6-fluoro-2-adamantanone | 1227734-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-fluoro-2-adamantanone
• 英文别名: 6-Fluoroadamantan-2-one
• CAS: 1227734-62-4
• 化学式: C₁₀H₁₃FO
• 分子量: 168.211
• InChiKey: NFCXYYVBUOXTES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-fluoro-2-adamantanone 、 甲氧基胺盐酸盐 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以94%的产率得到O-methyl-6-fluoro-2-adamantanone oxime
  参考文献：
  名称：

  Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) againstFasciola hepatica

  摘要：

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.

  DOI：

  10.1021/jm100226t
• 作为产物：
  描述：

  6-fluoro-2-adamantanone monoethylene ketal 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以55 mg的产率得到6-fluoro-2-adamantanone
  参考文献：
  名称：

  Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) againstFasciola hepatica

  摘要：

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.

  DOI：

  10.1021/jm100226t

文献信息

• C-HALOGEN BOND FORMATION
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：US20160264512A1

  公开（公告）日：2016-09-15

  Fluorinated compounds are provided. Fluorinated compounds may be prepared by a method of halogenating a carbon containing compound having an sp3 C—H bond.

  提供氟化合物。可以通过卤代含有sp3 C-H键的碳化合物的方法来制备氟化合物。
• Structure−Activity Relationship of an Ozonide Carboxylic Acid (OZ78) against<i>Fasciola hepatica</i>
  作者：Qingjie Zhao、Mireille Vargas、Yuxiang Dong、Lin Zhou、Xiaofang Wang、Kamaraj Sriraghavan、Jennifer Keiser、Jonathan L. Vennerstrom

  DOI：10.1021/jm100226t

  日期：2010.5.27

  In this paper, we describe the SAR of ozonide carboxylic acid OZ78 (1) as the first part of our search for a trematocidal synthetic peroxide drug development candidate. We found that relatively small structural changes to 1 resulted most commonly in loss of activity against Fasciola hepatica in vivo. A spiro-adamantane substructure and acidic functional group (or ester prodrug) were required for activity. Of 26 new compounds administered at single 100 mg/kg oral doses to F. hepatica infected rats, 8 had statistically significant worm burden reductions, 7 were partially curative, and 1 (acylsulfonamide 6) was completely curative and comparable to 1 in flukicidal efficacy. This study also showed that the activity of 1 is peroxide-bond-dependent, suggesting that its flukicidal efficacy depends upon hemoglobin digestion in F. hepatica.