6-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one | 947245-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one
• 英文别名: 6-Acetyl-5-hydroxy-1,3-benzoxathiol-2-one
• CAS: 947245-15-0
• 化学式: C₉H₆O₄S
• 分子量: 210.21
• InChiKey: IZKWJUMXPUJLMA-UHFFFAOYSA-N

物化性质

• 熔点：
  150-154 °C
• 沸点：
  411.8±55.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
  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：

  5-acetoxy-benzo[1,3]oxathiol-2-one 在 三氯化铝 作用下， 反应 4.0h， 以8.8 g的产率得到6-acetyl-5-hydroxybenzo[1,3]oxathiol-2-one
  参考文献：
  名称：

  Synthesis of Isomeric, Oxathiolone Fused Chalcones, and Comparison of Their Activity toward Various Microorganisms and Human Cancer Cells Line

  摘要：

  在酸性条件下，通过将适当的乙酰苯并[1,3]氧硫杂环戊-2-酮与苯甲醛缩合，制备了同分异构的氧硫杂环戊酮融合查耳酮。利用 HeLa 细胞对合成的化合物进行了细胞毒性活性筛选，并对黄体微球菌、金黄色葡萄球菌、伤寒沙门氏菌、大肠杆菌、普通变形杆菌进行了抗菌活性筛选，对白色念珠菌进行了抗真菌活性筛选，对结核分枝杆菌 H37Rv 和堪萨斯分枝杆菌菌株进行了抗结核活性筛选。

  DOI：

  10.1248/cpb.55.817

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
• Synthesis of oxathiolone fused chalcones bearing O-aminoalkyl side chain. Comparison of stability of isomeric benzoxathiolones under alkylation reaction conditions
  作者：M KONIECZNY、W KONIECZNY、D PIRSKA、A BULAKOWSKA、M SABISZ、A SKLADANOWSKI、R WAKIEC、E AUGUSTYNOWICZKOPEC、Z ZWOLSKA

  DOI：10.1016/s0385-5414(07)81197-x

  日期：2007.12.1

  Isomeric, oxathiolone fused chalcones bearing 0-aminoalkyl side chain were synthesized by condensation of suitable benzoxathiolones with substituted benzaldehydes. The starting benzoxathiolones were prepared by O-alkylation of corresponding phenols with aminoalkyl chlorides, however, the reaction was often complicated by amino group catalyzed opening of the oxathiolone ring. The obtained chalcones were screened for antimicrobial and cytotoxic activity.