1,6-bis(3-cyanophenoxy)hexane | 61947-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,6-bis(3-cyanophenoxy)hexane
• 英文别名: 3,3'-[Hexane-1,6-diylbis(oxy)]dibenzonitrile；3-[6-(3-cyanophenoxy)hexoxy]benzonitrile
• CAS: 61947-47-5
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: FFNMEPYUPRSQPD-UHFFFAOYSA-N

物化性质

• 沸点：
  505.8±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-bis(3-cyanophenoxy)hexane 在 盐酸 、 乙醇 、 氨 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 48.0h， 以95%的产率得到1,6-bis(benzamidine-3-oxy)hexane dihydrochloride
  参考文献：
  名称：

  Structure−Activity Study of Pentamidine Analogues as Antiprotozoal Agents

  摘要：

  Diamidine 1 (pentamidine) and 65 analogues (2-66) have been tested for in vitro antiprotozoal activities against Trypanosoma brucei rhodesiense, Plasmodium. falciparum, and Leishmania donovani, and for cytotoxicity against mammalian cells. Dications 32, 64, and 66 exhibited antitrypanosomal potencies equal or greater than melarsoprol (IC50 = 4 nM). Nine congeners (2-4, 12, 27, 30, and 64-66) were more active against P. falciparum than artemisinin (IC50 = 6 nM). Eight compounds (12, 32, 33, 44, 59, 62, 64, and 66) exhibited equal or better antileishmanial activities than 1 (IC50 = 1.8 mu M). Several congeners were more active than I in vivo, curing at least 2/4 infected animals in the acute mouse model of trypanosomiasis. The diimidazoline 66 was the most promising compound in the series, showing excellent in vitro activities and high selectivities against T. b. rhodesiense, P. falciparum, and L. donovani combined with high antitrypanosomal efficacy in vivo.

  DOI：

  10.1021/jm801547t
• 作为产物：
  描述：

  1,6-二溴己烷 、 3-氰基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以89%的产率得到1,6-bis(3-cyanophenoxy)hexane
  参考文献：
  名称：

  Structure−Activity Study of Pentamidine Analogues as Antiprotozoal Agents

  摘要：

  Diamidine 1 (pentamidine) and 65 analogues (2-66) have been tested for in vitro antiprotozoal activities against Trypanosoma brucei rhodesiense, Plasmodium. falciparum, and Leishmania donovani, and for cytotoxicity against mammalian cells. Dications 32, 64, and 66 exhibited antitrypanosomal potencies equal or greater than melarsoprol (IC50 = 4 nM). Nine congeners (2-4, 12, 27, 30, and 64-66) were more active against P. falciparum than artemisinin (IC50 = 6 nM). Eight compounds (12, 32, 33, 44, 59, 62, 64, and 66) exhibited equal or better antileishmanial activities than 1 (IC50 = 1.8 mu M). Several congeners were more active than I in vivo, curing at least 2/4 infected animals in the acute mouse model of trypanosomiasis. The diimidazoline 66 was the most promising compound in the series, showing excellent in vitro activities and high selectivities against T. b. rhodesiense, P. falciparum, and L. donovani combined with high antitrypanosomal efficacy in vivo.

  DOI：

  10.1021/jm801547t

文献信息

• Analogs of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia
  作者：Richard R. Tidwell、Susan Kilgore Jones、J. Dieter Geratz、Kwasi A. Ohemeng、Michael Cory、James Edwin Hall

  DOI：10.1021/jm00166a026

  日期：1990.4

  A series of 33 analogues of the anti-Pneumocystis carinii drug 1,5-bis(4-amidinophenoxy)pentane (pentamidine) was synthesized for screening against a rat model of P. carinii pneumonia (PCP). Twenty-five of the compounds showed efficacy against PCP when compared to a saline-treated control group. Two compounds, 1,4-bis(4-amidinophenoxy)butane (butamidine, 6) and 1,3-bis(4-amidino-2-methoxyphenoxy)propane (DAMP, 16), were statistically more effective than the parent drug in treating PCP in the rat model of infection. In addition to their activity against PCP, the compounds were also evaluated for antitrypsin activity, ability to inhibit thymidylate synthetase, affinity for DNA, and toxicity. No correlation was observed between the tested molecular interactions of the diamidines and their effectiveness against PCP.
• TIDWELL, RICHARD R.;JONES, SUSAN KILGORE;GERATZ, J. DIETER;OHEMENG, KWASI+, J. MED. CHEM., 33,(1990) N, C. 1252-1257
  作者：TIDWELL, RICHARD R.、JONES, SUSAN KILGORE、GERATZ, J. DIETER、OHEMENG, KWASI+

  DOI：——

  日期：——
• Structure−Activity Study of Pentamidine Analogues as Antiprotozoal Agents
  作者：Svetlana M. Bakunova、Stanislav A. Bakunov、Donald A. Patrick、E. V. K. Suresh Kumar、Kwasi A. Ohemeng、Arlene S. Bridges、Tanja Wenzler、Todd Barszcz、Susan Kilgore Jones、Karl A. Werbovetz、Reto Brun、Richard R. Tidwell

  DOI：10.1021/jm801547t

  日期：2009.4.9

  Diamidine 1 (pentamidine) and 65 analogues (2-66) have been tested for in vitro antiprotozoal activities against Trypanosoma brucei rhodesiense, Plasmodium. falciparum, and Leishmania donovani, and for cytotoxicity against mammalian cells. Dications 32, 64, and 66 exhibited antitrypanosomal potencies equal or greater than melarsoprol (IC50 = 4 nM). Nine congeners (2-4, 12, 27, 30, and 64-66) were more active against P. falciparum than artemisinin (IC50 = 6 nM). Eight compounds (12, 32, 33, 44, 59, 62, 64, and 66) exhibited equal or better antileishmanial activities than 1 (IC50 = 1.8 mu M). Several congeners were more active than I in vivo, curing at least 2/4 infected animals in the acute mouse model of trypanosomiasis. The diimidazoline 66 was the most promising compound in the series, showing excellent in vitro activities and high selectivities against T. b. rhodesiense, P. falciparum, and L. donovani combined with high antitrypanosomal efficacy in vivo.