2-(3-氯苯基)-4H-异喹啉-1,3-二酮 | 22367-12-0

• 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
• 中文名称: 2-(3-氯苯基)-4H-异喹啉-1,3-二酮
• 英文名称: 2-(3-chlorophenyl)isoquinoline-1,3(2H,4H)-dione
• 英文别名: 2-(3-Chloro-phenyl)-4h-isoquinoline-1,3-dione；2-(3-chlorophenyl)-4H-isoquinoline-1,3-dione
• CAS: 22367-12-0
• 化学式: C₁₅H₁₀ClNO₂
• mdl: MFCD03966867
• 分子量: 271.703
• InChiKey: YILPTMFWSYOSGN-UHFFFAOYSA-N

物化性质

• 溶解度：
  >40.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-(3-氯苯基)-4H-异喹啉-1,3-二酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 phosphorus pentoxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 2-chloro-6a,7-dihydro-5H-dibenzo[b,f]quinolizine-5,12(6H)-dione
  参考文献：
  名称：

  Synthesis and diuretic activity of 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one6-oxime-O-sulfonic acid derivatives

  摘要：

  Using our previously reported 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt 1a (M17055) as a lead, a series of tricyclic (2a-o, 3, 4, 5) and tetracyclic (6) quinolinone oxime O-sulfonic acid derivatives were synthesized by ring annulation of the 1-(2-methylbenzoyl) moiety to the quinolinone skeleton. They were compared with furosemide and compound la for diuretic activity in dogs; some tricyclic 4,5-dihydro-6H-imidazo[4,5,1-ij]quinoline-6-one 6-oxime-O-sulfonic acid derivatives showed diuretic activity comparable (2c,e) or superior (2m) to the lead compound la. These results are discussed on the basis of a comparison of the conformational and electronic characteristics of the relevant compounds with the aid of computer graphics. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80028-2
• 作为产物：
  描述：

  高邻苯二甲酸酐 、 3-氯苯胺 在 溶剂黄146 作用下， 反应 24.0h， 以39%的产率得到2-(3-氯苯基)-4H-异喹啉-1,3-二酮
  参考文献：
  名称：

  NAP-6 和 10-Cl-BBQ、AhR 配体在体外显示选择性乳腺癌细胞毒性的建模和表型筛选

  摘要：

  为了利用芳烃受体 (AhR) 通路在开发乳腺癌特异性细胞毒性化合物中的相互作用，我们检查了乳腺癌的选择性和 AhR 配体 ( Z )-2-(2-氨基苯基)-1的对接姿势ħ -苯并[ DE ]异喹啉-1,3（2 ħ） -二酮（NAP-6; 5）和10氯-7- ħ -苯并[ DE ]苯并[4,5]咪唑并[2,1-一个]异喹啉-7-one (10-Cl-BBQ; 6 )。虽然5 的体外乳腺癌选择性是已知的，但我们围绕这一先导讨论了 SAR，并通过使用表型细胞系筛选和 MTT 测定，首次表明6还具有乳腺癌选择性，特别是在三阴性（TN）受体乳腺癌细胞系 MDA-MB-468、ER+ 乳腺癌细胞系 T47D、ZR-75-1 和 HER2+ 乳腺癌细胞系 SKBR3（GI 50 个值分别为 0.098、0.97、0.13 和 0.21 μM）。事实上，6是55倍更有效在比正常MCF10A乳腺细胞（GI MDA-MB-468细胞50

  DOI：

  10.1002/cmdc.202000721

文献信息

• Superelectrophiles in Synthesis: Preparation of Aromatic Imides
  作者：Sean H. Kennedy、Mark N. Schaeff、Douglas A. Klumpp

  DOI：10.1021/acs.joc.9b01437

  日期：2019.11.1

  Aromatic carboxylic acids are found to undergo reactions with isocyanates, wherein triflic acid promotes the formation of aromatic imide products in fair to good yields. It is proposed that the carboxylic acid group directs the isocyanate electrophile to the ortho-position. This is thought to occur by the formation of a temporary carbamic acid anhydride group, which cleaves upon ortho-functionalization

  发现芳族羧酸与异氰酸酯反应，其中三氟甲磺酸以公平的至良好的产率促进芳族酰亚胺产物的形成。提出羧酸基团将异氰酸酯亲电子体引导至邻位。认为这是通过形成临时氨基甲酸酐基团而发生的，该氨基甲酸酯基团在邻官能化时裂解。合成了一系列酰亚胺产物，并合成了潜在的酪氨酸DNA磷酸二酯酶II选择性抑制剂。
• Flower-shaped ZnO nanoparticles as an efficient, heterogeneous and reusable catalyst in the synthesis of N-arylhomophthalimides and benzannelated isoquinolinones
  作者：Varadhan Krishnakumar、Kesarla Mohan Kumar、Badal Kumar Mandal、Fazlur-Rahman Nawaz Khan

