(E)-3-(4-氯苯基)-N-(2-羟基乙基)丙-2-烯酰胺 | 30687-04-8

• 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: (E)-3-(4-氯苯基)-N-(2-羟基乙基)丙-2-烯酰胺
• 英文名称: (E)-3-(4-chlorophenyl)-N-(2-hydroxyethyl)acrylamide
• 英文别名: 4-Chloro-N-(2-hydroxyethyl)cinnamamide；(E)-3-(4-chlorophenyl)-N-(2-hydroxyethyl)prop-2-enamide
• CAS: 30687-04-8
• 化学式: C₁₁H₁₂ClNO₂
• mdl: MFCD01736674
• 分子量: 225.675
• InChiKey: RHBQLRHLQXLTSV-ZZXKWVIFSA-N

物化性质

• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-氯苯基)-N-(2-羟基乙基)丙-2-烯酰胺 、 双氢青蒿素 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到
  参考文献：
  名称：

  Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104903
• 作为产物：
  描述：

  对氯肉桂酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-3-(4-氯苯基)-N-(2-羟基乙基)丙-2-烯酰胺
  参考文献：
  名称：

  Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice

  摘要：

  This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, (1)H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.

  DOI：

  10.1007/s00044-010-9470-7

文献信息

• 10.1016/j.bioorg.2024.107533
  作者：Gunia-Krzyżak, Agnieszka、Popiół, Justyna、Słoczyńska, Karolina、Żelaszczyk, Dorota、Koczurkiewicz-Adamczyk, Paulina、Wójcik-Pszczoła, Katarzyna、Bucki, Adam、Sapa, Michał、Kasza, Patryk、Borczuch-Kostańska, Magda、Marona, Henryk、Pękala, Elżbieta

  DOI：10.1016/j.bioorg.2024.107533

  日期：——

  safe melanogenesis inhibitors for possible use in topical cosmetic depigmenting formulations. Cinnamic acid derivatives constitute a widely tested group for that purpose. This article reports research in the group of -alkyl cinnamamide derivatives (un)substituted in phenyl ring. Among tested series, ()-3-(4-chlorophenyl)--(5-hydroxypentyl)acrylamide (compound ) showed the most promising inhibitory properties

  色素沉着过度疾病可能是由不适当的黑色素沉积和/或过度的黑色素合成引起的。它们主要被归类为审美问题，但它们会降低自尊，从而严重影响人类健康。对于色素沉着过度病症，仅有有限的治疗选择，其中包括局部使用的化妆品。人们发现脱色成分无效并且具有各种副作用。因此，人们做出了许多努力来发现新颖、有效且安全的黑素生成抑制剂，以用于局部化妆品脱色配方。肉桂酸衍生物构成了用于此目的的经过广泛测试的组。本文报道了苯环上（未）取代的-烷基肉桂酰胺衍生物组的研究。在测试的系列中，()-3-(4-氯苯基)--(5-羟基戊基)丙烯酰胺（化合物 ）在蘑菇酪氨酸酶测定中显示出最有前途的抑制特性（对于单酚酶活性，IC = 36.98 ± 1.07 µM，IC = 146.71 ±双酚酶活性为 16.82 µM），浓度 6.25 µM 时 B16F10 小鼠黑色素瘤细胞系中黑色素生成受到抑制，可能是由于 、 和 基因表达减少所致。当在
• US4512994A
  申请人：——

  公开号：US4512994A

  公开（公告）日：1985-04-23
• Discovery of novel dihydroartemisinin-cinnamic hybrids inducing lung cancer cells apoptosis via inhibition of Akt/Bad signal pathway
  作者：Yanping Hu、Yujin Wang、Na Li、Li Chen、Jianbo Sun

  DOI：10.1016/j.bioorg.2021.104903

  日期：2021.6
• Synthesis and antidepressant-like action of N-(2-hydroxyethyl) cinnamamide derivatives in mice
  作者：Xian-Qing Deng、Di Wu、Cheng-Xi Wei、Zhe-Shan Quan

  DOI：10.1007/s00044-010-9470-7

  日期：2011.11

  This study described the chemical synthesis and pharmacological evaluation of a series of N-(2-hydroxyethyl) cinnamamide derivatives. The structures of them were characterized by IR, (1)H-NMR, MS and elemental analysis. Their antidepressant activities were evaluated by the forced swimming test (FST) and tail suspension test (TST). Pharmacological results of these compounds showed that some of them, given orally, significantly reduced the immobility time in the FST and TST, indicating the antidepressant-like action. Among them, compounds N-(2-hydroxyethyl)cinnamamide (1g), (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-hydroxyethyl)acrylamide (1i) and (E)-N-(2-hydroxyethyl)-3-(3-hydroxyphenyl)acrylamide (1n), active in the two models, were considered as the most promising compounds in this study.