ethyl 5-imino-7-cyano-6,8,9-trifluoro-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carboxylate | 1192010-51-7

• 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: ethyl 5-imino-7-cyano-6,8,9-trifluoro-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carboxylate
• 英文别名: ethyl 7-cyano-6,8,9-trifluoro-5-imino-2,3-dihydro-1H-imidazo[1,2-b]isoquinoline-10-carboxylate
• CAS: 1192010-51-7
• 化学式: C₁₅H₁₁F₃N₄O₂
• 分子量: 336.273
• InChiKey: BMKCZVPGJXZQJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 5-imino-7-cyano-6,8,9-trifluoro-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carboxylate 在 盐酸 、 水 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以86%的产率得到10-ethoxycarbonyl-6,8,9-trifluoro-7-cyano-5-oxo-1,2,3,5-tetrahydroimidazolo[1,2-b]isoquinoline
  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
• 作为产物：
  描述：

  Ethyl 2-(2,4-dicyano-3,5,6-trifluorophenyl)-2-imidazolidin-2-ylideneacetate 在 potassium tert-butylate 作用下， 以 1,4-二氧六环 为溶剂， 以96%的产率得到ethyl 5-imino-7-cyano-6,8,9-trifluoro-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carboxylate
  参考文献：
  名称：

  无溶剂，微波辅助合成多卤代杂环烯酮缩醛作为新型抗癌剂

  摘要：

  在无溶剂条件下合成了一系列多卤代杂环烯酮缩醛（polyhalo-HKA），并在体外针对一组人类肿瘤细胞系进行了评估。三氟-HKA是最具细胞毒性的化合物，其次是二氟-HKA和三氯-HKA。与二氟-HKA相比，三氯-HKA对肿瘤细胞系Skov-3，Hep-2，K562和A431更有效。在多卤代HKAs的2-位上的乙氧羰基具有最高的活性。已发现在间苯二甲腈环上带有三个氟原子的乙氧羰基取代的5o是最有效的衍生物，对五种人类肿瘤细胞系的IC 50值低于3.7μg/ mL，这使其活性比顺铂（DDP）高。

  DOI：

  10.1016/j.bmcl.2009.11.044

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.
• Solvent-free, microwave assisted synthesis of polyhalo heterocyclic ketene aminals as novel anti-cancer agents
  作者：Sheng-Jiao Yan、Chao Huang、Xiang-Hui Zeng、Rong Huang、Jun Lin

  DOI：10.1016/j.bmcl.2009.11.044

  日期：2010.1

  A series of polyhalo heterocyclic ketene aminals (polyhalo-HKAs) were synthesized under solvent-free conditions and evaluated in vitro against a panel of human tumor cell lines. Trifluoro-HKAs were the most cytotoxic compounds, followed by difluoro-HKAs and trichloro-HKAs. Trichloro-HKAs were more potent against the tumor cell lines Skov-3, Hep-2, K562, and A431 than difluoro-HKAs. An ethoxycarbonyl

  在无溶剂条件下合成了一系列多卤代杂环烯酮缩醛（polyhalo-HKA），并在体外针对一组人类肿瘤细胞系进行了评估。三氟-HKA是最具细胞毒性的化合物，其次是二氟-HKA和三氯-HKA。与二氟-HKA相比，三氯-HKA对肿瘤细胞系Skov-3，Hep-2，K562和A431更有效。在多卤代HKAs的2-位上的乙氧羰基具有最高的活性。已发现在间苯二甲腈环上带有三个氟原子的乙氧羰基取代的5o是最有效的衍生物，对五种人类肿瘤细胞系的IC 50值低于3.7μg/ mL，这使其活性比顺铂（DDP）高。
• 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.