1-Benzyl-4-(cyclohexylmethylamino)piperidine-4-carboxamide | 1027430-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Benzyl-4-(cyclohexylmethylamino)piperidine-4-carboxamide
• CAS: 1027430-00-7
• 化学式: C₂₀H₃₁N₃O
• 分子量: 329.486
• InChiKey: AMCFYVLSVMYLTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Benzyl-4-(cyclohexylmethylamino)piperidine-4-carboxamide 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium hydride 、 sodium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 139.5h， 生成 Methyl 8-(t-butoxycarbonyl)-1-cyclohexylmethyl-4-keto-1,3,8-triazaspiro [4.5]decan-3-acetate
  参考文献：
  名称：

  Synthesis and Characterization of Pseudopeptide Bradykinin B2 Receptor Antagonists Containing the 1,3,8-Triazaspiro[4.5]decan-4-one Ring System

  摘要：

  A series of pseudopeptides containing alkyl-, cycloalkyl-, aryl-, and aralkyl-substituted 1,3,8-triazaspiro[4.5]decan-4-one-3-acetic acids as amino acid surrogates to replace the Pro(2)-Pro(3)-Gly(4)-Phe(5) section of the peptide bradykinin B2 receptor antagonist [Pro(3), Phe(5)]HOE 140 (D-Arg(0)-Arg(1)-Pro(2)-Pro(3)-Gly(4)-Phe(5)-Ser(6)-D-Tic(7)-Oic(8)-Arg(9)) were prepared. These psuedopeptides were examined in vitro for their B2 receptor affinities as well as for their ability to block bradykinin mediated actions in, vivo. Two compounds in particular, NPC 18521 (I) and NPC 18688 (V) were quite potent in these latter assays, indicating that a significant portion of this prototypical second generation decapeptide antagonist can be replaced with a more compact nonpeptide molecule.

  DOI：

  10.1021/jm950676i
• 作为产物：
  描述：

  1-Benzyl-4-(cyclohexylmethylamino)piperidine-4-carbonitrile 在 硫酸 作用下， 反应 20.0h， 生成 1-Benzyl-4-(cyclohexylmethylamino)piperidine-4-carboxamide
  参考文献：
  名称：

  Synthesis and Characterization of Pseudopeptide Bradykinin B2 Receptor Antagonists Containing the 1,3,8-Triazaspiro[4.5]decan-4-one Ring System

  摘要：

  A series of pseudopeptides containing alkyl-, cycloalkyl-, aryl-, and aralkyl-substituted 1,3,8-triazaspiro[4.5]decan-4-one-3-acetic acids as amino acid surrogates to replace the Pro(2)-Pro(3)-Gly(4)-Phe(5) section of the peptide bradykinin B2 receptor antagonist [Pro(3), Phe(5)]HOE 140 (D-Arg(0)-Arg(1)-Pro(2)-Pro(3)-Gly(4)-Phe(5)-Ser(6)-D-Tic(7)-Oic(8)-Arg(9)) were prepared. These psuedopeptides were examined in vitro for their B2 receptor affinities as well as for their ability to block bradykinin mediated actions in, vivo. Two compounds in particular, NPC 18521 (I) and NPC 18688 (V) were quite potent in these latter assays, indicating that a significant portion of this prototypical second generation decapeptide antagonist can be replaced with a more compact nonpeptide molecule.

  DOI：

  10.1021/jm950676i

文献信息

• Bradykinin antagonist pseudopeptide derivatives of substituted
  申请人：Scios Inc.

  公开号：US05610142A1

  公开（公告）日：1997-03-11

  Novel compounds with as few as three natural amino acids that incorporate a substituted 4-keto-1,3,8-triazaspiro[4.5]decan-3-alkanoyl bridge in place of selected fragments of peptidic bradykinin receptor antagonists are pseudopeptides with potent bradykinin receptor antagonist actions. These pseudopeptides and their pharmaceutical compositions are of benefit in treating conditions and diseases of mammals, including humans, in which an excess of bradykinin or a related kinin is produced endogenously or is received exogenously, for example via insect bite.

  这些小说化合物仅包含三种天然氨基酸，它们将肽类布雷金受体拮抗剂的部分片段替换为取代的4-酮基-1,3,8-三氮杂螺[4.5]癸烷-3-脂肪酰桥，是具有强效布雷金受体拮抗剂作用的伪肽。这些伪肽及其制药组合物对于治疗哺乳动物（包括人类）中自身产生过多布雷金或相关的激肽，或通过昆虫叮咬等外源性途径接收到过多激肽的情况和疾病具有益处。
• US5610142A
  申请人：——

  公开号：US5610142A

  公开（公告）日：1997-03-11