N-trans-sinapoyltyramine

• 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-sinapoyltyramine
• 英文别名: (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: IEDBNTAKVGBZEP-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对羟基苯乙胺 、 3,5-二甲氧基-4-羟基肉桂酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以50%的产率得到N-trans-sinapoyltyramine
  参考文献：
  名称：

  用于控制浸润性乳腺癌的新型c-Met抑制性橄榄类拟南芥半合成类似物。

  摘要：

  受体酪氨酸激酶c-Met失调及其配体HGF是治疗癌症的有效且有吸引力的分子靶标。受天然存在的橄榄类secrididoid（-）-oleocanthal（1）的化学结构的启发，并记录了其对c-Met依赖性恶性肿瘤的抗癌活性，以前的一项研究报道了酪氨酸溶胶鼻血酸盐（4）作为c-Met抑制剂的命中物。这项研究报告了额外的半合成优化和4的SAR，以通过增加其抑制c-Met磷酸化的能力来提高其对c-Met依赖性乳腺癌的选择性活性。合成了四十三种化合物（5-47），其中新颖的类似物高香草酸芥子酸酯（HVS-16）以其卓越的活性而著称。HVS-16大大削弱了c-Met介导的增殖，迁移，和在二维和三维培养系统中跨越人乳腺癌细胞系的侵袭，而发现相似的治疗剂量既不影响非致瘤性人乳腺上皮细胞的生长，也不影响c-Met独立乳腺癌细胞的生存能力。HVS-16在人乳腺癌细胞中显示出剂量依赖性抑制配体介导的c-Met活

  DOI：

  10.1016/j.ejmech.2016.04.043

文献信息

• [EN] METHODS FOR TREATING C-MET-DEPENDENT CANCERS<br/>[FR] PROCÉDÉS DE TRAITEMENT DES CANCERS DÉPENDANT DE C-MET
  申请人：CARDELLI JAMES ALLEN

  公开号：WO2017123935A1

  公开（公告）日：2017-07-20

  A method of treating cancer or a precancer condition in a mammal comprising administering a therapeutically effective amount of a homovanillyl sinapate analog or pharmacologically acceptable salt, solvate, ester, amide, clathrate, stereoisomer, enantiomer, prodrug or analog thereof, or a combination thereof.

  在哺乳动物中治疗癌症或癌前病变的方法包括给予治疗有效量的异丙基肉桂酸酯类似物或药理学上可接受的盐、溶剂化合物、酯、酰胺、包合物、立体异构体、对映异构体、前药或其类似物，或其组合。
• Method for modulating metabolism
  申请人：Brightseed, Inc.

  公开号：US11173136B2

  公开（公告）日：2021-11-16

  A method for modulating metabolism is provided which includes the step of providing a consumable composition including an extract containing a compound of Formula I to a subject in need thereof thereby modulating the subject's metabolism and addressing the underlying pathogenesis of metabolic disorders, such as nonalcoholic fatty liver disease, nonalcoholic steatohepatitis and type II diabetes mellitus.

  本发明提供了一种调节新陈代谢的方法，该方法包括以下步骤：向有需要的受试者提供一种可消耗的组合物，该组合物包括含有式 I 化合物的提取物，从而调节受试者的新陈代谢，解决代谢紊乱的潜在发病机制，如非酒精性脂肪肝、非酒精性脂肪性肝炎和 II 型糖尿病。
• Method for improving digestive health
  申请人：Brightseed, Inc.

  公开号：US11382880B2

  公开（公告）日：2022-07-12

  Disclosed herein are methods for improving digestive health by providing a consumable composition. Some embodiments provided include, for example, administering a compound of Formula (I) or compound of Formula (II). Some embodiments provide the composition is formulated as a dietary supplement, food ingredient or additive, a medical food, nutraceutical or pharmaceutical composition.

  本文公开了通过提供一种可消费组合物来改善消化系统健康的方法。所提供的一些实施方案包括，例如，施用式（I）化合物或式（II）化合物。一些实施方案提供的组合物被配制成膳食补充剂、食品成分或添加剂、医用食品、营养保健品或药物组合物。
• 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.
• METHOD FOR MODULATING METABOLISM
  申请人：Brightseed, Inc.

  公开号：US20200368186A1

  公开（公告）日：2020-11-26

  A method for modulating metabolism is provided which includes the step of providing a consumable composition including an extract containing a compound of Formula Ito a subject in need thereof thereby modulating the subject's metabolism and addressing the underlying pathogenesis of metabolic disorders, such as nonalcoholic fatty liver disease, nonalcoholic steatohepatitis and type II diabetes mellitus.