2,3-dihydroimidazo[1,2-b]isoquinoline-5(1H)-one | 25113-57-9

• 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: 2,3-dihydroimidazo[1,2-b]isoquinoline-5(1H)-one
• 英文别名: 2,3-dihydroimidazo<1,2-b>isoquinolin-5(1H)-one；2,3-dihydroimidazo[1,2-b]isoquinolin-5(1H)-one；5-Oxo-1,2,3,5-tetrahydroiminazo<1,2-b>isoquinolin；5-Oxo-1.2.3.5-tetrahydro-imidazo<1.2-b>isochinolin；1,2,3,5-Tetrahydroimidazo-<1,2-b>-isochinolin-5-on；2,3-dihydro-1H-imidazo[1,2-b]isoquinolin-5-one；2,3-dihydro-1H-imidazo[1,2-b]isoquinolin-5-one
• CAS: 25113-57-9
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: IGCOPIWHEYBFST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydroimidazo[1,2-b]isoquinoline-5(1H)-one 在 三乙胺 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 2.83h， 生成
  参考文献：
  名称：

  Antimalarial activity of novel imidazoisoquinolinone derivatives correlates with heme binding affinity

  摘要：

  A series of novel imidazoisoquinolinone derivatives were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive GHA strain of Plasmodium falciparum. Compounds 2, 4, 6, 9, and 17 revealed moderate to good activities in the micromolar range. Binding interaction between these active compounds and heme were determined and correlated with antimalarial activity. A good correlation (r = 0.98) was observed between antimalarial activity and the heme dissociation constants (K (d)). These suggest that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation.

  DOI：

  10.1007/s00044-014-1231-6
• 作为产物：
  描述：

  邻羧基苯乙酸 、 乙二胺 反应 0.1h， 以96%的产率得到2,3-dihydroimidazo[1,2-b]isoquinoline-5(1H)-one
  参考文献：
  名称：

  Synthesis of 2,3-Dihydroimidazo[1,2-b]isoquinoline-5(1H)-one and Derivatives

  摘要：

  微波辐照下2,3-二氢咪唑并[1,2-b]异喹啉-5(1H)-酮的新颖高效合成方法被报道。通过使用DMAP作为催化剂进行酰化反应，合成了几种新的2,3-二氢咪唑并[1,2-b]异喹啉-5(1H)-酮衍生物。利用HPLC进行的动力学研究确定了形成的N-和C-酰化异构体。

  DOI：

  10.1055/s-2005-918505

文献信息

• Condensed Heterotricycles. Synthesis and Reactions ofb-Fused 1(2H)-Isoquinolinones with unusual enaminic properties
  作者：Kuppuswamy Nagarajan、Vunnam R. Rao、Rashmi K. Shah、Sharada J. Shenoy、Hans Fritz、Wilhelm J. Richter、Dieter Muller

  DOI：10.1002/hlca.19880710110

  日期：1988.2.3

  Homophthalic acid (1) undergoes reaction with 1,2-, 1,3-, and 1,4-diamines to give condensed 1(2H)-isoquinolinones like 2, 4, 13, and 25, which exhibit marked enamine character. These are attacked by electrophiles at the N or C terminus. Some notable reactions of imidazoisoquinolone 2 are those with maleic and acrylic acids to form the tetracycles 48 and 51, respectively. With propiolic acid, 5 underwent

  高邻苯酸（1与1,2-，1,3-，和1,4-二胺）经历反应，得到稠合1（2 ħ）异喹啉酮等2，4，13，和25，其显示出标记烯胺字符。它们在N或C末端受到亲电试剂的攻击。咪唑并异喹诺酮2的一些值得注意的反应是与马来酸和丙烯酸的反应，分别形成四环48和51。与丙酸5进行了有趣的反应，形成苯并咪唑并萘啶53。从2引出了同样有趣的行为在其与甲醛的反应中，除了预期的亚甲基桥连分子59之外，新型螺环衍生物60是通过假定的氮杂二烯中间体63的二聚作用形成的。
• Identification of potent bovine viral diarrhea virus inhibitors by a structure-based virtual screening approach
  作者：Eliana F. Castro、Juan J. Casal、María J. España de Marco、Leandro Battini、Matías Fabiani、Gabriela A. Fernández、Ana M. Bruno、Lucía V. Cavallaro、Mariela Bollini

  DOI：10.1016/j.bmcl.2018.11.041

  日期：2019.1

  small molecules from commercial and in-house databases were evaluated and several structurally different compounds were tested in vitro for antiviral activity. Interestingly, of twelve evaluated compounds, five were active and displayed EC50 values in the sub and low-micromolar range. Time of drug addition experiment and measured intracellular BVDV RNA showed that compound 7 act during RNA synthesis. Molecular

  牛病毒性腹泻病毒（BVDV）是一种瘟病毒，其在牛中的感染在全球范围内分布。抗病毒药的使用可以补充疫苗接种作为控制手段，并减少经济损失。病毒的RNA依赖性RNA聚合酶（RdRp）对于其基因组复制是必不可少的，并且构成了抗病毒药物鉴定的诱人靶标。为了获得选择性的BVDV抑制剂，使用BVDV RdRp的晶体结构进行虚拟筛选。对来自商业数据库和内部数据库的大约15,000个小分子进行了评估，并在体外测试了几种结构不同的化合物的抗病毒活性。有趣的是，在十二种被评估化合物中，有五种处于活性状态并显示出EC 50值在亚微摩尔和低微摩尔范围内。药物添加实验和测量细胞内BVDV RNA的时间表明，化合物7在RNA合成过程中起作用。进行了分子动力学和MM / PBSA计算以表征最具活性的化合物与RdRp的相互作用，这将使将来的配体优化成为可能。这些研究突出了计算机筛选技术的使用，以鉴定一类新的BVDV抑制剂。
• Microwave-assisted rapid and efficient synthesis of C-alkyl imidazoisoquinolinone derivatives
  作者：Mariela Bollini、Mariángeles González、Ana María Bruno

