adamantane-2-spiro-3'-5',5'-bis[4'-(aminomethyl)phenyl]-1',2',4'-trioxolane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: adamantane-2-spiro-3'-5',5'-bis[4'-(aminomethyl)phenyl]-1',2',4'-trioxolane
• 英文别名: [4-[3-[4-(Aminomethyl)phenyl]spiro[1,2,4-trioxolane-5,2'-adamantane]-3-yl]phenyl]methanamine
• 化学式: C₂₅H₃₀N₂O₃
• 分子量: 406.525
• InChiKey: DKCHKZZZHSCRRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  79.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,4'-二甲基二苯甲酮 在 potassium permanganate 、 锂硼氢 、 偶氮二甲酸二异丙酯 、 硫酸 、 三乙基硼氢化锂 、 臭氧 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 甲苯 、 正戊烷 为溶剂， 反应 72.0h， 生成 adamantane-2-spiro-3'-5',5'-bis[4'-(aminomethyl)phenyl]-1',2',4'-trioxolane
  参考文献：
  名称：

  Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes

  摘要：

  Based on the structures of several lipophilic trioxolane antimalarial prototypes, we set out to determine which functional groups were associated with good antimalarial profiles and identify more polar (lower LogP/LogD) lead compounds with good physicochemical properties. More lipophilic trioxolanes tended to have better oral activities than their more polar counterparts. Trioxolanes with a wide range of neutral and basic, but not acidic, functional groups had good antimalarial profiles. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.041

文献信息

• US7371778B2
  申请人：——

  公开号：US7371778B2

  公开（公告）日：2008-05-13
• Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes
  作者：Y DONG、Y TANG、J CHOLLET、H MATILE、S WITTLIN、S CHARMAN、W CHARMAN、J TOMAS、C SCHEURER、C SNYDER

  DOI：10.1016/j.bmc.2006.05.041

  日期：2006.9.15

  Based on the structures of several lipophilic trioxolane antimalarial prototypes, we set out to determine which functional groups were associated with good antimalarial profiles and identify more polar (lower LogP/LogD) lead compounds with good physicochemical properties. More lipophilic trioxolanes tended to have better oral activities than their more polar counterparts. Trioxolanes with a wide range of neutral and basic, but not acidic, functional groups had good antimalarial profiles. (c) 2006 Elsevier Ltd. All rights reserved.