5,6-dihydroaaptamine | 85547-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,6-dihydroaaptamine
• 英文别名: dihydroaaptamine；dihydro-aaptamine；11,12-dimethoxy-2,6-diazatricyclo[7.3.1.05,13]trideca-1,3,5(13),9,11-pentaene
• CAS: 85547-23-5
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: JGWLCFPRHLKVFH-UHFFFAOYSA-N

物化性质

• 沸点：
  433.6±45.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  43.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十二酸酐 、 5,6-dihydroaaptamine 以 吡啶 为溶剂， 以42%的产率得到4-N-lauryldihydroaaptamine
  参考文献：
  名称：

  Structures and Cytotoxicity Relationship of Isoaaptamine and Aaptamine Derivatives

  摘要：

  A series of 9-O-acylisoaaptamine (3-14) and 4-N-acyl-dihydroaaptamine (16-19) derivatives have been prepared and evaluated for antitumor activity against murine P-388 and human tumor cells including KB16, A549, and HT-29 cell lines. All of compounds showed significant cytotoxicity against P-388 cells. Among them, compounds 9-11 showed potent activity as isoaaptamine (1). There was an apparent lack of linear relationship between cytotoxicity and carbon number of the side chain. The structure and activity relationship for these particular compounds are discussed.

  DOI：

  10.1021/np990156g
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 在 palladium on activated charcoal ammonium hydroxide 、 氢溴酸 、 氢气 、 硝酸 、 diborane(6) 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 xylene 为溶剂， 95.0 ℃ 、310.27 kPa 条件下， 反应 29.0h， 生成 5,6-dihydroaaptamine
  参考文献：
  名称：

  Synthesis of the marine alkaloids aaptamine and demethyloxyaaptamine and of the parent structure didemethoxyaaptamine

  摘要：

  DOI：

  10.1021/jo00380a024

文献信息

• A new total synthesis of aaptamine
  作者：Robert G. Andrew、Ralph A. Raphael

  DOI：10.1016/s0040-4020(01)87665-1

  日期：1987.1

  A new synthesis of the α-adrenoceptor blocker aaptamine (1) from the readily available 5-nitrovanillin is reported. An unusual intramolecular nucleophilic displacement of a nitro-group is described.

  据报道，从容易获得的5-硝基香兰素中合成了α-肾上腺素受体阻滞剂适体胺（1）。描述了硝基的不寻常的分子内亲核取代。
• Isolation and structure of aaptamine a novel heteroaromatic substance possessing α-blocking activity from the sea sponge
  作者：Hideshi Nakamura、Jun'ichi Kobayashi、Yasushi Ohizumi、Yoshimasa Hirata

  DOI：10.1016/s0040-4039(00)85893-1

  日期：1982.1

  A novel heteroaromatic substance, aaptamine possessing an α-adrenoceptor blocking activity has been isolated from the tropical sea sponge Aaptos aaptos and its structure has been determined to be 1 on the basis of spectral data and chemical degradation.

  从热带海海绵Aaptos aaptos中分离出一种具有α-肾上腺素受体阻断活性的新型杂芳族物质，Aaptamine，根据光谱数据和化学降解，确定其结构为1。
• Structures and Cytotoxicity Relationship of Isoaaptamine and Aaptamine Derivatives
  作者：Ya-Ching Shen、Tain-Tsair Lin、Jyh-Horng Sheu、Chang-Yih Duh

  DOI：10.1021/np990156g

  日期：1999.9.1

  A series of 9-O-acylisoaaptamine (3-14) and 4-N-acyl-dihydroaaptamine (16-19) derivatives have been prepared and evaluated for antitumor activity against murine P-388 and human tumor cells including KB16, A549, and HT-29 cell lines. All of compounds showed significant cytotoxicity against P-388 cells. Among them, compounds 9-11 showed potent activity as isoaaptamine (1). There was an apparent lack of linear relationship between cytotoxicity and carbon number of the side chain. The structure and activity relationship for these particular compounds are discussed.
• Synthesis of the marine alkaloids aaptamine and demethyloxyaaptamine and of the parent structure didemethoxyaaptamine
  作者：Jeffrey C. Pelletier、Michael P. Cava

  DOI：10.1021/jo00380a024

  日期：1987.2