N-trans-caffeoyltryptamine | 945453-47-4

• 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-trans-caffeoyltryptamine
• 英文别名: trans-N-caffeoyltryptamine；N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dihydroxyphenyl)acrylamide；Safflomide；N-caffeoyltryptamine；(E)-N-[2-(3-Indolyl)ethyl]-3-(3,4-dihydroxyphenyl)acrylamide；(E)-3-(3,4-dihydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
• CAS: 945453-47-4
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: LNKPAQNDSCOUPS-SOFGYWHQSA-N

物化性质

• 熔点：
  186-187 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  687.7±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.4
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-4-(3-((2-(1H-indol-3-yl)ethyl)amino)-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate 在 一水合肼 作用下， 生成 N-trans-caffeoyltryptamine
  参考文献：
  名称：

  N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells

  摘要：

  A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from mouse B16 and human HMV-II melanoma cells, while the corresponding derivatives of tryptamine and 5-methoxytryptamine were almost inactive or less active than the serotonin derivatives. The inhibitory activity of the serotonin derivatives increased with increasing number of phenolic hydroxyl groups in the acyl moiety. Melanin formation in the culture of B16 cells was suppressed by 3 and 9 with no cytotoxicity in the concentration range tested (IC50 = 15, 3 and 111 mu M for 3, 9, and kojic acid, respectively). Thus the N-acylserotonin derivatives having a dihydroxyphenyl group are potential anti-melanogenic agents. Their inhibition of tyrosinase is primarily performed through the 5-hydroxyindole moiety and further strengthened by the phenolic hydroxyl groups in the acyl moiety. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.115

文献信息

• Design and synthesis of novel caffeic acid phenethyl ester (CAPE) derivatives and their biological activity studies in glioblastoma multiforme (GBM) cancer cell lines
  作者：Bilgesu Onur Sucu、Elif Beyza Koc、Ozgecan Savlug Ipek、Afranur Mirat、Furkan Almas、Melike Aybala Guzel、Berna Dogan、Damla Uludag、Nihal Karakas、Serdar Durdagi、Mustafa Guzel

  DOI：10.1016/j.jmgm.2022.108160

  日期：2022.6

  inability of the drugs used to cross the blood-brain barrier (BBB). Thus, developing more effective and potent medicines for GBM are needed. There have been several reports demonstrating that CAPE presents reasonably good anti-cancer activity in certain cancer cell lines and can penetrate the blood-brain barrier. Accordingly, in this study we synthesized several novel CAPE analogs with the addition of more

  多形性胶质母细胞瘤 (GBM) 是最具侵袭性的脑肿瘤，被列为最致命的癌症之一。目前针对 GBM 的治疗计划仍然无效，因为其进展迅速且用于穿过血脑屏障 (BBB) 的药物无法通过。因此，需要开发更有效、更有效的 GBM 药物。有几份报告表明，CAPE 在某些癌细胞系中表现出相当好的抗癌活性，并且可以穿透血脑屏障。因此，在这项研究中，我们合成了几种新的 CAPE 类似物，并添加了更多的可成药手柄和增溶实体，随后在体外评估了它们GBM 细胞系 (T98G 和 LN229) 的治疗效果。然后对最有效的化合物进行了广泛检查，结果表明，与 CAPE 本身相比， 50 μM 新型 CAPE 类似物（化合物10 ）显着降低了 T98G 和 LN229 GBM 细胞的活力。此外，相同浓度的化合物10对健康人细胞（成纤维细胞样间充质干细胞）没有细胞毒性。在化合物10处理组中分别检测到 LN229 和 T98G的凋亡（32
• Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry
  作者：Siyu Wang、Joon Hyuk Suh、Xi Zheng、Yu Wang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.6b05136

  日期：2017.1.18

  their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized

  枸杞子或枸杞的果枸杞，具有促进健康的特性，导致其有效成分的深入研究。我们合成了一组羟基肉桂酸酰胺（HCCA）化合物，包括反式咖啡酸，反式-阿魏酸和3,4-二羟基氢肉桂酸（含扩展的酚胺成分）作为标准品，用于鉴定和定量枸杞中的相应化合物，并使用体外模型研究这些化合物的抗炎特性。通过优化的LC-MS / MS和NMR分析，从水果中鉴定出9种酰胺化合物。这些化合物中有7种是首次在该植物中鉴定出来的。具有酪胺部分的酰胺化合物最丰富。体外研究表明，5个HCCA化合物显示出对NO产生由脂多糖与IC inuded抑制作用50小于15.08μM（反式- ñ -feruloyl多巴胺）。这些发现表明，枸杞具有抗炎特性。
• Synthesis, biological evaluation, and structure–activity relationship study of novel cytotoxic aza-caffeic acid derivatives
  作者：Hongbin Zou、Hao Wu、Xiangnan Zhang、Yu Zhao、Joachim Stöckigt、Yijia Lou、Yongping Yu

  DOI：10.1016/j.bmc.2010.07.016

  日期：2010.9

  Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl) prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC(50) values of 0.2, 2.0, 1.7, and 1.1 mu M, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner. (C) 2010 Elsevier Ltd. All rights reserved.
• Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides
  作者：Lyubomir Georgiev、Maya Chochkova、Iskra Totseva、Katya Seizova、Emma Marinova、Galya Ivanova、Mariana Ninova、Hristo Najdenski、Tsenka Milkova

  DOI：10.1007/s00044-012-0419-x

  日期：2013.9

  Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.
• JP2009263282A
  申请人：——

  公开号：JP2009263282A

  公开（公告）日：2009-11-12