(E)-3-(4-羟基苯基)-N-(4-((E)-3-(4-羟基苯基)丙烯酰氨基)丁基)-N-(3-((E)-3-(4-羟基苯基)丙烯酰氨基)丙基)丙烯酰胺 | 131086-78-7

• 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-羟基苯基)-N-(4-((E)-3-(4-羟基苯基)丙烯酰氨基)丁基)-N-(3-((E)-3-(4-羟基苯基)丙烯酰氨基)丙基)丙烯酰胺
• 英文名称: tricoumaroyl spermidine
• 英文别名: N¹,N⁵,N¹⁰-tri-p-coumaroylspermidine；tri-p-coumaroylspermidine；N¹-,N⁵-,N¹⁰-tri-p-(E)-coumaroylspermidine；N¹,N⁵,N¹⁰-(E)-tri-p-coumaroylspermidine；(E)-3-(4-hydroxyphenyl)-N-[4-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-[3-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]propyl]amino]butyl]prop-2-enamide
• CAS: 131086-78-7
• 化学式: C₃₄H₃₇N₃O₆
• 分子量: 583.684
• InChiKey: PFDVWJCSCYDRMZ-AUCPOXKISA-N

物化性质

• 熔点：
  176-180 °C
• 沸点：
  954.2±65.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 储存条件：
  2-8℃

制备方法与用途

(E)-tri-P-coumaroylspermidine是一种亚精胺化合物，存在于胡萝卜素属植物小花中。

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-羟基苯基)-N-(4-((E)-3-(4-羟基苯基)丙烯酰氨基)丁基)-N-(3-((E)-3-(4-羟基苯基)丙烯酰氨基)丙基)丙烯酰胺 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 4.0h， 生成 4-香豆酸
  参考文献：
  名称：

  Trisubstituted hydroxycinnamic acid spermidines from Quercus dentata pollen

  摘要：

  Three novel and one known hydroxycinnamic acid amides were isolated from pollen of Quercus dentata Thunb. They were identified as N-1,N-5,N-10-tricaffeoylspermidine, N-1-p-coumaroyl-N-5,N-10-dicaffeoylspermidine, N-1,N-10-di-p-coumaroyl-N-5-caffeoylspermidine and N-1,N-5,N-10-tri-p-coumaroylspermidine, respectively. Information on the position of the hydroxycinnamoyl moieties was derived from electrospray mass spectral fragmentation patterns.

  DOI：

  10.1016/0031-9422(95)00151-v
• 作为产物：
  描述：

  亚精胺 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (E)-3-(4-羟基苯基)-N-(4-((E)-3-(4-羟基苯基)丙烯酰氨基)丁基)-N-(3-((E)-3-(4-羟基苯基)丙烯酰氨基)丙基)丙烯酰胺
  参考文献：
  名称：

  A New Nonpeptide Tachykinin NK1 Receptor Antagonist Isolated from the Plants of Compositae.

  摘要：

  为了从天然来源中发现新的速激肽NK1受体拮抗剂，我们利用离体豚鼠回肠检测了大约200种植物提取物的速激肽拮抗活性。结果，我们在母菊（Matricaria chamomilla L.）干花的提取物中发现了一种新型且强效的NK1受体拮抗剂。该拮抗剂的结构被确定为N1，N5，N10，N14-四[3-(4-羟基苯基)-2-丙烯酰基]-1，5，10，14-四氮杂十四烷（四香豆酰精胺，1a）。根据其对物质P（SP）诱导的豚鼠回肠收缩的抑制作用以及对[3H][Sar9，Met(O2)11]SP与人NK1受体结合的抑制作用，估算出1a的Ki值分别为21.9 nM和3.3 nM。1a是从天然来源中发现的首例强效NK1受体拮抗剂，它具有独特的多酰化精胺结构。1a主要集中在母菊的花粉中，并且在其他四种菊科植物的花提取物中也有发现。此外，我们在母菊花的提取物中发现了一种新化合物N1，N5，N10-三[3-(4-羟基苯基)-2-丙烯酰基]-1，5，10，14-四氮杂十四烷（2），该化合物不显示任何速激肽拮抗活性。我们还合成了许多相关化合物，并研究了结构-活性关系。

  DOI：

  10.1248/cpb.50.47

文献信息

• Inhibitory Effects on HIV-1 Protease of Tri-p-coumaroylspermidine from Artemisia caruifolia and Related Amides.
  作者：Chao-Mei MA、Norio NAKAMURA、Masao HATTORI

  DOI：10.1248/cpb.49.915

  日期：——

  From a methanol extract of Artemisia caruifolia, which showed a moderate inhibitory activity on HIV-1 protease in a preliminary screening, N1, N5, N10-tri-p-coumaroylspermidine and three dicaffeoylquinic acids were isolated. The former compound was found to appreciably inhibit HIV-1 protease. Of related amides which were chemically synthesized, N1, N5, N10, N14-tetra-p-coumaroylspermine and N1, N4, N7, N10, N13-penta-p-coumaroyltetraethylenepentamine inhibited HIV-1 protease more potently than N1, N5, N10-tri-p-coumaroylspermidine.

