N-(6-chloro-9-oxo-9H-xanthen-4-yl)2,3,4,5,6-pentafluorobenzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(6-chloro-9-oxo-9H-xanthen-4-yl)2,3,4,5,6-pentafluorobenzenesulfonamide
• 化学式: C₁₉H₇ClF₅NO₄S
• 分子量: 475.78
• InChiKey: IZPOENQENPVUOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.38
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-chloro-5-nitro-9H-xanthen-9-one 在 盐酸 、 溶剂黄146 、 三乙胺 、 tin(ll) chloride 作用下， 以 氯仿 、 水 为溶剂， 生成 N-(6-chloro-9-oxo-9H-xanthen-4-yl)2,3,4,5,6-pentafluorobenzenesulfonamide
  参考文献：
  名称：

  Synthesis and evaluation of antiproliferative activity of substituted N-(9-oxo-9H-xanthen-4-yl)benzenesulfonamides

  摘要：

  Several novel N-(9-oxo-9H-xanthen-4-yl)benzenesulfonamide derivatives were prepared as potential antiproliferative agents. The in vitro antiproliferative activity of the synthesized compounds was investigated against a panel of tumor cell lines including breast cancer cell lines (MDA-MB-231, T-47D) and neuroblastoma cell line (SK-N-MC) using MTT colorimetric assay. Etoposide, a well-known anticancer drug, was used as a positive standard drug. Among synthesized compounds, 4-methoxy-N-(9-oxo-9H-xanthen-4-yl)benzenesulfonamide (5i) showed the highest antiproliferative activity against MDA-MB-231, T-47D, and SK-N-MC cells. Furthermore, pentafluoro derivatives 5a and 6a exhibited higher antiproliferative activity than doxorubicin against human leukemia cell line (CCRF-CEM) and breast adenocarcinoma (MDA-MB-468) cells. Structure-activity relationship studies revealed that xanthone benzenesulfonamide hybrid compounds can be used for the development of new lead anticancer agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.033

文献信息

• Synthesis and evaluation of antiproliferative activity of substituted N-(9-oxo-9H-xanthen-4-yl)benzenesulfonamides
  作者：Somayeh Motavallizadeh、Asal Fallah-Tafti、Saeedeh Maleki、Amir Nasrolahi Shirazi、Mahboobeh Pordeli、Maliheh Safavi、Sussan Kabudanian Ardestani、Shaaban Asd、Rakesh Tiwari、Donghoon Oh、Abbas Shafiee、Alireza Foroumadi、Keykavous Parang、Tahmineh Akbarzadeh

  DOI：10.1016/j.tetlet.2013.11.033

  日期：2014.1

  Several novel N-(9-oxo-9H-xanthen-4-yl)benzenesulfonamide derivatives were prepared as potential antiproliferative agents. The in vitro antiproliferative activity of the synthesized compounds was investigated against a panel of tumor cell lines including breast cancer cell lines (MDA-MB-231, T-47D) and neuroblastoma cell line (SK-N-MC) using MTT colorimetric assay. Etoposide, a well-known anticancer drug, was used as a positive standard drug. Among synthesized compounds, 4-methoxy-N-(9-oxo-9H-xanthen-4-yl)benzenesulfonamide (5i) showed the highest antiproliferative activity against MDA-MB-231, T-47D, and SK-N-MC cells. Furthermore, pentafluoro derivatives 5a and 6a exhibited higher antiproliferative activity than doxorubicin against human leukemia cell line (CCRF-CEM) and breast adenocarcinoma (MDA-MB-468) cells. Structure-activity relationship studies revealed that xanthone benzenesulfonamide hybrid compounds can be used for the development of new lead anticancer agents. (C) 2013 Elsevier Ltd. All rights reserved.