N-(1-phenethylpiperidin-4-yl)benzamide | 974-10-7

• 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-(1-phenethylpiperidin-4-yl)benzamide
• 英文别名: N-(1-phenethyl-piperidin-4-yl)-benzamide；1-Phenethyl-4-benzamidopiperidine；1-Phenethyl-4-benzamidopiperdine；1-Phenethyl-4-benzamino-piperidin；4-Benzamido-1-phenethylpiperidine；N-[1-(2-phenylethyl)piperidin-4-yl]benzamide
• CAS: 974-10-7
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: KJLLJXGBQYAIBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-phenethylpiperidin-4-yl)benzamide 在 盐酸 、 diborane(6) 作用下， 生成 N-benzyl-1-phenethylpiperidin-4-amine
  参考文献：
  名称：

  Structure-Activity Studies of Fentanyl

  摘要：

  报道了在苯环中带有对位取代基，苯甲基与苯基之间以亚甲基或双亚甲基分离的芬太尼类似物的制备，以及苯乙酰取代丙酰作为N-酰基取代物。虽然检测到的所有对位取代基都降低了大鼠的抗痛觉效力，但这种类似物中的大多数比吗啡更有效，而p-F、I和Me衍生物的活性仅比芬太尼低几倍。将苯甲基与苯分离会降低效力，而N-苯乙基类似物保持合理的活性（>吗啡）。所有苯乙酰类似物的效力都很低或无效。附加了可能遇到的“设计药物”的类似物的质谱诊断细节。

  DOI：

  10.1111/j.2042-7158.1988.tb05318.x
• 作为产物：
  描述：

  N-(2-苯乙基)-4-哌啶酮 在 羟胺 、 sodium 、 三乙胺 作用下， 以 乙醇 、 异戊醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 N-(1-phenethylpiperidin-4-yl)benzamide
  参考文献：
  名称：

  [EN] SMALL MOLECULE ADRENORECEPTOR ANTAGONISTS AND USES THEREOF
  [FR] ANTAGONISTES D'ADRÉNORÉCEPTEUR À PETITES MOLÉCULES ET LEURS UTILISATIONS

  摘要：

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a piperdinyl-formamide (or similar) structure which function as adrenoreceptor antagonists, and their use as therapeutics for the treatment and/or prevention of pain and related conditions. In addition, the present invention provides compositions comprising a mixture of opioid receptor agonist compounds and such adrenoreceptor antagonists for the treatment and/or prevention of pain and related conditions.

  公开号：

  WO2023133135A2

文献信息

• Pharmaceutical compositions and methods of treating hypertension
  申请人：John Wyeth & Brother Limited

  公开号：US04029801A1

  公开（公告）日：1977-06-14

  Pharmaceutical compositions containing a group of heterocyclic compounds and their use in treatment of disorders and diseases of the cardiovascular system and/or in the treatment of superficial and deep allergic phenomena is described. These compounds used in the composition and/or methods are piperidine compounds linked by the nitrogen atom to a substituted or unsubstituted cycloalkyl, aryl or heterocyclic radical through the intermediary of a group selected from a lower-alkylene radical, a monoketo lower-alkylene radical or a hydroxy-lower-alkylene radical, or a bivalent radical of the formula --NH.CO.(CH.sub.2).sub.n -- where n is 1, 2 or 3, ##STR1## or --0-(lower-alkylene)--. The piperidine ring is further substituted by an acylamino residue.

  本发明描述了含有杂环化合物组的药物组合物及其在治疗心血管系统疾病和/或治疗浅表和深层过敏现象中的应用。这些组合物和/或方法中使用的化合物是哌啶化合物，通过氮原子与取代或未取代的环烷基、芳基或杂环基团相连，中间通过一个选自低级烷叉基、单酮低级烷叉基或羟基低级烷叉基的基团，或一个二价基团，其公式为--NH.CO.(CH.sub.2).sub.n --，其中n为1、2或3，##STR1##或--O-(低级烷叉基)--。哌啶环进一步被酰胺基残基取代。
• Heterocyclic compounds
  申请人：John Wyeth & Brother Limited

  公开号：US03992389A1

  公开（公告）日：1976-11-16

  A group of heterocyclic compounds useful in the treatment of disorders and diseases of the cardiovascular system and/or in the treatment of superficial and deep allergic phenomena is described. These compounds are piperidine compounds linked by the nitrogen atom to a substituted or unsubstituted phenyl radical through the intermediary of a group selected from a lower-alkylene radical, a mono-keto lower alkylene radical or a hydroxy-lower-alkylene radical, or a bivalent radical of the formula ##EQU1## or --O--(lower-alkylene)-. The piperidine rings are further substituted by a benzamido, substituted benzamido or cyclohexylcarboxamido residue.

