7-(1-adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane | 1142402-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 7-(1-adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane
• CAS: 1142402-26-3
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: XDSSIDDABXBCPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(1-adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane 、 β-cyclodextrin 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Elucidation of the in vitro and in vivo activities of bridged 1,2,4-trioxolanes, bridged 1,2,4,5-tetraoxanes, tricyclic monoperoxides, silyl peroxides, and hydroxylamine derivatives against Schistosoma mansoni

  摘要：

  Praziquantel is currently the only drug available to treat schistosomiasis. Since drug resistance would be a major barrier for the increasing global attempts to eliminate schistosomiasis as a public health problem, efforts should go hand in hand with the discovery of novel treatment options. Synthetic peroxides might offer a good direction since their antischistosomal activity has been demonstrated in the laboratory. We studied 19 bridged 1,2,4,5-tetraoxanes, 2 tricyclic monoperoxides, 11 bridged 1,2,4-trioxolanes, 12 silyl peroxides, and 4 hydroxylamine derivatives against newly transformed schistosomula (NTS) and adult Schistosoma mansoni in vitro. Schistosomicidal compounds were tested for cytotoxicity followed by in vivo studies of the most promising compounds. Tricyclic monoperoxides, trioxolanes, and tetraoxanes revealed the highest in vitro activity against NTS (IC(50)s 0.4-20.2 mu M) and adult schistosomes (IC(50)s 1.8-22.8 mu M). Tetraoxanes showed higher cytotoxicity than antischistosomal activity. Selected trioxolane and tricyclic monoperoxides were tested in mice harboring an adult S. mansoni infection. The highest activity was observed for two trioxolanes, which showed moderate worm burden reductions (WBR) of 44.3% and 42.9% (p > 0.05). Complexation of the compounds with beta-cyclodextrin with the aim to improve solubility and gastrointestinal absorption did not increase in vivo antischistosomal efficacy. The high in vitro antischistosomal activity of trioxolanes and tricyclic monoperoxides is a promising basis for future investigations, with the focus on improving in vivo efficacy. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.010
• 作为产物：
  描述：

  3-(1-金刚烷)戊烷-2,4-二酮 在 双氧水 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以64%的产率得到7-(1-adamantyl)-1,4-dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Ion exchange resin-catalyzed synthesis of bridged tetraoxanes possessing in vitro cytotoxicity against HeLa cancer cells

  摘要：

  利用现有的酸性离子交换树脂制备了桥接的 1,2,4,5-四氧杂环己烷，尽管在异构条件下可能会发生过氧化物分解，但产量很高。桥接四氧杂环己烷在体外对 HeLa 癌细胞具有很强的细胞毒性，在某些情况下，其毒性高于顺铂、青蒿琥酯和双氢青蒿素。

  DOI：

  10.1007/s10593-020-02722-4

文献信息

• Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application
  作者：Ivan A. Yaremenko、Peter S. Radulov、Yulia Y. Belyakova、Arina A. Demina、Dmitriy I. Fomenkov、Denis V. Barsukov、Irina R. Subbotina、Fabrice Fleury、Alexander O. Terent'ev

  DOI：10.1002/chem.201904555

  日期：2020.4.9

  heterogeneous conditions. Synthesis of peroxides under heterogeneous conditions is a rare process and represents a challenge for this field of chemistry, because peroxides tend to decompose on the surface of a catalyst . A new class of antifungal agents for crop protection, that is, cyclic peroxides: bridged 1,2,4,5-tetraoxanes and bridged ozonides, was discovered. Some ozonides and tetraoxanes exhibit a very

  开发了负载在SiO2上的催化剂H3 + x PMo12-x +6 Mox +5 O40，用于过氧化氢对1,3-和1,5-二酮的过氧化作用，形成桥联的1,2,4,5-四恶烷和在异质条件下，基于分离的产物（分别高达86％和90％），可以高收率连接1,2,4-三氧杂环戊烷（臭氧化物）。在非均相条件下合成过氧化物是一种罕见的方法，并且对该化学领域提出了挑战，因为过氧化物趋于在催化剂表面上分解。发现了用于保护农作物的一类新的抗真菌剂，即环过氧化物：桥连的1,2,4,5-四恶烷和桥连的臭氧化物。一些臭氧化物和四恶烷显示出很高的抗真菌活性，并且优于商业杀真菌剂，例如三唑酮和克雷索辛甲基。
• Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones
  作者：Alexander O. Terent’ev、Dmitry A. Borisov、Vladimir V. Chernyshev、Gennady I. Nikishin

