(S)-3-(N-phenylpiperazin-4-ylcarbonyl)-7-(1-naphthalenesulfonyloxy)-1,2,3,4-tetrahydroisoquinoline | 271248-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3-(N-phenylpiperazin-4-ylcarbonyl)-7-(1-naphthalenesulfonyloxy)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: [(3S)-3-(4-phenylpiperazine-1-carbonyl)-1,2,3,4-tetrahydroisoquinolin-7-yl] naphthalene-1-sulfonate
• CAS: 271248-04-5
• 化学式: C₃₀H₂₉N₃O₄S
• 分子量: 527.644
• InChiKey: NDXFSRRICJRMEO-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异喹啉-5-磺酰氯 、 (S)-3-(N-phenylpiperazin-4-ylcarbonyl)-7-(1-naphthalenesulfonyloxy)-1,2,3,4-tetrahydroisoquinoline 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 [(3S)-2-isoquinolin-5-ylsulfonyl-3-(4-phenylpiperazine-1-carbonyl)-3,4-dihydro-1H-isoquinolin-7-yl] naphthalene-1-sulfonate
  参考文献：
  名称：

  Synthesis of conformationally constrained analogues of KN62, a potent antagonist of the P2X 7 -receptor

  摘要：

  Conformationally constrained analogues of KN62 containing 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid with S configuration in position 3 were synthesized and their antagonist activities were tested on human macrophage cells. While KN62 is a potent antagonist of the P2X(7) receptor, these analogues were inactive as antagonists and only one compound showed appreciable activity as P2X(7) antagonist, which was 30 times weaker than that reported for KN62. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00083-4
• 作为产物：
  描述：

  (S)-2-benzyloxycarbonyl-3-(N-phenylpiperazin-4-ylcarbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline 在 碘代三甲硅烷 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 23.25h， 生成 (S)-3-(N-phenylpiperazin-4-ylcarbonyl)-7-(1-naphthalenesulfonyloxy)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of conformationally constrained analogues of KN62, a potent antagonist of the P2X 7 -receptor

  摘要：

  Conformationally constrained analogues of KN62 containing 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid with S configuration in position 3 were synthesized and their antagonist activities were tested on human macrophage cells. While KN62 is a potent antagonist of the P2X(7) receptor, these analogues were inactive as antagonists and only one compound showed appreciable activity as P2X(7) antagonist, which was 30 times weaker than that reported for KN62. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00083-4

文献信息

• Baraldi, Pier Giovanni; Makaeva, Rimma; Pavani, Maria Giovanna, Arzneimittel-Forschung/Drug Research, 2002, vol. 52, # 4, p. 273 - 285
  作者：Baraldi, Pier Giovanni、Makaeva, Rimma、Pavani, Maria Giovanna、Del Carmen Nunez, Maria、Spalluto, Giampiero、Moro, Stefano、Falzoni, Simonetta、Di Virgilio, Francesco、Romagnoli, Romeo

  DOI：——

  日期：——