1,5-bis[4-(1H-tetrazol-5-yl)phenoxy]pentane | 1135356-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-bis[4-(1H-tetrazol-5-yl)phenoxy]pentane
• 英文别名: 1,5-bis[(1H-tetrazol-5-yl)benzene-4-oxy]pentane；5-[4-[5-[4-(2H-tetrazol-5-yl)phenoxy]pentoxy]phenyl]-2H-tetrazole
• CAS: 1135356-93-2
• 化学式: C₁₉H₂₀N₈O₂
• 分子量: 392.42
• InChiKey: UABIQSUBJCGZHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,5-二(4-氰基苯氧基)戊烷 在 sodium azide 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到1,5-bis[4-(1H-tetrazol-5-yl)phenoxy]pentane
  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

• FSO₂N₃-Enabled Synthesis of Tetrazoles from Amidines and Guanidines
  作者：Tianyu Wang、Long Xu、Jiajia Dong

  DOI：10.1021/acs.orglett.3c02470

  日期：2023.8.25

  and orthogonally. As the follow-up studies of the diazo transfer reaction using FSO2N3, we discover that amidines and guanidines are rapidly transformed into tetrazole derivatives when reacting with FSO2N3 under an aqueous environment, which is unprecedented for tetrazole synthesis.

  在此，我们报道了在温和条件下通过 FSO 2 N 3实现四唑的简便合成。FSO 2 N 3已被证明是最强大的重氮化试剂，可将数千种伯胺快速且正交地转化为叠氮化物。作为FSO 2 N 3重氮转移反应的后续研究，我们发现脒和胍在水相环境下与FSO 2 N 3反应时迅速转化为四唑衍生物，这对于四唑合成来说是前所未有的。
• 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.