bicyclomycin

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bicyclomycin
• 英文别名: (1R,6S)-6-hydroxy-5-methylidene-1-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-2-oxa-7,9-diazabicyclo[4.2.2]decane-8,10-dione
• 化学式: C₁₂H₁₈N₂O₇
• 分子量: 302.284
• InChiKey: WOUDXEYYJPOSNE-ZZKLTDFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bicyclomycin 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5a-(3-chlorobenzylsulfanyl)dihydrobicyclomycin 2',3'-acetonide
  参考文献：
  名称：

  Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties

  摘要：

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.075

文献信息

• Process for producing biocozamycin benzoate
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05525722A1

  公开（公告）日：1996-06-11

  A process for producing bicozamycin benzoate is provided which comprises reacting bicozamycin with benzoic anhydride in the presence of 4-dimethylaminopyridine. The process provided for producing bicozamycin benzoate gives improved yields as compared with the prior art process.

  提供了一种生产双苯甲酸双可唑霉素的方法，包括在4-二甲基氨基吡啶存在下，将双可唑霉素与苯甲酸酐反应。与先前工艺相比，该方法提供的生产双苯甲酸双可唑霉素的方法能够得到更高的产量。
• Fluorine-substituted dihydrobicyclomycins: Synthesis and biochemical and biological properties
  作者：Boon-Saeng Park、William Widger、Harold Kohn

  DOI：10.1016/j.bmc.2005.07.075

  日期：2006.1

  Many studies show that selective introduction of fluorine within pharmacological agents leads to improved activities. In this study, we determine the effects of aryl fluorine substitution in 5a-(benzylsulfanyl)-dihydrobicyclomycin (3) on the in vitro inhibition of Escherichia coli rho-dependent ATPase activity. Compound 3 is an analog of bicyclomycin (1), which is the only known selective inhibitor of rho, and I and 3 have comparable in vitro inhibitory activities. We demonstrate that aryl fluorine substitution of 3 leads to increase in inhibitory activity but that the beneficial effects due to fluorine were dependent upon the site and number of fluorine substituents. The bioactivitics are rationalized in terms of the bond moment created by the aryl fluoride bond within the 5a-aryl dihydrobicyclomycin-rho-binding pocket. Use of this hypothesis led to file design of dihydrobicyclomycin derivatives with superior in vitro rho inhibitory activities. (c) 2005 Elsevier Ltd. All rights reserved.