6-acetyl-5-butoxybenzo[d][1,3]oxathiole | 1262430-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Benzoxathioles
• 英文名称: 6-acetyl-5-butoxybenzo[d][1,3]oxathiole
• 英文别名: 1-(5-Butoxy-1,3-benzoxathiol-6-yl)ethanone
• CAS: 1262430-62-5
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: CVBCNJMZPOVNQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氟-4-甲氧基苯甲醛 、 6-acetyl-5-butoxybenzo[d][1,3]oxathiole 以67%的产率得到(E)-1-(5-butoxybenzo[d][1,3]oxathiol-6-yl)-3-(3-fluoro-4-methoxyphenyl)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 6-acetyl-5-butoxybenzo[d][1,3]oxathiole
  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

文献信息

• [EN] NOVEL CHALCONE DERIVATIVES WITH CYTOTOXIC ACTIVITY<br/>[FR] NOUVEAUX DÉRIVÉS DE CHALCONE PRÉSENTANT UNE ACTIVITÉ CYTOTOXIQUE
  申请人：ADAMED SP ZOO

  公开号：WO2011009826A3

  公开（公告）日：2011-06-09
• Structural Factors Affecting Cytotoxic Activity of (<i>E</i>)-1-(Benzo[<i>d </i>][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives
  作者：Marek T. Konieczny、Anita Bułakowska、Justyna Polak、Danuta Pirska、Wojciech Konieczny、Patrycja Gryń、Andrzej Skladanowski、Michał Sabisz、Krzysztof Lemke、Anna Pieczykolan、Marlena Gałązka、Katarzyna Wiciejowska、Joanna Wietrzyk

  DOI：10.1111/cbdd.12296

  日期：2014.7

  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.