1-苄基-3-[(4-羟基-3-甲氧基苯基)甲基]硫脲 | 921766-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-苄基-3-[(4-羟基-3-甲氧基苯基)甲基]硫脲
• 英文名称: 1-benzyl-3-(4-hydroxy-3-methoxybenzyl)-thiourea
• 英文别名: N-Benzyl-N'-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea；1-benzyl-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea
• CAS: 921766-27-0
• 化学式: C₁₆H₁₈N₂O₂S
• 分子量: 302.397
• InChiKey: OJNZZJNMNYWUHR-UHFFFAOYSA-N

物化性质

• 沸点：
  485.4±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  85.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-苄基-3-[(4-羟基-3-甲氧基苯基)甲基]硫脲
  参考文献：
  名称：

  Design, synthesis, and computational validation of novel compounds selectively targeting HER2-expressing breast cancer

  摘要：

  Human epidermal growth factor receptor (HER) is a family of multidomain proteins that plays important role in the regulation of several biological functions. HER2 is a member of HER that is highly presented in breast cancer cells. Here, we designed and synthesized a series of diaryl urea/thiourea compounds. The compounds were tested on HER2+ breast cancer cells including MCF-7 and SkBr3, compared to HER2- breast cancer cells including MDA-MB-231 and BT-549. Only compounds 12-14 at 10 µM showed selective anti-proliferative activity against MCF-7 and SkBr3 by 65-79%. Compounds 12-14 showed >80% inhibition of the intracellular kinase domain of HER2. The results obtained indicated that compounds 12-14 are selectively targeting HER2+ cells. The IC50 of compound 13 against MCF-7 and SkBR3 were 1.3 ± 0.009 and 0.73 ± 0.03 µM, respectively. Molecular docking and MD simulations (50 ns) were carried out, and their binding free energies were calculated. Compounds 12-14 formed strong hydrogen bond and pi-pi stacking interactions with the key residues Thr862 and Phe864. 3DQSAR model confirmed the role of 3-bromo substituent of pyridine ring and 4-chloro substituent of phenyl ring in the activity of the compounds. In conclusion, novel compounds, particularly 13 were developed selectively against HER2-expressing/overexpressing breast cancer cells including MCF7 and SkBr3.

  DOI：

  10.1016/j.bmcl.2020.127658

文献信息

• FLAVOUR MODULATING SUBSTANCES
  申请人：Winkel Chris

  公开号：US20100129515A1

  公开（公告）日：2010-05-27

  The present invention in a first aspect relates to flavour modulation in foodstuffs, beverages, tobacco products and oral care products, using a flavour modulating substance selected from the group represented by formula (I), edible salts thereof and edible esters thereof. It has been found that these substances are capable imparting highly desirable taste attributes in the products they are incorporated in. In addition said flavour modulating substances are capable of modulating and complementing, the sensory impact of other, taste imparting, substances. Thus, the present substances are advantageously applied in flavour compositions, foodstuffs, tobacco products and oral care products. Typical examples of flavour modulating substances according to the present invention include N-vanillyl urea, N-vanillyl thiourea, N-vanillyl guanidine, N-isovanillyl urea, N-(3-ethoxy-4-hydroxybenzyl) urea, N-(3,4 dimethoxybenzyl) urea, N,N′-divanillyl urea, N,N′-divanillyl thiourea, N-octyl-N′-vanillyl urea, N-octyl-N′-vanillyl thiourea, N-hexyl-N′-vanillyl urea, N-hexyl-N′-vanillyl thiourea, N-decyl-N′-vanillyl urea, N-decyl-N′-vanillyl thiourea, N-benzyl-N′-vanillyl urea, N-benzyl-N′-vanillyl thiourea, edible salts thereof and edible esters thereof.