  在初步筛选中，青蒿的甲醇提取物对 HIV-1 蛋白酶显示出中等程度的抑制活性，从这种提取物中分离出了 N1、N5、N10-三对香豆酰丝氨酸和三种二咖啡酰奎宁酸。发现前一种化合物对 HIV-1 蛋白酶有明显的抑制作用。在化学合成的相关酰胺中，N1、N5、N10、N14-四对香豆酰过胺和 N1、N4、N7、N10、N13-五对香豆酰四乙烯五胺对 HIV-1 蛋白酶的抑制作用强于 N1、N5、N10-三对香豆酰过胺。
• Antifungal Polyamides of Hydroxycinnamic Acids from Sunflower Bee Pollen
  作者：Jan Kyselka、Roman Bleha、Miroslav Dragoun、Kristýna Bialasová、Šárka Horáčková、Martin Schätz、Marcela Sluková、Vladimír Filip、Andriy Synytsya

  DOI：10.1021/acs.jafc.8b03976

  日期：2018.10.24

  bioassay-guided fractionation was the selection of the most potent group of compounds responsible for the protection of sunflower bee pollen grains. Synthesis of prospective antifungal polyamides of hydroxycinnamic acids was based on previous structural elucidation of ethanol soluble fraction by 1H,1H-PFG-COSY, 1H,13C-HSQC, FT-IR, FT-Raman, and LC–MS experiments. The main compounds found were tri-p-coumaroylspermidines

  生物测定指导分级分离的目的是选择最有效的一组化合物来保护向日葵蜂花粉粒。羟基肉桂酸的预期抗真菌聚酰胺的合成是基于先前对乙醇可溶级分的结构解析，方法是1 H，1 H-PFG-COSY，1 H，13 C-HSQC，FT-IR，FT-Raman和LC-MS实验。发现的主要化合物为三对-香豆酰亚精胺，并伴有其他亚精胺和腐胺的HCAA。制备了几种HCAA模型衍生物以测试其对广泛变质真菌的抗真菌活性（A.niger 42 CCM 8189，F。culmorum DMF 0103和P.verrucosum DMF 0023）。A.niger CCM 8189和F. culmorum DMF 0103对羟肉桂酰胺的抗真菌作用表现出更高的抗性，而疣状假单胞菌DMF 0023是最敏感的菌株。已经发现HCAA极性对次级代谢产物在花粉粒的微生物保护中的作用。生物测定指导的分级分离，结构阐明，预期化合物的选择以及它
• Synthese derp-Cumaroylspermidine
  作者：Wenqing Hu、Manfred Hesse

  DOI：10.1002/hlca.19960790222

  日期：1996.3.20

  The Synthesis of p‐CumaroylspermidinesThe synthesis of three mono[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines, 10, 20, and 28, three bis[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines, 6, 16, and 25, and one tris[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]‐spermidine is described.
• Synthesis of 13C-dilabeled 4-coumaroylspermidines
  作者：Hervé Geneste、Manfred Hesse

  DOI：10.1016/s0040-4020(98)01014-x

  日期：1998.12

  Five C-13-dilabeled constitution isomers of 4-coumaroylspermidines were prepared in nine to eleven steps: N-1,4-di[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (13b), N-1-[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (17b), N-1,8-di[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (20b), N-4-[(E)-4-coumaroyl]-(1,4-C-13(2))spermidine (24b) and N-1,4,8-tri[(E)-4-coumaroyl]-(5,8-C-13(2))spermidine (26). The two C-13-atoms were subsequently introduced using labeled potassium cyanide. The synthesis proceeds through stepwise construction of the polyamine backbone including protection and deprotection steps of the amino functions. Based on H-1-H-1 NOE interactions, the preliminary study of their binding reveals that 20b binds to tRNA in the. same way as spermidine does, whereas 24b and 26 do not-show any NOE effects with the tRNA protons. (C) 1998 Elsevier Science Ltd. All rights reserved.
• The unusual conformational preference of N1,N5,N10-tri-p-coumaroylspermidine E-Z isomers from the Japanese apricot tree, Prunus mume, for the (ZZZ)-form
  作者：Shinnosuke Mori、Miki Akamatsu、Hiroshi Fukui、Junko Tsukioka、Katsumi Goto、Nobuhiro Hirai

  DOI：10.1016/j.phytol.2019.02.028

  日期：2019.6

  The Japanese apricot tree, Prunus mume (Siebold) Siebold & Zucc. cv. Nanko, bears two types of flowers: those with anthers that fluoresce under UV irradiation, and those that do not. The chemical composition of both types of anthers has been investigated: the non-fluorescent anthers contained eight E-Z isomers of N-1,N-5,N-1(0)-tri-p-coumaroylspermidine as major constituents; whereas the fluorescent anthers contained only a limited amount of (ZZZ)-isomer, but relatively large amounts of fluorescent chlorogenic acid, implying the abnormal development of fluorescent anthers. Of these eight E-Z isomers, three were undescribed, and identified as the (ZEZ)-, (ZEE)-, and (EEZ)-forms. Their photoequilibrium ratios were found to be characteristic, wherein the (ZZZ)-isomer predominated over the (EEE). H-1 NMR and NOESY experiments and ab initio molecular orbital calculations indicated that intramolecular T-shaped pi/pi, CH/pi, and OH center dot center dot center dot O = C hydrogen bonding interactions impart an unusual degree of stability to the (ZZZ)-isomer that is sufficient to overcome various factors that favor the (EEE)-form.