N-(4-hydroxyphenethyl)cinnamamide

• 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: N-(4-hydroxyphenethyl)cinnamamide
• 英文别名: N-trans-cinnamoyltyramine；N-(cinnamoyl)tyramine；N-cinnamoyltyramine；cinnamoyltyramine；N-[2-(4-Hydroxyphenyl)ethyl]-3-phenylprop-2-enamide
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: KGOYCHSKGXJDND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-hydroxyphenethyl)cinnamamide 在 碘苯二乙酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 2.0h， 以23%的产率得到melodamide A
  参考文献：
  名称：

  Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum

  摘要：

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.

  DOI：

  10.1055/s-0032-1328131
• 作为产物：
  描述：

  对羟基苯乙胺 、 肉桂酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三甲胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N-(4-hydroxyphenethyl)cinnamamide
  参考文献：
  名称：

  Tri藜的肉桂酸酰胺表现出无竞争性的α-葡萄糖苷酶抑制作用

  摘要：

  reported藜提取物具有抑制α-葡萄糖苷酶的潜力，但至今尚无有效成分的信息。这项研究试图分离负责的代谢产物，并阐明其对α-葡萄糖苷酶的抑制机制。通过分馏T. terristris提取物，三肉桂酸酰胺衍生物（1 - 3）中确定具有对抗α葡糖苷酶的活性组分。引线结构，ñ -反式-coumaroyltyramine 1，表明α葡萄糖苷酶的抑制显著（IC 50 = 0.42μM）。此外，所有活性化合物均显示出非竞争性的抑制机制，很少有关于α-葡萄糖苷酶抑制剂的报道。通过显示K m和V max以及K ik / K iv之比在1.029至1.053之间的降低，充分证明了该动力学行为。我们进行了研究，以研究如何对铅结构进行化学修饰1可能会影响抑制。肉桂酸酰胺的A环中的α，β-不饱和羰基和羟基已成为抑制α-葡糖苷酶的关键功能。分子模型研究表明，抑制活性与酶和抑制剂之间的π-π相互作用以及氢键相互作用密切相关。

  DOI：

  10.1016/j.ejmech.2016.02.044

文献信息

• 一锅合成花椒素WGX-50及其衍生物的方法
  申请人：上海彤颜实业有限公司

  公开号：CN114315623A

  公开（公告）日：2022-04-12

  本发明公开了一锅合成花椒素WGX‑50及其衍生物的方法，该方法通过将芳香醛、乙酸酐、芳香胺在一个稳定的催化体系中，控制不同物质的添加时间和添加方式，一锅合成高收率、高纯度的花椒素WGX‑50及其衍生物。
• Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals
  作者：Yang Yang、Zhi-Guang Song、Zai-Qun Liu

  DOI：10.3109/10715762.2010.540576

  日期：2011.4

  Cinnamoylphenethylamine (CNPA) derivatives including feruloylphenethylamine (FRPA), caffeoylphenethylamine (CFPA), cinnamoyltyramine (CNTA), feruloyltyramine (FRTA) and caffeoyltyramine (CFTA) were synthesized in order to investigate the influence of the number and position of hydroxyl group on Cu2+/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. The radical-scavenging properties of these CNPA derivatives were also evaluated by trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) and galvinoxyl radical. In addition, these CNPA derivatives were tested by linoleic acid (LH)-beta-carotene-bleaching experiment. The chemical kinetic was employed to treat the results from AAPH-induced oxidation of DNA and gave the order of antioxidant ability as CFTA > CFPA > FRTA > FRPA. CFTA and CFPA also possessed high abilities to inhibit Cu2+/GSH-mediated degradation of DNA, whereas FRPA and FRTA can protect LH against the auto-oxidation efficiently. Finally, CFPA and FRPA exhibited high activity in trapping ABTS(+center dot), DPPH and galvinoxyl radicals. Therefore, the cinnamoyl group bearing ortho-dihydroxyl or hydroxyl with ortho-methoxyl benefited for CNPA derivatives to protect DNA, while hydroxyl in tyramine cannot enhance the radical-scavenging abilities of CNPA derivatives.
• Structure−Activity Relationships and Cancer-Cell Selective Toxicity of Novel Inhibitors of Glioma-Associated Oncogene Homologue 1 (Gli1) Mediated Transcription
  作者：Neeraj Mahindroo、Michele C. Connelly、Chandanamali Punchihewa、Hiromichi Kimura、Matthew P. Smeltzer、Song Wu、Naoaki Fujii