  本发明在第一方面涉及使用从式(I)所代表的化合物组中选择的调味调节物质、其可食用盐和可食用酯，对食品、饮料、烟草制品和口腔护理产品中的味道进行调节。已经发现这些物质能够在它们被加入的产品中赋予高度可取的口感特性。此外，所述调味调节物质能够调节和补充其他具有口感影响的物质的感官影响。因此，本发明的物质优点地应用于调味组合物、食品、烟草制品和口腔护理产品中。根据本发明的典型的调味调节物质包括N-香草基尿素，N-香草基硫脲，N-香草基胍，N-异香草基尿素，N-(3-乙氧基-4-羟基苯基)尿素，N-(3,4-二甲氧基苯基)尿素，N,N'-二香草基尿素，N,N'-二香草基硫脲，N-辛基-N'-香草基尿素，N-辛基-N'-香草基硫脲，N-己基-N'-香草基尿素，N-己基-N'-香草基硫脲，N-癸基-N'-香草基尿素，N-癸基-N'-香草基硫脲，N-苄基-N'-香草基尿素，N-苄基-N'-香草基硫脲，其可食用盐和可食用酯。
• SALTY TASTE ENHANCER
  申请人：AJINOMOTO CO., INC.

  公开号：US20140004243A1

  公开（公告）日：2014-01-02

  The present invention provides a compound having a salty taste enhance activity, and a salty taste enhancer containing the compound, and the like. The present invention relates to a salty taste enhancer for a food or drink, which contains a compound represented by the following formula: wherein each symbol is as defined in the specification, or an edible salt thereof.

  本发明提供了一种具有增强咸味活性的化合物，以及含有该化合物的增强咸味剂等。本发明涉及一种用于食品或饮料的增强咸味剂，其包含下式所示的化合物：其中每个符号如规范中所定义，或其可食用盐。
• N-VANILLYL UREA DERIVATIVES AS FLAVOUR MODULATING SUBSTANCES
  申请人：Quest International Services B.V.

  公开号：EP1915063A2

  公开（公告）日：2008-04-30
• [EN] FLAVOUR MODULATING SUBSTANCES<br/>[FR] SUBSTANCES MODULANT LA SAVEUR
  申请人：QUEST INT SERV BV

  公开号：WO2007013811A2

  公开（公告）日：2007-02-01

  [EN] The present invention in a first aspect relates to flavour modulation in foodstuffs, beverages, tobacco products and oral care products, using a flavour modulating substance selected from the group represented by formula (I), edible salts thereof and edible esters thereof. It has been found that these substances are capable imparting highly desirable taste attributes in the products they are incorporated in. In addition said flavour modulating substances are capable of modulating and complementing, the sensory impact of other, taste imparting, substances. Thus, the present substances are advantageously applied in flavour compositions, foodstuffs, tobacco products and oral care products. Typical examples of flavour modulating substances according to the present invention include N-vanillyl urea, N- vanillyl thiourea, N-vanillyl guanidine, N-isovanillyl urea, N-(3-ethoxy-4-hydroxybenzyl) urea, N-(3,4 dimethoxybenzyl) urea, N,N'-divanillyl urea, N,N'-divanillyl thiourea, N-octyl- N'-vanillyl urea, N-octyl-N'-vanillyl thiourea, N-hexyl-N'-vanillyl urea, N-hexyl-N'- vanillyl thiourea, N-decyl-N'-vanillyl urea, N-decyl-N'-vanillyl thiourea, N-benzyl-N'- vanillyl urea, N-benzyl-N'-vanillyl thiourea, edible salts thereof and edible esters thereof.
  [FR] Selon un premier aspect, l'invention concerne la modulation de la saveur dans des aliments, des boissons, des produits du tabac et des produits d'hygiène bucco-dentaire au moyen d'une substance modulant la saveur sélectionnée dans le groupe représenté par la formule (I), de sels comestibles et d'esters comestibles de ladite substance. Il a été découvert que ces substances sont capables de conférer des attributs de goût hautement souhaitables à des produits auxquels lesdites substances sont incorporées. En outre, ces substances modulant la saveur sont capables de moduler et de compléter l'impact sensoriel d'autres substances conférant un certain goût. Ainsi, lesdites substances sont avantageusement utilisées dans des compositions sapides, des aliments, des produits du tabac et des produits d'hygiène bucco-dentaire. Parmi des exemples typiques de substances modulant la saveur selon ladite invention figurent la N-vanillyl urée, la N-vanillyl thiourée, la N-vanillyl guanidine, la N-isovanillyl urée, la N-(3-éthoxy-4-hydroxybenzyl) urée, la N-(3,4 diméthoxybenzyl) urée, la N,N'-divanillyl urée, la N,N'-divanillyl thiourée, la N-octyl-N'-vanillyl urée, la N-octyl-N'-vanillyl thiourée, la N-hexyl-N'-vanillyl urée, la N-hexyl-N'-vanillyl thiourée, la N-décyl-N'-vanillyl urée, la N-décyl-N'-vanillyl thiourée, la N-benzyl-N'-vanillyl urée, la N-benzyl-N'-vanillyl thiourée, des sels comestibles et esters comestibles de ces derniers.
• [EN] N-VANILLYL UREA DERIVATIVES AS FLAVOUR MODULATING SUBSTANCES<br/>[FR] SUBSTANCES MODULANT LA SAVEUR
  申请人：QUEST INT SERV BV

