3-(2-甲氧基萘-1-基)丙-2-烯酸 | 106276-48-6

• 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
• 中文名称: 3-(2-甲氧基萘-1-基)丙-2-烯酸
• 英文名称: 3-(2-methoxynaphthalen-1-yl)acrylic acid
• 英文别名: 2-Propenoic acid, 3-(2-methoxy-1-naphthalenyl)-；3-(2-methoxynaphthalen-1-yl)prop-2-enoic acid
• CAS: 106276-48-6
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: AOYGYGJJEGVZLW-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  426.8±20.0 °C(Predicted)
• 密度：
  1.246±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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-甲氧基萘-1-基)丙-2-烯酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到3-(2-甲氧基-1-萘基)丙酸
  参考文献：
  名称：

  Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents

  摘要：

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.032
• 作为产物：
  描述：

  2-甲氧基-1-萘醛 在 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 3-(2-甲氧基萘-1-基)丙-2-烯酸
  参考文献：
  名称：

  Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid

  摘要：

  The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.080

文献信息

• Design, synthesis and evaluation of amino-substituted 1H-phenalen-1-ones as anti-leishmanial agents
  作者：Mónica Blanco Freijo、Atteneri López-Arencibia、José E. Piñero、Grant McNaughton-Smith、Teresa Abad-Grillo

  DOI：10.1016/j.ejmech.2017.10.032

  日期：2018.1

  Screening of a designed collection of mono-substituted amino-IH-phenalen-1-ones against promastigote forms of L. donovani and L. amazonensis, identified seven compounds with anti-leishmanial activities comparable or better than the commonly prescribed anti-leishmanial drug, miltefosine. Structure activity analysis revealed that appendages containing a basic tertiary nitrogen were favored, and that the position of the appendage also affected their potency. Like miltefosine, several of these active compounds significantly reduced the mitochondrial membrane potential in promastigotes. Further studies in amastigotes of L. amazonensis revealed that compounds 14, 15 and 33 were more active and more selective than miltefosine, with sub-micromolar potencies and selectivity indices > 100. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid
  作者：Seisuke Mimori、Yukari Koshikawa、Yu Mashima、Katsuyoshi Mitsunaga、Koichi Kawada、Masayuki Kaneko、Yasunobu Okuma、Yasuyuki Nomura、Yasuoki Murakami、Tetsuto Kanzaki、Hiroshi Hamana

  DOI：10.1016/j.bmcl.2014.12.080

  日期：2015.2

  The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene. (C) 2015 Elsevier Ltd. All rights reserved.