  DOI：10.1007/s11164-012-0511-3

  日期：2012.10

  A simple and green protocol, developed utilizing an efficient, heterogeneous and recyclable catalyst, i.e. zinc oxide nanoparticles (ZnO NPs)-mediated synthesis of N-arylhomophthalimides and benzannelated isoquinolinones, is reported. The structures of the desired products were characterized by FTIR, 1H NMR, 13C NMR, and HRMS techniques. The ZnO NPs exhibited excellent catalytic activity and the proposed methodology is capable of providing the desired products in good yield and purity.

  报道了一种简单且绿色的合成方法，该方法利用一种高效、异质且可回收的催化剂，即氧化锌纳米颗粒（ZnO NPs），进行N-芳基同苯二甲酰亚胺和苯并取代的异喹啉酮的合成。所需产品的结构通过傅里叶变换红外光谱（FTIR）、1H核磁共振（NMR）、13C核磁共振（NMR）和高分辨率质谱（HRMS）技术进行表征。ZnO NPs表现出优异的催化活性，所提出的方法能够以良好的产率和纯度提供所需产品。
• 1,3(2H,4H)-Dioxoisoquinoline-4-carboxamides used as anti-inflammatory
  申请人：Pfizer Inc.

  公开号：US03998954A1

  公开（公告）日：1976-12-21

  1,3(2H,4H)-Dioxoisoquinoline-4-carboxamides, nuclear unsubstituted and substituted, are prepared by reacting the appropriate homophthalimide with potassium cyanate. Secondary carboxamides are prepared by reacting homophthalimide with appropriate isocyanates, and tertiary carboxamides are prepared by aminolysis of 4-carbalkoxy compounds, which are in turn prepared by alcoholysis of the corresponding 4-carboxanilides. Corresponding 5,6,7,8-tetrahydro compounds are similarly prepared. The various 2-substituted homophthalimides are prepared by reacting homophthalic acid with appropriate amine. The 4-carboxamides are anti-inflammatory agents.

  1,3(2H,4H)-二氧化异喹啉-4-羧酰胺，核未取代和取代的，通过将适当的同间苯二酰亚胺与氰酸钾反应制备。次级羧酰胺是通过将同间苯二酰亚胺与适当的异氰酸酯反应制备的，而三级羧酰胺是通过对4-羧烷氧基化合物进行氨解制备的，这些化合物又是通过相应的4-羧基苯胺的醇解制备的。相应的5,6,7,8-四氢化合物同样制备。各种2-取代的同间苯二酰亚胺是通过将同间苯二甲酸与适当的胺反应制备的。4-羧酰胺是抗炎药物。
• Progesterone receptor antagonists with a 3-phenylquinazoline-2,4-dione/2-phenylisoquinoline-1,3-dione skeleton
  作者：Aya Nakagawa、Shigeyuki Uno、Makoto Makishima、Hiroyuki Miyachi、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2008.05.016

  日期：2008.7

  Novel non-steroidal progesterone receptor antagonists with a 3-phenylquinazoline-2,4-dione/2-phenylisoquinoline-1,3-dione skeleton were developed and their structure-activity relationships were investigated. Among the prepared compounds, 4-(4,4-diethyl-3,4-dihydro-1,3-dioxoquinolin-2(1H)yl) benzonitrile (DEPIQ-4CN) showed the most potent activity, with IC50 values of 74-78 nM in alkaline phosphatase activity and reporter gene assays. (c) 2008 Elsevier Ltd. All rights reserved.
• Herbicidal activity of 2-substituted 1,3,4-(2H)-isoquinolinetriones
  作者：Marco Mazza、Tiziana Modena

  DOI：10.1016/s0014-827x(99)00037-3

  日期：1999.6

  A series of 2-substituted 1,3,4-isoquinolinetriones (B) 1-15, precursors of the phthalamic acids and of the 1,3-dihydro-1-hydroxy-3-oxo-1-isobenzofurancarboxamides (F), possessing root antigravitropic activities, were prepared and evaluated for herbicidal activity on weeds and crops. Among the compounds examined, several derivatives were very active against weeds, in many cases more active than the commercially available herbicides used as the reference standards. Phytotoxicities on crops, selectivity and persistence of herbicidal effect were observed. (C) 1999 Elsevier Science S.A. All rights reserved.