10-benzoyl-6,8,9-trichloro-5-imino-3,5-dihydro-2H-oxazolo[3,2-b]isoquinoline-7-carbonitrile | 1192010-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 10-benzoyl-6,8,9-trichloro-5-imino-3,5-dihydro-2H-oxazolo[3,2-b]isoquinoline-7-carbonitrile
• 英文别名: 10-Benzoyl-6,8,9-trichloro-5-imino-2,3-dihydro-[1,3]oxazolo[3,2-b]isoquinoline-7-carbonitrile
• CAS: 1192010-71-1
• 化学式: C₁₉H₁₀Cl₃N₃O₂
• 分子量: 418.666
• InChiKey: YVPCNQNJTVRLJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4,5-trichloro-6-(1-(oxazolidin-2-ylidene)-2-oxo-2-phenylethyl)isophthalonitrile 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 10-benzoyl-6,8,9-trichloro-5-imino-3,5-dihydro-2H-oxazolo[3,2-b]isoquinoline-7-carbonitrile
  参考文献：
  名称：

  Facile Route to 1,3-Diazaheterocycle-Fused [1,2b]Isoquinolin-1(2H)-one Derivatives via Substitution-Cyclization Reactions

  摘要：

  The substitution-cyclization reaction of heterocyclic ketene aminals with polyhalo isophthalonitrile in the presence of t-BuOK to form 1,3-diazaheterocycle fused [1,2-b]isoquinolin-1(2H)-imines, followed by hydrolysis with 1N HCl, provides a concise and efficient route for the synthesis of highly functional polyhalo 1,3-diazaheterocycle fused [1,2-b]isoquinolin-1(2H)-ones.

  DOI：

  10.1021/cc900121c

文献信息

• Biological evaluation of polyhalo 1,3-diazaheterocycle fused isoquinolin-1(2H)-imine derivatives
  作者：Chao Huang、Sheng-Jiao Yan、Xiang-Hui Zeng、Xiao-Yang Dai、Yin Zhang、Chen Qing、Jun Lin

  DOI：10.1016/j.ejmech.2011.01.036

  日期：2011.4

  A series of polyhalo 1,3-diazaheterocycle fused isoquinolin-1(2H)-imines were evaluated in vitro against human tumour cell lines including A431, K562, HL60, HepG2 and Skov-3. As a result, some of the target compounds such as 5b, 5c, 5i, 5o, 6c, 6h and 7f showed stronger cytotoxicity against K562, H562 and Skov-3 cells in comparison with cisplatin, and the others displayed moderate cytotoxicity to A431 and HepG2. Biological investigations using the representative compounds 5c, 6c and 6h were also performed in mice bearing S(180) and H(22) tumours. The results indicated that these three compounds inhibit S(180) and H22 growth. In addition, compounds 6c and 6h have very low acute toxicities. The preliminary analysis of structure-activity relationships is also discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Facile Route to 1,3-Diazaheterocycle-Fused [1,2<i>b</i>]Isoquinolin-1(2<i>H</i>)-one Derivatives via Substitution-Cyclization Reactions
  作者：Shengjiao Yan、Chao Huang、Cunxiang Su、Yongfen Ni、Jun Lin

  DOI：10.1021/cc900121c

  日期：2010.1.11

  The substitution-cyclization reaction of heterocyclic ketene aminals with polyhalo isophthalonitrile in the presence of t-BuOK to form 1,3-diazaheterocycle fused [1,2-b]isoquinolin-1(2H)-imines, followed by hydrolysis with 1N HCl, provides a concise and efficient route for the synthesis of highly functional polyhalo 1,3-diazaheterocycle fused [1,2-b]isoquinolin-1(2H)-ones.