N-(3,4-dihydroxyphenethyl)pivalamide | 42600-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(3,4-dihydroxyphenethyl)pivalamide
• 英文别名: NPiD；N-pivaloyl dopamine；N-<β-(3.4-Dihydroxyphenyl)ethyl>-2.2-dimethylpropionamid；N-[β-(3,4-Dihydroxyphenyl)-ethyl]-2,2-dimethylpropionamide；N-[beta-(3,4-Dihydroxyphenyl)-ethyl]-2,2-dimethylpropionamide；N-[2-(3,4-dihydroxyphenyl)ethyl]-2,2-dimethylpropanamide
• CAS: 42600-74-8
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: VWYOELKIAGDDBT-UHFFFAOYSA-N

物化性质

• 沸点：
  479.6±35.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dihydroxyphenethyl)pivalamide 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 3,4-di(benzyloxy)phenethylamine
  参考文献：
  名称：

  Multifunctional Ag@Fe2O3 yolk–shell nanoparticles for simultaneous capture, kill, and removal of pathogen

  摘要：

  我们通过Kirkendall效应将银和氧化铁纳米颗粒结合，制成了独特的Ag@Fe2O3蛋黄壳多功能纳米颗粒。经过使用葡萄糖的表面功能化后，Ag@Fe2O3-Glu缀合物表现出了高效的细菌捕获效率和强大的抗菌活性。Ag@Fe2O3蛋黄壳纳米结构可能提供一个独特的多功能平台，用于同时快速检测、捕获细菌以及安全的解毒治疗。

  DOI：

  10.1039/c1jm13691g
• 作为产物：
  描述：

  三甲基乙酸 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3,4-dihydroxyphenethyl)pivalamide
  参考文献：
  名称：

  Analyses of Synthetic N-Acyl Dopamine Derivatives Revealing Different Structural Requirements for Their Anti-inflammatory and Transient-Receptor-Potential-Channel-of-the-Vanilloid-Receptor-Subfamily-Subtype-1 (TRPV1)-Activating Properties

  摘要：

  We studied the chemical entities within N-octanoyl dopamine (NOD) responsible for the activation of transient-receptor-potential channels of the vanilloid-receptor subtype 1 (TRPV1) and inhibition of inflammation. The potency of NOD in activating TRPV1 was significantly higher compared with those of variants in which the ortho-dihydroxy groups were acetylated, one of the hydroxy groups was omitted (N-octanoyl tyramine), or the ester functionality consisted of a bulky fatty acid (N-pivaloyl dopamine). Shortening of the amide linker (Delta NOD) slightly increased its potency, which was further increased when the carbonyl and amide groups (Delta NODR) were interchanged. With the exception of Delta NOD, the presence of an intact catechol structure was obligatory for the inhibition of VCAM-1 and the induction of HO-1 expression. Because TRPV1 activation and the inhibition of inflammation by N-acyl dopamines require different structural entities, our findings provide a framework for the rational design of TRPV1 agonists with improved anti-inflammatory properties.

  DOI：

  10.1021/acs.jmedchem.8b00156

文献信息

• Substituted aryl and aralkyl amides in the treatment of parkinsonism
  申请人：Schering Corporation

  公开号：US03944675A1

  公开（公告）日：1976-03-16

  Amides having aromatic substituents of the formula: ##SPC1## Wherein R is an acyl radical derived from a carboxylic acid having from 3 to 20 carbon atoms, X and Y are members selected from the group consisting of hydrogen, fluoro, trifluoromethyl and hydroxy, and n is an integer selected from the group consisting of 0, 1 and 2, exhibit an effect upon the central nervous system.

  含有芳香基团的酰胺的化学式为：##SPC1## 其中，R是从含有3至20个碳原子的羧酸衍生的酰基，X和Y是从氢、氟、三氟甲基和羟基组成的成员中选择的，n是从0、1和2组成的整数中选择的，对中枢神经系统产生影响。
• COMPOUNDS FOR THE TREATMENT OF CANCER AND INFLAMMATORY DISEASE
  申请人：SHY Therapeutics LLC

  公开号：US20170174699A1

  公开（公告）日：2017-06-22

  Provided herein are compounds that inhibit the phosphorylation of MAPK and thus are useful in compositions and methods for treating cancer and inflammatory disease.

