7-(4-chlorophenoxy)heptylamine | 200484-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 7-(4-chlorophenoxy)heptylamine
• 英文别名: 7-p-chlorophenoxyheptylamine；7-(4-Chlorophenoxy)-heptylamine；7-(4-chlorophenoxy)heptan-1-amine
• CAS: 200484-55-5
• 化学式: C₁₃H₂₀ClNO
• 分子量: 241.761
• InChiKey: LCJYGUAVGNUJGY-UHFFFAOYSA-N

物化性质

• 沸点：
  351.6±22.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯苯并咪唑 、 7-(4-chlorophenoxy)heptylamine 以 异戊醇 为溶剂， 反应 16.0h， 以78%的产率得到N-[7-(4-chlorophenoxy)heptyl]-1H-benzimidazol-2-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063
• 作为产物：
  描述：

  7-(4-chlorophenoxy)heptanenitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以46%的产率得到7-(4-chlorophenoxy)heptylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063

文献信息

• Derivatives of squaric acid with anti-proliferative activity
  申请人：GPC Biotech AG

  公开号：EP1674457B1

  公开（公告）日：2009-06-03
• Novel cyanoguanidines with potent oral antitumour activity
  作者：Charlotte Schou、Erik R. Ottosen、Hans Jørgen Petersen、Fredrik Björkling、Scilla Latini、Pernille V. Hjarnaa、Erik Bramm、Lise Binderup

  DOI：10.1016/s0960-894x(97)10152-4

  日期：1997.12

  4-Pyridyl cyanoguanidines with hydrophobic aromatic side chains showed potent antiproliferative activity in the human breast and lung cancer cell lines MCF-7, NYH and H460. In vivo, treatment with N-(6-chlorophenoxyhexyl)-N'-cyano-N "-4-pyridylguanidine (18, 20 mg/kg/day po.), gave a complete remission of tumours in a model of NYH inoculated nude mice. (C) 1997 Elsevier Science Ltd.
• Synthesis and in vitro cytotoxicity of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives
  作者：Jyh-Haur Chern、Kak-Shan Shia、Chung-Ming Chang、Chung-Chi Lee、Yen-Chun Lee、Chia-Liang Tai、Ying-Ting Lin、Chih-Shiang Chang、Huan-Yi Tseng

  DOI：10.1016/j.bmcl.2003.12.073

  日期：2004.3

  A series of 5-substituted 2-eyanoimino-4-imidazodinone and 2-eyanoimino-4-pyrimidinone derivatives were synthesized and their anticancer cytotoxicity were evaluated in in vitro assay. It was found that the bulky aryl functionality in the 5-position of the 2-cyanoimino-4-imidazolidinone compounds was essential for the cytotoxicity of these heterocyclic compounds. Some of the derivatives exhibited modest cytotoxicity against a variety of cancer cell lines. One of the derivatives, [1-[6-(4-chlorophenoxy)hexyl]-5-oxo-4-phenyl-3-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethanenitrile (Compound 11), exhibited the most potent cytotoxic activity with IC50 in the nanomolar range. The cytotoxicity of these derivatives was selection with no apparent toxic effect toward normal fibroblasts. (C) 2003 Elsevier Ltd. All rights reserved.
• CYANOAMIDINES AS CELL PROLIFERATION INHIBITORS
  申请人：LEO PHARMACEUTICAL PRODUCTS LTD. A/S(LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB)

  公开号：EP0984940A1

  公开（公告）日：2000-03-15
• US5696140A
  申请人：——

  公开号：US5696140A

  公开（公告）日：1997-12-09