tert-butyl (3-((6-acetylbenzo[d][1,3]oxathiol-5-yl)oxy)propyl)carbamate | 1644568-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Benzoxathioles
• 英文名称: tert-butyl (3-((6-acetylbenzo[d][1,3]oxathiol-5-yl)oxy)propyl)carbamate
• CAS: 1644568-77-3
• 化学式: C₁₇H₂₃NO₅S
• 分子量: 353.439
• InChiKey: LYTRGMFDGFBWIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  73.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-氟-4-甲氧基苯甲醛 、 tert-butyl (3-((6-acetylbenzo[d][1,3]oxathiol-5-yl)oxy)propyl)carbamate 以49%的产率得到(E)-3-(3-fluoro-4-methoxyphenyl)-1-{5-[3-(1-tert-butoxycarbonylamino)propoxy]benzo[d][1,3]oxathiol-6-yl}prop-2-en-1-one
  参考文献：
  名称：

  Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives

  摘要：

  Derivatives of (E)‐1‐(5‐alkoxybenzo[d][1,3]oxathiol‐6‐yl)‐3‐phenylprop‐2‐en‐1‐one demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects of (i) the heterocyclic ring, (ii) the alkoxy group at position 5 of the benzoxathiole ring, and (iii) the substituents in the phenyl ring B. Replacement of the sulfur atom by oxygen does not influence the activity. None of the listed structural fragments alone assured high cytotoxic activity.

  DOI：

  10.1111/cbdd.12296
• 作为产物：
  描述：

  6-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one 在 碳酸氢钠 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 tert-butyl (3-((6-acetylbenzo[d][1,3]oxathiol-5-yl)oxy)propyl)carbamate
  参考文献：
  名称：

  Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives

  摘要：

  Derivatives of (E)‐1‐(5‐alkoxybenzo[d][1,3]oxathiol‐6‐yl)‐3‐phenylprop‐2‐en‐1‐one demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects of (i) the heterocyclic ring, (ii) the alkoxy group at position 5 of the benzoxathiole ring, and (iii) the substituents in the phenyl ring B. Replacement of the sulfur atom by oxygen does not influence the activity. None of the listed structural fragments alone assured high cytotoxic activity.

  DOI：

  10.1111/cbdd.12296