  DOI：10.1016/j.tetlet.2009.01.083

  日期：2009.4

  The synthesis of a set of 10-benzyl-2,3-dihydroimidazo[1,2-b]isoquinolin-5(1H)-one and 5-oxo-imidazo[1,2-b]isoquinolin-10-yl)-N-phenylacetamide derivatives was achieved by exposing the corresponding alkylating agent and imidazoisoquinolinone to microwave irradiation and traditional oil bath heating in the presence of K2CO3 and DMAP. The microwave technique as well as DMAP as base accelerated the alkylation

  一组10-苄基-2,3-二氢咪唑并[1,2- b ]异喹啉-5（1 H）-一和5-氧代咪唑并[1,2 - b ]异喹啉-10-基的合成- ñ苯基乙酰胺衍生物是通过将相应的烷基化剂和imidazoisoquinolinone微波照射和传统的油浴中加热以K的存在下实现2 CO 3和DMAP。微波技术以及以DMAP为基础的烷基化反应加快了2–6分钟，产生了79–88％的收率。
• [EN] PROCESS FOR MAKING AZO-PIGMENTS
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：WO1990015844A1

  公开（公告）日：1990-12-27

  (DE) Die praxisübliche Produktion von Monoazoverbindungen auf Basis von Dichlor- und Trichloranilinen bzw. von Disazoverbindungen der chlorierten Biphenylreihe nach den herkömmlichen Kupplungsmethoden stößt insofern auf Schwierigkeiten, als die resultierenden Pigmente durch Spuren von polychlorierten Biphenylen verunreinigt sind. Erfindungsgemäß wurde nun gefunden, daß sich durch den Zusatz von wasserlöslichen Olefinen vom Typ (I) (R = H, Alk, OAlk; X = -COOR1, -CONHR2 oder -NR3COR4) bei der Azokupplung die PCB-bildenden Nebenreaktionen während der Pigmentsynthese entscheidend zurückdrängen lassen.(EN) The conventional production of monoazo compounds based on dichloro and trichloroanilines or of diazo compounds in the chlorinated biphenyl series by the prior art coupling methods encounters difficulties if the resultant pigments are polluted by traces of polychlorinated biphenyls. According to the invention, it has now been discovered that the PCB-forming side-reactions during pigment synthesis can be substantially repressed by the addition of water-soluble olefines of formula (I) type (R = H, Alk, OAlk; X = COOR1, -CONHR2 or NR3COR4) in the azo coupling.(FR) La production, couramment réalisée dans la pratique, de composés monoazoïques à base de dichloro- et de trichloro- anilines, ou encore, de composés disazoïques de la série chlorée du biphényle, suivant les méthodes de copulation traditionnelles, se heurte à des difficultés, du fait que les pigments résultants sont contaminés par des traces de biphénylène polychloré. Conformément à l'invention, on a trouvé que l'addition d'oléfines solubles dans l'eau du type (I) (R = H, Alc, OAlc; X = COOR1, -COHNR2 ou -NR3COR4) permettait d'écarter de façon déterminante, pendant la synthèse des pigments, les réactions secondaires conduisant à la formation de BPC (biphénylène polychloré) lors de la copulation azoïque.

  （DE）在基于氯化物和二氯苯胺的单arro compounds 或二romo苯系中的 Diazonium compounds 的常规生产过程中，通过传统方法 coupling 得到的最终色料会受到多氯 biphenylene 的跟随物的污染。按照发明，人们已经发现，可以通过添加根据(I)型水溶性烯烃( 其中 R = H、Alk、OAlk; X = COOR1、-CO_NHR2或 NR3COR4 )，把由于 side reactions 形成的 PCB 汇集于 pigment 合成阶段，从而有效阻止这些副反应。(EN) The conventional production of monoazo compounds based on dichloro and trichloroanilines or of diazo compounds in the chlorinated biphenyl series by the prior art coupling methods encounters difficulties if the resultant pigments are polluted by traces of polychlorinated biphenyls. According to the invention, it has now been discovered that the PCB-forming side-reactions during pigment synthesis can be substantially repressed by the addition of water-soluble olefines of formula (I) type (R = H, Alk, OAlk; X = COOR1, -CONHR2 or NR3COR4) in the azo coupling.(FR) La production, couramment réalisée dans la pratique, de composés monoazoïques à base de dichloro- et de trichloro- anilines, ou encore, de composés disazoïques de la série chlorée du biphényle, suivant les méthodes de copulation traditionnelles, se heurte à des difficultés, du fait que les pigments résultants sont contaminés par des traces de biphénylène polychloré. Conformément à l'invention, on a trouvé que l'addition d'oléfines solubles dans l'eau du type (I) (R = H, Alc, OAlc; X = COOR1, -COHNR2 ou -NR3COR4) permettait d'écarter de façon déterminante, pendant la synthèse des pigments, les réactions secondaires conduisant à la formation de BPC (biphénylène polychloré) lors de la copulation azoïque.
• New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure–activity relationships
  作者：Mariela Bollini、Juan José Casal、Diego E. Alvarez、Lucía Boiani、Mercedes González、Hugo Cerecetto、Ana María Bruno

  DOI：10.1016/j.bmc.2009.01.011

  日期：2009.2

  A series of novel benzoimidazo andN-aryl-5-oxo-imidazo[1,2-b] isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed. (c) 2009 Elsevier Ltd. All rights reserved.