benzyl 17-((-)-N-cyclobutylmethyl)morphinan-3-yl 2,2,9,9-tetramethyldecanedioate | 1184177-69-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: benzyl 17-((-)-N-cyclobutylmethyl)morphinan-3-yl 2,2,9,9-tetramethyldecanedioate
• 英文别名: 10-O-benzyl 1-O-[(1R,9R,10R)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl] 2,2,9,9-tetramethyldecanedioate
• CAS: 1184177-69-2
• 化学式: C₄₂H₅₉NO₄
• 分子量: 641.935
• InChiKey: PJTRSVXDCXQUPF-KVDSRRFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 17-((-)-N-cyclobutylmethyl)morphinan-3-yl 2,2,9,9-tetramethyldecanedioate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 2,2,9,,9-tetramethyldecanedioic acid 10-((-)-N-cyclobutylmethylmorphinan-3-yl) ester
  参考文献：
  名称：

  Univalent and Bivalent Ligands of Butorphan: Characteristics of the Linking Chain Determine the Affinity and Potency of Such Opioid Ligands

  摘要：

  Bivalent morphinan compounds containing ester linkers were synthesized and their binding affinities at the mu, delta, and kappa opioid receptors determined. Addition of methyl groups adjacent to the hydrolytically labile ester linkage increased stability while only partially affecting binding affinity. The resulting bivalent ligands with optimized spacer length and structure show potent binding profiles with the most potent compound (4b), having K-i values of 0.47 nM for both the mu and kappa opioid receptors, and 4a, having K-i values of 0.95 and 0.62 nM for the mu and kappa receptors, respectively. Both 4a and 4b were partial agonists at the kappa and mu receptors in the [S-35]GTP gamma S binding assay.

  DOI：

  10.1021/jm900379p
• 作为产物：
  描述：

  、 butorphan 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 benzyl 17-((-)-N-cyclobutylmethyl)morphinan-3-yl 2,2,9,9-tetramethyldecanedioate
  参考文献：
  名称：

  Univalent and Bivalent Ligands of Butorphan: Characteristics of the Linking Chain Determine the Affinity and Potency of Such Opioid Ligands

  摘要：

  Bivalent morphinan compounds containing ester linkers were synthesized and their binding affinities at the mu, delta, and kappa opioid receptors determined. Addition of methyl groups adjacent to the hydrolytically labile ester linkage increased stability while only partially affecting binding affinity. The resulting bivalent ligands with optimized spacer length and structure show potent binding profiles with the most potent compound (4b), having K-i values of 0.47 nM for both the mu and kappa opioid receptors, and 4a, having K-i values of 0.95 and 0.62 nM for the mu and kappa receptors, respectively. Both 4a and 4b were partial agonists at the kappa and mu receptors in the [S-35]GTP gamma S binding assay.

  DOI：

  10.1021/jm900379p

文献信息

• Univalent and Bivalent Ligands of Butorphan: Characteristics of the Linking Chain Determine the Affinity and Potency of Such Opioid Ligands
  作者：Michael Decker、Brian S. Fulton、Bin Zhang、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm900379p

  日期：2009.12.10

  Bivalent morphinan compounds containing ester linkers were synthesized and their binding affinities at the mu, delta, and kappa opioid receptors determined. Addition of methyl groups adjacent to the hydrolytically labile ester linkage increased stability while only partially affecting binding affinity. The resulting bivalent ligands with optimized spacer length and structure show potent binding profiles with the most potent compound (4b), having K-i values of 0.47 nM for both the mu and kappa opioid receptors, and 4a, having K-i values of 0.95 and 0.62 nM for the mu and kappa receptors, respectively. Both 4a and 4b were partial agonists at the kappa and mu receptors in the [S-35]GTP gamma S binding assay.