N-(4-hydroxyphenethyl)-3-phenylpropanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxyphenethyl)-3-phenylpropanamide
• 英文别名: 3-phenylpropionyltyramine；N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropanamide
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: PJGJZERHTUMFLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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)-3-phenylpropanamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropylamine
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Bis(phenylalkyl)amines:  Potent Subtype-Selective Inhibitors of N-Methyl-d-aspartate Receptors

  摘要：

  A series of bis(phenylalkyl)amines, structural analogues of ifenprodil and nylidrin, were synthesized and tested for antagonism of N-methyl-D-aspartate (NMDA) receptors. Potency and subunit selectivity were assayed by electrical recordings in Xenopus oocytes expressing three binary combinations of cloned rat NMDA receptor subunits: NR1A expressed in combination with either NR2A, NR2B, or NR2C. The bis(phenylalkyl)amines were selective antagonists of NR1A/2B receptors. Assayed under steady-state conditions, the most potent of these, N-[2-(4-hydroxyphenyl)ethyl]-5-phenylpentylamine hydrochloride (20), has an IC50 value of 8 nM and > 1000-fold selectivity with respect to NR1A/2A and NR1A/2C receptors. The structure-activity relationship of the bis(phenylalkyl)amine series indicates that the piperidine ring and alkyl chain substitutions common to NR2B-selective antagonists such as ifenprodil, CP 101,606, and Ro 25-6981 are not necessary to generate potent and selective ligands. The primary determinants of potency are the phenolic OH group, acting as a hydrogen bond donor, the distance between the two rings, and an electrostatic interaction between the receptor and the basic nitrogen atom. This study provides a framework for designing structurally novel NR2B-selective antagonists which may be useful for treatment of a variety of neurological disorders.

  DOI：

  10.1021/jm980235+
• 作为产物：
  描述：

  对羟基苯乙胺 、 2-氧代-4-苯基丁酸 在 叔丁基过氧化氢 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以75%的产率得到N-(4-hydroxyphenethyl)-3-phenylpropanamide
  参考文献：
  名称：

  氢过氧化物介导的α-酮酸脱羧能够实现胺的化学选择性酰化。

  摘要：

  迄今为止，酰胺键形成的策略，即有机合成中最基本和最重要的转变之一，主要集中在脱水反应上。在本文中，我们报告并证明了通过使用廉价的叔丁基氢过氧化物（TBHP）来生产α-酮酸的新型脱羧酰胺化技术的实用性，该技术的特点是收率高，底物范围宽，反应条件温和以及独特的化学选择性。这些特征使得能够在保留立体化学信息的情况下从氨基酸衍生的α-酮酸合成肽。

  DOI：

  10.1002/chem.201904717

文献信息

• COMPOUNDS FOR THE TREATMENT OF AIDS AND OTHER VIRAL DISEASES
  申请人：Kaplan Eliahu

  公开号：US20100331383A1

  公开（公告）日：2010-12-30

  The present invention provides methods for treating Acquired Immunodeficiency Syndrome (AIDS) and other viral diseases and Human Immunodeficiency Virus (HIV) related infections by administering one or more compounds of formula I: wherein: the dotted line represents a single or a double bond; and R 1 and R 2 are the same or different and independently of each other represent —CH 2 OH, —CH 2 OR 4 , —CH(OH)CH 3 , —CH(OR 4 )CH 3 or a group represented by the formula: or salts or hydrates thereof in a carrier which minimizes micellar formation or van der Waals attraction of molecules of said compound. The invention also provides S enantiomeric forms of such compounds which possess the ability to inhibit cell growth whilst being of low toxicity to such cells and methods of making such compounds.

  本发明提供了一种治疗获得性免疫缺陷综合症（艾滋病）和其他病毒性疾病以及人类免疫缺陷病毒（HIV）相关感染的方法，该方法通过在最小化分子聚集或范德华引力的载体中给予式I中的一个或多个化合物治疗，其中：虚线代表单键或双键；R1和R2相同或不同，且独立地代表—CH2OH，—CH2OR4，—CH（OH）CH3，—CH（OR4）CH3或由公式表示的基团：或其盐或水合物。本发明还提供了具有抑制细胞生长能力且对这些细胞毒性较低的这种化合物的S对映体形式以及制备这种化合物的方法。
• PHENYL-CONTAINING N-ACYL AMINE AND AMINOACID DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, A PHARMACEUTICAL COMPOSITION AND THE USE THEREOF
  申请人：Obschestvo S Ogranichennoi Otvetstennostiyu "Pharmenterprises"

  公开号：EP1876169A1

  公开（公告）日：2008-01-09

  The present invention relates to novel phenyl-N-acyl derivatives of biogenic amines and amino acids of general formula (I) as cyclooxynease inhibitors, possessing analgetic and anti-inflammatory properties and devoid of side effects in particular ulcerogeneity and pro-spasmodic actions, as well as capability to potentiate effect of other analgetics, and possessing in addition antihypoxic, antidepressant and anti-Parkinsonistic action; as well as to the processes for the preparation novel and known phenyl-N-acyl derivatives of biogenic amines, to a pharmaceutical composition and to an agent comprising compounds of general formula (I) as well as to use thereof and a method of treating.

  本发明涉及作为环氧化酶抑制剂的通式（I）生物胺和氨基酸的新型苯基-N-酰基衍生物，该衍生物具有镇痛和抗炎特性，无副作用，特别是无溃疡性和促痉挛作用，并能增强其他镇痛药的效果，此外还具有抗缺氧、抗抑郁和抗帕金森病作用；以及生物胺的新型和已知苯基-N-酰基衍生物的制备工艺、药物组合物和包含通式（I）化合物的制剂及其用途和治疗方法。
• 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.
• Phenyl-containing n-acyl amine and aminoacid derivatives, methods for the production thereof, a pharmaceutical composition and the use thereof
  申请人：Nebolsin Vladimir Evgenievich

  公开号：US20090111874A1

  公开（公告）日：2009-04-30

  The present invention relates to novel phenyl-N-acyl derivatives of biogenic amines and amino acids of general formula (I) as cyclooxynease inhibitors, possessing analgetic and anti-inflammatory properties and devoid of side effects in particular ulcerogeneity and pro-spasmodic actions, as well as capability to potentiate effect of other analgetics, and possessing in addition antihypoxic, antidepressant and anti-Parkinsonistic action; as well as to the processes for the preparation novel and known phenyl-N-acyl derivatives of biogenic amines, to a pharmaceutical composition and to an agent comprising compounds of general formula (I) as well as to use thereof and a method of treating.
• Novel compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection
  申请人：Kaplan Eliahu

  公开号：US20100069454A1

  公开（公告）日：2010-03-18

  The present invention provides compounds, pharmaceutical compositions and methods for treating, immuno-allergical diseases, autoimmune diseases, and organ or tissue rejection following transplantation.