  描述了一组在治疗心血管系统疾病和过敏现象方面有用的杂环化合物。这些化合物是通过氮原子与一个取代或未取代苯基通过选择自低烷基基团、单酮基低烷基基团或羟基-低烷基基团、或者公式##EQU1##的双价基团或--O--(低烷基)-连接的哌啶化合物。哌啶环进一步取代为苯甲酰胺基、取代苯甲酰胺基或环己基羧酰胺基残基。
• Substituted 1-arylethyl-4-acylaminopiperidine derivatives as opioid/alpha-adrenoreceptor modulators and method of their preparation
  申请人：The Arizona Board of Regents of Behalf of the University of Arizona

  公开号：US20160052882A1

  公开（公告）日：2016-02-25

  The invention provides compounds that bind with high affinities to the μ-, δ-and κ-opioid receptors and α 2 -adrenoreceptor. In addition to providing these compounds with novel pharmacological binding properties, the invention also describes detailed novel methods for the preparation of representative compounds and a scheme for the synthesis of related compounds that bind to the opioid receptors and/or α 2 -adrenoreceptor.

  该发明提供了与μ-, δ-和κ-阿片受体以及α2-肾上腺素受体高亲和力结合的化合物。除了提供这些具有新型药理学结合特性的化合物外，该发明还描述了制备代表性化合物的详细新方法，并提供了一种合成与阿片受体和/或α2-肾上腺素受体结合的相关化合物的方案。
• 1-arylalkyl-4-acylaminopiperidine compounds
  申请人：ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA

  公开号：US10617681B2

  公开（公告）日：2020-04-14

  The present invention provides a compound of the formula: wherein ring Z is a 5-, 6- or 7-membered ring; R1 is C1-10 alkyl, C1-10 haloalkyl, optionally substituted aralkyl, optionally substituted aryl, optionally substituted heteroaryl or optionally substituted heteroaralkyl; R2 is C1-10 alkylene; and Y is optionally substituted aryl, optionally substituted heteroaryl, or a moiety of the formula —C(═O)—X1, wherein X1 is —OR3 or —NR4R5, where each of R3, R4 and R5 is H or C1-10 alkyl. The present invention also provides a method for using compound of Formula I to treat a wide variety of clinical conditions.

  本发明提供了一种式化合物： 式中 环 Z 是 5、6 或 7 元环； R1 是 C1-10 烷基、C1-10 卤代烷基、任选取代的芳基、任选取代的芳烷基、任选取代的杂芳基或任选取代的杂烷基； R2 是 C1-10 亚烷基；以及 Y 是任选取代的芳基、任选取代的杂芳基或式-C(═O)-X1 的分子，其中 X1 是-OR3 或-NR4R5，其中 R3、R4 和 R5 各为 H 或 C1-10 烷基。 本发明还提供了一种使用式 I 化合物治疗多种临床疾病的方法。
• Substituted 1-arylalkyl-4-acylaminopiperidine compounds and methods of producing and using the same
  申请人：Arizona Board of Regents on Behalf of the University of Arizona

  公开号：US11440885B2

  公开（公告）日：2022-09-13

  The present invention provides using a substituted 1-arylalkyl-4-acylaminopiperidine compound of Formula I: to treat various clinical conditions including, but not limited to, hemorrhagic shock, nicotine withdrawal symptoms, gastrointestinal side effects of opioids, cancer therapy, epithelial wounds, herpes zoster infection, or opioid-induced pruritus. In compound of Formula I, R1 is C1-10 alkyl, C1-10 haloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; R2 is C1-6 alkylene; Y is optionally substituted aryl, optionally substituted heteroaryl, or a moiety of the formula —C(═O)—X1, wherein X1 is —OR3 or —NR4R5, where each of R3, R4 and R5 is H or C1-10 alkyl.

  本发明提供使用式 I 的取代 1-芳烷基-4-酰氨基哌啶化合物： 来治疗各种临床病症，包括但不限于失血性休克、尼古丁戒断症状、阿片类药物的胃肠道副作用、癌症治疗、上皮伤口、带状疱疹感染或阿片类药物诱发的瘙痒症。在式I化合物中，R1是C1-10烷基、C1-10卤代烷基、任选取代的芳基或任选取代的杂芳基；R2是C1-6亚烷基；Y是任选取代的芳基、任选取代的杂芳基或式-C(═O)-X1的分子，其中X1是-OR3或-NR4R5，其中R3、R4和R5各自是H或C1-10烷基。