  DOI：10.1021/jm900106f

  日期：2009.7.23

  We report novel inhibitors of Gli1-mediated transcription as potential anticancer agents. Focused chemical libraries were designed and assessed for inhibition of functional cell-based Gli1-mediated transcription and selective toxicity toward cancer cells. The SAR was revealed, and the selectivity of the lead compounds' inhibition of Gli1-mediated transcription over that of Gli2 was determined. Compound 63 (NMDA298-1), which inhibited Gli1-mediated transcription in C3H10T1/2 cells with all IC50 of 6.9 mu M, showed 3-fold selectivity for inhibiting transcription mediated by Gli1 over that by Gli2. Cell-viability assays were performed to evaluate the chemical library in a normal cell line and a panel of cancer cell lines with or without up-regulated expression of the Gli1 gene. These compounds decreased the viability of several cancer cell lines but were less active in the noncancerous BJ-hTERT cells.
• Cinnamic acid amides from Tribulus terrestris displaying uncompetitive α-glucosidase inhibition
  作者：Yeong Hun Song、Dae Wook Kim、Marcus J. Curtis-Long、Chanin Park、Minky Son、Jeong Yoon Kim、Heung Joo Yuk、Keun Woo Lee、Ki Hun Park

  DOI：10.1016/j.ejmech.2016.02.044

  日期：2016.5

  active ingredients are unknown. This study attempted to isolate the responsible metabolites and elucidate their inhibition mechanism of α-glucosidase. By fractionating T. terristris extracts, three cinnamic acid amide derivatives (1–3) were ascertained to be active components against α-glucosidase. The lead structure, N-trans-coumaroyltyramine 1, showed significant inhibition of α-glucosidase (IC50 = 0

  reported藜提取物具有抑制α-葡萄糖苷酶的潜力，但至今尚无有效成分的信息。这项研究试图分离负责的代谢产物，并阐明其对α-葡萄糖苷酶的抑制机制。通过分馏T. terristris提取物，三肉桂酸酰胺衍生物（1 - 3）中确定具有对抗α葡糖苷酶的活性组分。引线结构，ñ -反式-coumaroyltyramine 1，表明α葡萄糖苷酶的抑制显著（IC 50 = 0.42μM）。此外，所有活性化合物均显示出非竞争性的抑制机制，很少有关于α-葡萄糖苷酶抑制剂的报道。通过显示K m和V max以及K ik / K iv之比在1.029至1.053之间的降低，充分证明了该动力学行为。我们进行了研究，以研究如何对铅结构进行化学修饰1可能会影响抑制。肉桂酸酰胺的A环中的α，β-不饱和羰基和羟基已成为抑制α-葡糖苷酶的关键功能。分子模型研究表明，抑制活性与酶和抑制剂之间的π-π相互作用以及氢键相互作用密切相关。
• Isolation and Synthesis of Melodamide A, a New Anti-inflammatory Phenolic Amide from the Leaves of Melodorum fruticosum
  作者：Hsiu-Hui Chan、Tsong-Long Hwang、Tran Thang、Yann-Lii Leu、Ping-Chung Kuo、Bui Nguyet、Do Dai、Tian-Shung Wu

  DOI：10.1055/s-0032-1328131

  日期：——

  Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 mu M. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.