  DOI：10.1021/jo900226b

  日期：2009.5.1

  A facile, experimentally simple, and selective method was developed for the synthesis of bridged 1,2,4,5-tetraoxanes based on the reaction of hydrogen peroxide with beta-diketones catalyzed by strong acids (H2SO4, HClO4, HBF4, or BF3). The yields of the target products vary from 44% to 77%. 1,2,4,5-Tetraoxanes can easily be separated from other reaction products by column chromatography. A high concentration of a strong acid is a key factor determining the selectivity of formation and the yield of 1,2,4,5-tetraoxanes. Unlike many compounds containing the O-O bond. which undergo rearrangements in acidic media, the resulting cyclic peroxides are quite stable under these conditions.
• Ion exchange resin-catalyzed synthesis of bridged tetraoxanes possessing in vitro cytotoxicity against HeLa cancer cells
  作者：Vera A. Vil’、Ivan A. Yaremenko、Dmitri I. Fomenkov、Dmitri O. Levitsky、Fabrice Fleury、Alexander O. Terent’ev

  DOI：10.1007/s10593-020-02722-4

  日期：2020.6

  Bridged 1,2,4,5-tetraoxanes were prepared using available acidic ion exchange resin with high yields despite the possibility of peroxide decomposition under heterogeneous conditions. The bridged tetraoxanes demonstrated high cytotoxicity against HeLa cancer cells in vitro, which in some cases was higher than that of cisplatin, artesunate, and dihydroartemisinin.

  利用现有的酸性离子交换树脂制备了桥接的 1,2,4,5-四氧杂环己烷，尽管在异构条件下可能会发生过氧化物分解，但产量很高。桥接四氧杂环己烷在体外对 HeLa 癌细胞具有很强的细胞毒性，在某些情况下，其毒性高于顺铂、青蒿琥酯和双氢青蒿素。
• Elucidation of the in vitro and in vivo activities of bridged 1,2,4-trioxolanes, bridged 1,2,4,5-tetraoxanes, tricyclic monoperoxides, silyl peroxides, and hydroxylamine derivatives against Schistosoma mansoni
  作者：Noemi Cowan、Ivan A. Yaremenko、Igor B. Krylov、Alexander O. Terent’ev、Jennifer Keiser

  DOI：10.1016/j.bmc.2015.02.010

  日期：2015.8

  Praziquantel is currently the only drug available to treat schistosomiasis. Since drug resistance would be a major barrier for the increasing global attempts to eliminate schistosomiasis as a public health problem, efforts should go hand in hand with the discovery of novel treatment options. Synthetic peroxides might offer a good direction since their antischistosomal activity has been demonstrated in the laboratory. We studied 19 bridged 1,2,4,5-tetraoxanes, 2 tricyclic monoperoxides, 11 bridged 1,2,4-trioxolanes, 12 silyl peroxides, and 4 hydroxylamine derivatives against newly transformed schistosomula (NTS) and adult Schistosoma mansoni in vitro. Schistosomicidal compounds were tested for cytotoxicity followed by in vivo studies of the most promising compounds. Tricyclic monoperoxides, trioxolanes, and tetraoxanes revealed the highest in vitro activity against NTS (IC(50)s 0.4-20.2 mu M) and adult schistosomes (IC(50)s 1.8-22.8 mu M). Tetraoxanes showed higher cytotoxicity than antischistosomal activity. Selected trioxolane and tricyclic monoperoxides were tested in mice harboring an adult S. mansoni infection. The highest activity was observed for two trioxolanes, which showed moderate worm burden reductions (WBR) of 44.3% and 42.9% (p > 0.05). Complexation of the compounds with beta-cyclodextrin with the aim to improve solubility and gastrointestinal absorption did not increase in vivo antischistosomal efficacy. The high in vitro antischistosomal activity of trioxolanes and tricyclic monoperoxides is a promising basis for future investigations, with the focus on improving in vivo efficacy. (C) 2015 Elsevier Ltd. All rights reserved.