(E)-3-(4-hydroxy-3-methoxyphenyl)-N-adamantyl-propeneamide

• 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-hydroxy-3-methoxyphenyl)-N-adamantyl-propeneamide
• 英文别名: (E)-N-(1-adamantyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: DALFYKTUUOPSDN-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以45.9%的产率得到(E)-3-(4-hydroxy-3-methoxyphenyl)-N-adamantyl-propeneamide
  参考文献：
  名称：

  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives

  摘要：

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.024

文献信息

• Synthesis and biological activity of hydroxycinnamoyl containing antiviral drugs
  作者：Maya Chochkova、Assya Georgieva、Galya Ivanova、Nadya Nikolova、Luchia Mukova、Lubomira Nikolaeva-Glomb、Tsenka Milkova

  DOI：10.2298/jsc130222103c

  日期：——

  Seven N-hydroxycinnamoyl amides were synthesized by EDC/HOBt coupling of the corresponding substituted cinnamic acids (p-coumaric-, ferulic-, sinapic- and caffeic acids) with influenza antivirals (amantadine, rimantadine and oseltamivir). DPPH (1,1-diphenyl-2-picrylhydrazyl) scavenging abilities and the inhibitory effect on mushroom tyrosinase activity (using L-tyrosine as the substrate) were investigated in vitro. Amongst the synthesized compounds, N-[(E)-3-(3?,4?-dihydroxyphenyl)-2-propenoyl]oseltamivir (1) and N-[(E)-3-(3?,4?-dihydroxyphenyl)-2-propenoyl]rimantadine (4), containing catechol moiety, exhibited the most potent DPPH radical-scavenging activity. Amide (1) displayed also tyrosinase inhibitory effect toward L-tyrosine as the substrate (~50%). Due to its biological activities revealed so far compound (1) can be considered as a promising candidate for a cosmetic ingredient. The synthesized compounds were also investigated for their in vitro inhibitory activity against the replication of influenza virus A (H3N2).

  通过 EDC/HOBt 偶联相应的取代肉桂酸（对香豆素、阿魏酸、山奈酸），合成了七种 N-羟基肉桂酰酰胺。 通过 EDC/HOBt 偶联相应的取代肉桂酸（对香豆酸、阿魏酸、山奈酸和咖啡酸 和咖啡酸）与流感抗病毒药物（金刚烷胺、利曼他定和奥司他韦）通过 EDC/HOBt 偶联合成。 奥司他韦）。DPPH（1,1-二苯基-2-苦基肼）清除能力和对蘑菇的抑制作用。 对蘑菇酪氨酸酶活性的抑制作用（以 L-酪氨酸为底物 底物）的抑制作用。在合成的 在合成的化合物中，N-[(E)-3-(3?,4?-二羟基苯基)-2-丙烯酰]奥司他韦 (1) 和 N-[(E)-3-(3?,4?-二羟基苯基)-2-丙烯酰基]利曼他定 (4)。 含有儿茶酚分子的 N-[(E)-3-(3?,4?-二羟基苯基-2-丙烯酰基]利曼他定（4）表现出最强的 DPPH 自由基清除活性。 酰胺 (1) 对以 L-酪氨酸为底物的酪氨酸酶也有抑制作用（约为 50%）。 抑制作用（~50%）。由于迄今为止所揭示的生物活性 化合物 (1) 被认为是一种很有前途的化妆品候选成分。 成分。还研究了合成的化合物对酪氨酸的体外抑制活性。 体外抑制甲型流感病毒（H3N2）复制的活性。 (H3N2) 的体外抑制活性。
• [EN] HYDROXYCINNAMIC ACID DERIVATIVES AND PREPARATION METHOD THEREOF AND COSMETIC COMPOSITION CONTAINING IT<br/>[FR] DÉRIVÉS D'ACIDE HYDROXYCINNAMIQUE ET LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITION COSMÉTIQUE LES CONTENANT
  申请人：AMOREPACIFIC CORP

  公开号：WO2008018683A1

  公开（公告）日：2008-02-14

  [EN] The present invention relates to hydroxycinnamic acid derivatives conjugated with adamantylamide, a preparation method thereof and cosmetic compositions containing the same. The hydroxycinnamic acid derivatives of the present invention have activities of inhibiting melanin generation by anti-oxidation and promoting collagen synthesis. Therefore, compositions containing the derivatives of the invention can be effectively used as cosmetic compositions with anti-oxidation effect, skin pigmentation improving effect and anti-wrinkle effect by promoting collagen synthesis.
  [FR] La présente invention concerne des dérivés d'acide hydroxycinnamique conjugués avec de l'adamantylamide, leur procédé de préparation et des compositions cosmétiques les contenant. Les dérivés d'acide hydroxycinnamique de la présente invention présentent des activités d'inhibition de la génération de mélanine par anti-oxydation et de renforcement de la synthèse de collagène. C'est pourquoi les compositions contenant les dérivés de l'invention peuvent être efficacement utilisées en tant que compositions cosmétiques à effet anti-oxydant, effet améliorant sur la pigmentation cutanée et effet anti-rides par renforcement de la synthèse de collagène.
• Synthesis and antitumor activity of feruloyl and caffeoyl derivatives
  作者：Hui-zhen Chen、You-bao Chen、Ya-ping Lv、Fang Zeng、Juan Zhang、Yong-lie Zhou、Han-bing Li、Li-fei Chen、Bin-jie Zhou、Jian-rong Gao、Chun-nian Xia

  DOI：10.1016/j.bmcl.2014.08.024

  日期：2014.9

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.