  公开号：WO2007013811A3

  公开（公告）日：2007-05-10

  [EN] The present invention in a first aspect relates to flavour modulation in foodstuffs, beverages, tobacco products and oral care products, using a flavour modulating substance selected from the group represented by formula (I), edible salts thereof and edible esters thereof. It has been found that these substances are capable imparting highly desirable taste attributes in the products they are incorporated in. In addition said flavour modulating substances are capable of modulating and complementing, the sensory impact of other, taste imparting, substances. Thus, the present substances are advantageously applied in flavour compositions, foodstuffs, tobacco products and oral care products. Typical examples of flavour modulating substances according to the present invention include N-vanillyl urea, N- vanillyl thiourea, N-vanillyl guanidine, N-isovanillyl urea, N-(3-ethoxy-4-hydroxybenzyl) urea, N-(3,4 dimethoxybenzyl) urea, N,N'-divanillyl urea, N,N'-divanillyl thiourea, N-octyl- N'-vanillyl urea, N-octyl-N'-vanillyl thiourea, N-hexyl-N'-vanillyl urea, N-hexyl-N'- vanillyl thiourea, N-decyl-N'-vanillyl urea, N-decyl-N'-vanillyl thiourea, N-benzyl-N'- vanillyl urea, N-benzyl-N'-vanillyl thiourea, edible salts thereof and edible esters thereof.
  [FR] Selon un premier aspect, l'invention concerne la modulation de la saveur dans des aliments, des boissons, des produits du tabac et des produits d'hygiène bucco-dentaire au moyen d'une substance modulant la saveur sélectionnée dans le groupe représenté par la formule (I), de sels comestibles et d'esters comestibles de ladite substance. Il a été découvert que ces substances sont capables de conférer des attributs de goût hautement souhaitables à des produits auxquels lesdites substances sont incorporées. En outre, ces substances modulant la saveur sont capables de moduler et de compléter l'impact sensoriel d'autres substances conférant un certain goût. Ainsi, lesdites substances sont avantageusement utilisées dans des compositions sapides, des aliments, des produits du tabac et des produits d'hygiène bucco-dentaire. Parmi des exemples typiques de substances modulant la saveur selon ladite invention figurent la N-vanillyl urée, la N-vanillyl thiourée, la N-vanillyl guanidine, la N-isovanillyl urée, la N-(3-éthoxy-4-hydroxybenzyl) urée, la N-(3,4 diméthoxybenzyl) urée, la N,N'-divanillyl urée, la N,N'-divanillyl thiourée, la N-octyl-N'-vanillyl urée, la N-octyl-N'-vanillyl thiourée, la N-hexyl-N'-vanillyl urée, la N-hexyl-N'-vanillyl thiourée, la N-décyl-N'-vanillyl urée, la N-décyl-N'-vanillyl thiourée, la N-benzyl-N'-vanillyl urée, la N-benzyl-N'-vanillyl thiourée, des sels comestibles et esters comestibles de ces derniers.