dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1"-cyclohexane]-7-ol | 1029907-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1"-cyclohexane]-7-ol
• CAS: 1029907-33-2
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: JUQMZAOUCZTFBL-UHFFFAOYSA-N

物化性质

• 沸点：
  408.7±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1"-cyclohexane]-7-ol 、 丹酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以29%的产率得到dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1''-cyclohexane]-7-yl 5-(dimethylamino)naphthalene-1-sulfonate
  参考文献：
  名称：

  [EN] CYCLIC PEROXIDES AS PRODRUGS FOR SELECTIVE DELIVERY OF AGENTS
  [FR] PEROXYDES CYCLIQUES UTILISÉS EN TANT QUE PROMÉDICAMENTS POUR L'ADMINISTRATION SÉLECTIVE D'AGENTS

  摘要：

  本文披露了前药组合物及其用于治疗和检测疾病的方法。具体地，本文披露了一种具有螺合1,2,4-三噁烷和哌啶环的化合物的公式(I)，即1,2,4-三氧杂-8-氮杂螺[4.5]癸烷。还披露了含有该化合物和药用载体的药物组合物。

  公开号：

  WO2015123595A1

文献信息

• SPIRO AND DISPIRO 1,2,4-TRIOXOLANE ANTIMALARIALS
  申请人：VENNERSTROM JONATHAN L.

  公开号：US20080125441A1

  公开（公告）日：2008-05-29

  A means and method for treating malaria, schistosomiasis, and cancer using a Spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  本发明涉及使用Spiro或dispiro 1,2,4-三噁烷治疗疟疾、血吸虫病和癌症的方法和手段。首选的1,2,4-三噁烷包括一个spiroadamantane基团位于三噁烷基团的一侧，而spirocyclohexyl位于三噁烷基团的另一侧，其中spirocyclohexyl环在4位处被取代。与青蒿素半合成衍生物相比，本发明化合物结构简单，易于合成，无毒，并且对疟原虫具有强效作用。
• Cyclic peroxides as prodrugs for selective delivery of agents
  申请人：The Regents of the University of California

  公开号：US10287312B2

  公开（公告）日：2019-05-14

  Disclosed herein, inter alia, are prodrug compositions and methods of using the same for treatment and detection of disease. Specifically, disclosed herein is a compound of formula (I) having spiro-fused 1,2,4-trioxolane and piperidine rings, namely, 1,2,4-trioxa-8-azaspiro[4.5]decane. Also disclosed is a pharmaceutical composition containing the compound and a pharmaceutically acceptable carrier.

  本文特别公开了原药组合物以及使用原药组合物治疗和检测疾病的方法。具体地说，本文公开了一种具有螺融合 1，2，4-三氧环和哌啶环的式 (I) 化合物，即 1，2，4-三氧杂-8-氮杂螺[4.5]癸烷。还公开了一种药物组合物，其中含有该化合物和一种药学上可接受的载体。
• Investigating the Antimalarial Action of 1,2,4-Trioxolanes with Fluorescent Chemical Probes
  作者：Carmony L. Hartwig、Erica M.W. Lauterwasser、Sumit S. Mahajan、Jonathan M. Hoke、Roland A. Cooper、Adam R. Renslo

  DOI：10.1021/jm2012003

  日期：2011.12.8

  The 1,2,4-trioxolanes are a new class of synthetic peroxidic antimalarials currently in human clinical trials. The well-known reactivity of the 1,2,4-trioxolane ring toward inorganic ferrous iron and ferrous iron heme is proposed to play a role in the antimalarial action of this class of compounds. We have designed structurally relevant fluorescent chemical probes to study the subcellular localization of 1,2,4-trioxolanes in cultured Plasmodium falciparum parasites. Microscopy experiments revealed that a probe fluorescently labeled on the adamantane ring accumulated specifically in digestive vacuole-associated neutral lipid bodies within the parasite while an isosteric, but nonperoxidic, congener did not. Probes fluorescently labeled on the cyclohexane ring showed no distinct localization pattern. In their subcellular localization and peroxidative effects, 1,2,4-trioxolane probes behave much like artemisinin-based probes studied previously. Our results are consistent with a role for adamantane-derived carbon-centered radicals in the antimalarial action of 1,2,4-trioxolanes, as hypothesized previously on the basis of chemical reactivity studies.
• CYCLIC PEROXIDES AS PRODRUGS FOR SELECTIVE DELIVERY OF AGENTS
  申请人：The Regents of the University of California

  公开号：EP3104857A1

  公开（公告）日：2016-12-21
• [EN] SPIRO AND DISPIRO 1,2,4-TRIOXOLANE ANTIMALARIALS<br/>[FR] ANTIPALUDIQUES SPIRO- ET DISPIRO-1,2,4-TRIOXOLANE
  申请人：MEDICINES MALARIA VENTURE MMV

  公开号：WO2009091433A2

  公开（公告）日：2009-07-23

  A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.