7-methoxy-6-octyl-3,4-dihydro-1,1-dioxo-2H-1,4-benzothiazine-5,8-dione | 1217023-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 7-methoxy-6-octyl-3,4-dihydro-1,1-dioxo-2H-1,4-benzothiazine-5,8-dione
• 英文别名: 7-methoxy-6-octyl-1,1-dioxo-3,4-dihydro-2H-1lambda6,4-benzothiazine-5,8-dione；7-methoxy-6-octyl-1,1-dioxo-3,4-dihydro-2H-1λ6,4-benzothiazine-5,8-dione
• CAS: 1217023-25-0
• 化学式: C₁₇H₂₅NO₅S
• 分子量: 355.455
• InChiKey: YASJXOUOGUCIBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  亚牛磺酸 、 2-octyl-3-methoxycyclohexa-2,5-diene-1,4-dione 以 乙醇 、 水 、 乙腈 为溶剂， 生成 7-methoxy-6-octyl-3,4-dihydro-1,1-dioxo-2H-1,4-benzothiazine-5,8-dione 、 6-methoxy-7-octyl-3,4-dihydro-1,1-dioxo-2H-1,4-benzothiazine-5,8-dione
  参考文献：
  名称：

  Synthesis of structurally simplified analogues of aplidinone A, a pro-apoptotic marine thiazinoquinone

  摘要：

  The synthesis of analogues of aplidinone A (7), a prenylated quinone isolated from the Mediterranean ascidian Aplidium conicum, has been performed. This work not only allowed confirming the structural assignment of aplidinone A, previously made with the support of GIAO shielding calculations, but, above all, made a series of structurally related quinone derivatives (compounds 8-13 and the natural metabolite) available for a screening in vitro for cytotoxic and pro-apoptotic activity and for SAR studies. The study evidenced one of the synthetic analogues (11) as a potent cytotoxic and pro-apoptotic agent against several tumor cell lines which also inhibits the TNF alpha-induced NF-kappa B activation in a human leukemia T cell line. This exemplifies the potential of a natural product to qualify as lead structure for medicinal chemistry campaigns, affording simplified analogues with better bioactivity and easier to synthesize. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.063

文献信息

• Synthesis of structurally simplified analogues of aplidinone A, a pro-apoptotic marine thiazinoquinone
  作者：Anna Aiello、Ernesto Fattorusso、Paolo Luciano、Marialuisa Menna、Marco A. Calzado、Eduardo Muñoz、Francesco Bonadies、Marcella Guiso、Maria Filomena Sanasi、Gianfranco Cocco、Rosario Nicoletti

  DOI：10.1016/j.bmc.2009.11.063

  日期：2010.1

  The synthesis of analogues of aplidinone A (7), a prenylated quinone isolated from the Mediterranean ascidian Aplidium conicum, has been performed. This work not only allowed confirming the structural assignment of aplidinone A, previously made with the support of GIAO shielding calculations, but, above all, made a series of structurally related quinone derivatives (compounds 8-13 and the natural metabolite) available for a screening in vitro for cytotoxic and pro-apoptotic activity and for SAR studies. The study evidenced one of the synthetic analogues (11) as a potent cytotoxic and pro-apoptotic agent against several tumor cell lines which also inhibits the TNF alpha-induced NF-kappa B activation in a human leukemia T cell line. This exemplifies the potential of a natural product to qualify as lead structure for medicinal chemistry campaigns, affording simplified analogues with better bioactivity and easier to synthesize. (C) 2009 Elsevier Ltd. All rights reserved.