N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropylamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(4-hydroxyphenyl)ethyl]-3-phenylpropylamine
• 英文别名: 4-[2-(3-Phenyl-propylamino)-ethyl]-phenol；4-[2-(3-phenylpropylamino)ethyl]phenol
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: SJSNYEZWGGSNKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-苯基丙酸 在 lithium aluminium tetrahydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 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+

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。
• [EN] COMPOUNDS FOR TREATING AIDS AND OTHER DISEASES<br/>[FR] AMELIORATIONS APPORTEES A DES COMPOSES DESTINES A ETRE UTILISES DANS LE TRAITEMENT DU SIDA OU D'AUTRES MALADIES VIRALES ET INFECTIONS ASSOCIEES AU VIH ET COMPOSITIONS CONTENANT CES COMPOSES, METHODES DE TRAITEMENT DE CES MALADIES ET DE CES INFECTIONS
  申请人：NEW ERA BIOTECH LTD

  公开号：WO2005092305A3

  公开（公告）日：2006-03-02
• [EN] COMPOUNDS FOR USE IN THE TREATMENT OF AUTOIMMUNE DISEASES, IMMUNO-ALLERGICAL DISEASES AND ORGAN OR TISSUE TRANSPLANTATION REJECTION<br/>[FR] NOUVEAUX COMPOSES DESTINES AU TRAITEMENT DES MALADIES AUTO-IMMUNES, DES MALADIES IMMUNO-ALLERGIQUES ET DES REJETS EN CAS DE GREFFES D'ORGANES OU DE TISSUS
  申请人：NEW ERA BIOTECH LTD

  公开号：WO2004031129A3

  公开（公告）日：2004-07-15
• COMPOUNDS FOR USE IN THE TREATMENT OF AUTOIMMUNE DISEASES, IMMUNO-ALLERGICAL DISEASES AND ORGAN OR TISSUE TRANSPLANTATION REJECTION
  申请人：Novaremed Ltd.

  公开号：EP1546088B1

  公开（公告）日：2014-12-17
• COMPOUNDS FOR TREATMENT OF AIDS AND OTHER DISEASES
  申请人：Novaremed Ltd.

  公开号：EP1750691B1

  公开（公告）日：2016-08-10