIVES
  申请人：Kyowa Hakko Kogyo Co., Ltd

  公开号：EP1431280A1

  公开（公告）日：2004-06-23

  The present invention provides an aryl sulfamate derivative represented by Formula (I) (wherein Rr and Rs, which may be the same or different, each represent a hydrogen atom or lower alkyl, R1, R2, R3 and R4, which may be the same or different, each represent a hydrogen atom, lower alkyl, a halogen atom, nitro, cyano, azido, or the like, R5 represents a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted lower cycloalkyl, or the like, R6 represents a hydrogen atom, substituted or unsubstituted alkyl, a halogen atom, or the like, or R5 and R6 are joined to form a bond, and R7 represents X1NR23R24 or COR26), or a pharmaceutically acceptable salt thereof.

  本发明提供了一种由式（I）表示的芳基磺酰胺衍生物（其中Rr和Rs可能相同也可能不同，分别表示氢原子或较低的烷基，R1、R2、R3和R4可能相同也可能不同，分别表示氢原子、较低的烷基、卤素原子、硝基、氰基、叠氮基等，R5表示氢原子、取代或未取代的烷基、取代或未取代的较低环烷基等，R6表示氢原子、取代或未取代的烷基、卤素原子等，或R5和R6连接形成键，R7表示X1NR23R24或COR26），或其药学上可接受的盐。
• NOVEL COMPOUND PROMOTING OSTEOBLAST DIFFERENTIATION AND INHIBITING ADIPOCYTE DIFFERENTIATION, PREPARATION METHOD THEREOF AND APPLICATION THEREOF
  申请人：SUNG KYUN BIOTECH CO., LTD.

  公开号：US20190152935A1

  公开（公告）日：2019-05-23

  The present disclosure relates to a compound having the activity of promoting osteoblast differentiation and inhibiting adipocyte differentiation and a preparation method thereof. The novel compound of the present disclosure increases the expression of the gene ALP involved in the differentiation of osteoblasts, regulates expression of the genes PPARγ, aP2 and CD36 involved in the differentiation of adipocytes, increases bone mineral density (BMD) in an ovariectomized osteoporosis animal model and decreases adipocytes in the bone marrow. Therefore, it can be used as an active ingredient of a medication or a health functional food useful for metabolic bone disease or obesity.

  本公开涉及一种具有促进成骨细胞分化和抑制脂肪细胞分化活性的化合物及其制备方法。本公开的新化合物增加了参与成骨细胞分化的ALP基因的表达，调节了参与脂肪细胞分化的PPARγ、aP2和CD36基因的表达，在去势骨质疏松动物模型中增加了骨矿物质密度（BMD）并减少了骨髓中的脂肪细胞。因此，它可以用作药物或健康功能食品的有效成分，用于代谢性骨病或肥胖症。
• Aryl sulfamate derivatives
  申请人：——

  公开号：US20040254241A1

  公开（公告）日：2004-12-16

  The present invention provides an aryl sulfamate derivative represented by Formula (I) 1 (wherein R r and R s , which may be the same or different, each represent a hydrogen atom or lower alkyl R 1 , R 2 , R 3 and R 4 , which may be the same or different, each represent a hydrogen atom, lower alkyl, a halogen atom, nitro, cyano, azido, or the like, R 5 represents a hydrogen atom, substituted or unsubstituted alkyl, substituted or unsubstituted lower cycloalkyl, or the like, R 6 represents a hydrogen atom, substituted or unsubstituted alkyl, a halogen atom, or the like, or R 5 and R 6 are joined to form a bond, and R 7 represents X 1 NR 23 R 24 or COR 26 ), or a pharmaceutically acceptable salt thereof.

  本发明提供一种由式（I）1表示的芳基磺酰胺衍生物（其中Rr和Rs，可以相同也可以不同，均表示氢原子或低级烷基，R1、R2、R3和R4，可以相同也可以不同，均表示氢原子、低级烷基、卤素原子、硝基、氰基、叠氮基等，R5表示氢原子、取代或未取代的烷基、取代或未取代的低环烷基等，R6表示氢原子、取代或未取代的烷基、卤素原子等，或R5和R6结合形成键，R7表示X1NR23R24或COR26，或其药学上可接受的盐）。