  本文提供了抑制MAPK磷酸化的化合物，因此可用于治疗癌症和炎症性疾病的组合物和方法。
• [EN] LIPOPHILIC DOPAMINE DERIVATIVES AND THEIR USE<br/>[FR] DÉRIVÉS DE DOPAMINE LIPOPHILES ET LEUR UTILISATION
  申请人：NOVALIQ GMBH

  公开号：WO2013034457A1

  公开（公告）日：2013-03-14

  The invention provides novel lipophilic dopamine derivatives with improved stability and physiological half-life. The compounds may be used for organ and tissue preservation during storage and transport, or in the pre-treatment of organ and tissue donor or recipients. Moreover, they may be used as therapeutic agents for the prevention or treatment of ischaemia-related pathological conditions.

  本发明提供了一种新型的亲脂性多巴胺衍生物，具有改善稳定性和生理半衰期的特点。这些化合物可用于在储存和运输期间进行器官和组织保护，或用于器官和组织供体或受体的预处理。此外，它们可以用作治疗剂，用于预防或治疗缺血相关的病理状况。
• Substituted aryl and aralkyl amides
  申请人：Schering Corporation

  公开号：US04053509A1

  公开（公告）日：1977-10-11

  Amides having aromatic substituents of the formula: ##STR1## wherein R is an acyl radical derived from a carboxylic acid having from 3 to 20 carbon atoms, X and Y are members selected from the group consisting of hydrogen, fluoro, trifluoromethyl and hydroxy, and n is an integer selected from the group consisting of 0, 1 and 2, exhibit an effect upon the central nervous system.

  具有芳香基取代基的酰胺的化学式为：##STR1## 其中R是来自具有3至20个碳原子的羧酸的酰基基团，X和Y是从氢，氟，三氟甲基和羟基组成的成员中选择的，n是从0，1和2组成的整数，表现出对中枢神经系统的影响。
• 3-Carbamoyl-2-Pyridone Derivative
  申请人：Ishizuka Natsuki

  公开号：US20080103139A1

  公开（公告）日：2008-05-01

  The present invention provides compounds having an agonistic activity to the cannabinoid receptor, which is represented by the formula (I): wherein R 1 is optionally substituted C1-C8 alkyl and the like; R 2 is C1-C6 alkyl; R 3 is C1-C6 alkyl and the like; or R 2 and R 3 taken together with may form an optionally substituted 5 to 10 membered non-aromatic carbon ring; R 4 is hydrogen and the like; G is a group selected from the groups shown by the formula an the like: wherein R 5 is hydrogen and the like; X 1 is a single bond and the like; X 2 is optionally substituted C1-C8 alkylene that may be replaced by one or two groups of —O—, or —N(R 6 )—, wherein R 6 is hydrogen and the like, and the like; X 3 is a single bond and the like; a pharmaceutically acceptable salt or a solvate thereof, and pharmaceutical compositions, atopic dermatitis treating agents, and anti-pruritus agents, especially anti-pruritus agents for oral used and for external application, which each contains the said compound as an active ingredient.

  本发明提供了具有激动大麻素受体的作用的化合物，其由式（I）表示：其中，R1是可选取的取代的C1-C8烷基等；R2是C1-C6烷基；R3是C1-C6烷基等；或R2和R3共同形成可选取代的5至10个成员的非芳香碳环；R4是氢等；G是由式等所示的基团中选取的基团：其中，R5是氢等；X1是单键等；X2是可选取代的C1-C8烷基，可以被一或两个-O-或-N（R6）-的基团替代，其中R6是氢等；X3是单键等；其药学上可接受的盐或其溶剂，以及制药组合物、治疗特应性皮炎的制剂和抗瘙痒剂，特别是口服和外用的抗瘙痒剂，每种制剂均以所述化合物为活性成分。