thioacetic acid S-(3-methoxybenzyl) ester | 873463-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: thioacetic acid S-(3-methoxybenzyl) ester
• 英文别名: S-[(3-methoxyphenyl)methyl] ethanethioate
• CAS: 873463-99-1
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: NRQZBRZHIHAXFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-(3-methoxybenzyl) ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 5a-(3-cyanobenzylsulfanyl)dihydrobicyclomycin
  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
• 作为产物：
  描述：

  3-甲氧基溴苄 、 potassium thioacetate 以 丙酮 为溶剂， 以81%的产率得到thioacetic acid S-(3-methoxybenzyl) ester
  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