3-(trans-4-tert-butyl-cyclohexylmethyl)-2-methoxy[1,4]naphthoquinone | 735312-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(trans-4-tert-butyl-cyclohexylmethyl)-2-methoxy[1,4]naphthoquinone
• CAS: 735312-06-8
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: RFHDRSHQIJZCTI-SHTZXODSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(trans-4-tert-butyl-cyclohexylmethyl)-2-methoxy[1,4]naphthoquinone 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 生成 (Z)-3-(trans-4-tert-butyl-cyclohexylmethyl)-2-methoxy[1,4]naphthoquinone-1-oxime 、 (E)-3-(trans-4-tert-butyl-cyclohexylmethyl)-2-methoxy[1,4]naphthoquinone-1-oxime
  参考文献：
  名称：

  Synthesis and antileishmanial activity of novel buparvaquone oxime derivatives

  摘要：

  Novel oxime derivatives (2, 3 and 5) of buparvaquone (1) and O-methyl-buparvaquone (4) were synthesized and their in vitro activities against Leishmania donovani, the causative agent of visceral leishmaniasis (VL), were determined. Buparvaquone-oxime (2) was also studied as a bioreversible prodrug structure of buparvaquone (1). Buparvaquone-oxime (2) released buparvaquone (1) in vitro when it was incubated with induced rat liver microsomes, which suggests that the oxime-structure is a useful prodrug template for developing novel prodrugs of buparvaquone and other hydroxynaphthoquinones. Moreover, the formation of NO2-, formed via oxidation of NO, was confirmed during the bioconversion. The release of NO from buparvaquone-oxime (2) may provide an additional therapeutic effect in the treatment of leishmaniasis. Buparvaquone-oxime (2) and buparvaquone-O-methyloxime (3) demonstrated moderate activity against amastigotes of the Leishmania species that causes VL. However, the studied oximes (2, 3) most probably did not release buparvaquone (1) and NO during the present in vitro experiment. Further in vivo studies are needed to verify the biological activity of buparvaquone-oximes in the treatment of leishmaniasis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.032
• 作为产物：
  描述：

  3-(trans-4-tert-butyl-cyclohexylmethyl)-2-hydroxy[1,4]naphthoquinone-1-oxime 在 magnesium chloride phosphate buffer 、 liver microsomes from rats treated with dexamethasone 、 potassium carbonate 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 3-(trans-4-tert-butyl-cyclohexylmethyl)-2-methoxy[1,4]naphthoquinone
  参考文献：
  名称：

  Synthesis and antileishmanial activity of novel buparvaquone oxime derivatives

  摘要：

  Novel oxime derivatives (2, 3 and 5) of buparvaquone (1) and O-methyl-buparvaquone (4) were synthesized and their in vitro activities against Leishmania donovani, the causative agent of visceral leishmaniasis (VL), were determined. Buparvaquone-oxime (2) was also studied as a bioreversible prodrug structure of buparvaquone (1). Buparvaquone-oxime (2) released buparvaquone (1) in vitro when it was incubated with induced rat liver microsomes, which suggests that the oxime-structure is a useful prodrug template for developing novel prodrugs of buparvaquone and other hydroxynaphthoquinones. Moreover, the formation of NO2-, formed via oxidation of NO, was confirmed during the bioconversion. The release of NO from buparvaquone-oxime (2) may provide an additional therapeutic effect in the treatment of leishmaniasis. Buparvaquone-oxime (2) and buparvaquone-O-methyloxime (3) demonstrated moderate activity against amastigotes of the Leishmania species that causes VL. However, the studied oximes (2, 3) most probably did not release buparvaquone (1) and NO during the present in vitro experiment. Further in vivo studies are needed to verify the biological activity of buparvaquone-oximes in the treatment of leishmaniasis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.032