6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine | 130178-43-7

• 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: 6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine
• 英文别名: 6β-(5'-Nitro-2'-pyridyldithio)deoxydihydromorphine；(4R,4aR,7R,7aR,12bS)-3-methyl-7-[(5-nitropyridin-2-yl)disulfanyl]-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
• CAS: 130178-43-7
• 化学式: C₂₂H₂₃N₃O₄S₂
• 分子量: 457.574
• InChiKey: RAEKUJQUZFRYFZ-ZCYBMSBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine 在 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of an opioid receptor probe: Mode of binding of S-activated (-)-6.BETA.-sulfhydryldihydromorphine with the SH group in the .MU.-opioid receptor.

  摘要：

  合成了一种 S 活化的巯基吗啡衍生物，并证明了它通过二硫键与μ-阿片受体的连接。

  DOI：

  10.1248/cpb.38.1438
• 作为产物：
  描述：

  双氢吗啡 在 氢氧化钾 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 6-β-<5-nitro-2-pyridinesulfenyl>thio-dihydromorphine
  参考文献：
  名称：

  Design and synthesis of an opioid receptor probe: Mode of binding of S-activated (-)-6.BETA.-sulfhydryldihydromorphine with the SH group in the .MU.-opioid receptor.

  摘要：

  合成了一种 S 活化的巯基吗啡衍生物，并证明了它通过二硫键与μ-阿片受体的连接。

  DOI：

  10.1248/cpb.38.1438

文献信息

• Ligand recognition in μ opioid receptor: experimentally based modeling of μ opioid receptor binding sites and their testing by ligand docking
  作者：Takeshi Sagara、Hiromu Egashira、Mikako Okamura、Ikuo Fujii、Yasuyuki Shimohigashi、Ken Kanematsu

  DOI：10.1016/s0968-0896(96)00219-2

  日期：1996.12

  For three-dimensional understanding of the mechanisms that control potency and selectivity of the ligand binding at the atomic level, we have analysed opioid receptor-ligand interaction based on the receptor's 3D model. As a first step, we have constructed molecular models for the multiple opioid receptor subtypes using bacteriorhodopsin as a template. The S-activated dihydromorphine derivatives should serve as powerful tools in mapping the three-dimensional structure of the mu opioid receptor, including the nature of the agonist-mediated conformational change that permits G protein-coupling to 'second messenger' effector molecules, and in identifying specific ligand-binding contacts with the mu opioid receptor. The analyses of the interactions of some opioid ligands with the predicted ligand binding sites are consistent with the results of the affinity labeling experiments. Copyright (C) 1996 Elsevier Science Ltd
• Design and synthesis of an opioid receptor probe: Mode of binding of S-activated (-)-6.BETA.-sulfhydryldihydromorphine with the SH group in the .MU.-opioid receptor.
  作者：Ken KANEMATSU、Ryo NAITO、Yasuyuki SHIMOHIGASHI、Motonori OHNO、Tomio OGASAWARA、Masayasu KURONO、Kunio YAGI

  DOI：10.1248/cpb.38.1438

  日期：——

  An S-activated sulfhydrylmorphine derivative was synthesized, and its linking to the μ-opioid receptor through a disulfide bond was demonstrated.

  合成了一种 S 活化的巯基吗啡衍生物，并证明了它通过二硫键与μ-阿片受体的连接。