6,6-dimethyl-2-(2,4,6-trichlorophenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one | 1391041-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-dimethyl-2-(2,4,6-trichlorophenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one
• 英文别名: 6,6-Dimethyl-2-(2,4,6-trichlorophenyl)imino-5,7-dihydro-1,3-benzoxathiol-4-one
• CAS: 1391041-94-3
• 化学式: C₁₅H₁₂Cl₃NO₂S
• 分子量: 376.691
• InChiKey: WFEKYWHYYBMWBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine 、 2,4,6-三氯异硫氰酸苯酯 在 rhodium(II)acetate 作用下， 以 苯 为溶剂， 生成 6,6-dimethyl-2-(2,4,6-trichlorophenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one
  参考文献：
  名称：

  Study on anti-proliferative effect of benzoxathiole derivatives through inactivation of NF-κB in human cancer cells

  摘要：

  To investigate the anti-proliferative effect of a newly discovered NF-kB inhibitor, 6,6-dimethyl-2-(phenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one (1a), a series of its analogs (1b-n) were prepared and evaluated for their NF-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Slight variation of hydrophobicity by replacement of dimethyl group of 1a at 6-position with bulky isopropyl group and introduction of para-fluoro substitution on 2-phenyl group showed good NF-kappa B inhibitory activity and anti-proliferative activity. However, excessive increase in hydrophobicity with 2,4,6-trichloro substituents on phenyl group resulted in the loss of both the activities. From the SAR results, 2-phenylimino-6,7-dihydrobenzo[d][1,3] oxathiol-4(5H)-one was identified as the lead scaffold for investigating new anticancer agent through inactivation of NF-kappa B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.001

文献信息

• Study on anti-proliferative effect of benzoxathiole derivatives through inactivation of NF-κB in human cancer cells
  作者：Eeda Venkateswararao、Hoang Le Tuan Anh、Vinay K. Sharma、Ki-Cheul Lee、Niti Sharma、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2012.06.001

  日期：2012.7

  To investigate the anti-proliferative effect of a newly discovered NF-kB inhibitor, 6,6-dimethyl-2-(phenylimino)-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-one (1a), a series of its analogs (1b-n) were prepared and evaluated for their NF-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Slight variation of hydrophobicity by replacement of dimethyl group of 1a at 6-position with bulky isopropyl group and introduction of para-fluoro substitution on 2-phenyl group showed good NF-kappa B inhibitory activity and anti-proliferative activity. However, excessive increase in hydrophobicity with 2,4,6-trichloro substituents on phenyl group resulted in the loss of both the activities. From the SAR results, 2-phenylimino-6,7-dihydrobenzo[d][1,3] oxathiol-4(5H)-one was identified as the lead scaffold for investigating new anticancer agent through inactivation of NF-kappa B. (C) 2012 Elsevier Ltd. All rights reserved.