1-methyl-1,2-dihydro-2′,10′,16′-trioxaspiro[indole-3,13′-pentacyclo[12.8.0.03,12.04,9.017,22]docosan]-1′(14′),3′(12′),4′(9′),5′,7′,17′(22′),18′,20′-octane-2,11′,15′-trione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-methyl-1,2-dihydro-2′,10′,16′-trioxaspiro[indole-3,13′-pentacyclo[12.8.0.03,12.04,9.017,22]docosan]-1′(14′),3′(12′),4′(9′),5′,7′,17′(22′),18′,20′-octane-2,11′,15′-trione
• 英文别名: 1-methyl spiro[indole-3,7'-[6H,7H,8H]pyrano[3,2-c;5,6-c']di[1]benzopyran]-2(3H),6',8'-trione；1-methylspiro[indolone-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8-trione；1'-Methylspiro[6H,7H,8H-bis[1]benzopyrano[4,3-b:3',4'-e]pyran-7,3'-indoline]-2',6,8-trione；1'-methylspiro[2,10,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4,6,8,17,19,21-octaene-13,3'-indole]-2',11,15-trione
• 化学式: C₂₇H₁₅NO₆
• 分子量: 449.419
• InChiKey: DGVHLNJZBMYUCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-甲基靛红 、 4-羟基香豆素 在 氨基磺酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 以94%的产率得到1-methyl-1,2-dihydro-2′,10′,16′-trioxaspiro[indole-3,13′-pentacyclo[12.8.0.03,12.04,9.017,22]docosan]-1′(14′),3′(12′),4′(9′),5′,7′,17′(22′),18′,20′-octane-2,11′,15′-trione
  参考文献：
  名称：

  氨基磺酸促进功能化螺环 [indoline-3, 7'-pyrano [3, 2-c: 5, 6-c'] dichromene]-2, 6', 8'-trione 衍生物在回流下的快速和无柱色谱合成条件

  摘要：

  开发一个快速和绿色的协议来获取与药学相关和多样化的功能化支架，Spiro [indoline-3,7'-pyrano[3,2- c : 5,6- c ']dichromene]-2,6',8' -trione，基于靛红和 4-羟基香豆素之间的假三组分反应在低成本和环保的固体氨基磺酸催化剂存在下在乙醇水溶液（1:1，v/v）回流条件下完成. 这种新开发的方法的显着特点是无金属一锅合成，使用环保且具有成本效益的溶剂和催化剂，无需柱色谱分离产物，收率高至极好，反应介质和克数可重复使用。规模综合适用性。

  DOI：

  10.1016/j.molstruc.2021.132213

文献信息

• Gold catalyzed double condensation reaction: Synthesis, antimicrobial and cytotoxicity of spirooxindole derivatives
  作者：K. Parthasarathy、Chandrasekar Praveen、J.C. Jeyaveeran、A.A.M. Prince

  DOI：10.1016/j.bmcl.2016.07.036

  日期：2016.9

  Microwave assisted synthesis of spirooxindoles via tandem double condensation between isatins and 4-hydroxycoumarin under gold catalysis is reported. The reaction is practical to perform, since the products can be isolated by simple filtration without requiring tedious column chromatography. The scope of this chemistry is exemplified by preparing structurally diverse spirooxindoles (22 examples) in

  据报道，在金催化下，微波通过靛红与4-羟基香豆素之间的串联双缩合进行微波辅助合成螺硫辛多。该反应是实际可行的，因为可以通过简单的过滤分离产物，而无需繁琐的柱色谱法。通过以优异的产率制备结构多样的螺硫醇（22个实施例）来举例说明该化学作用的范围。对合成化合物的抗菌评估显示，与标准药物相比，三种化合物（3a，3f和3s）显示出显着的MIC值。这些化合物与AmpC-β-内酰胺酶受体的分子对接研究表明3a表现出最小的结合能（-117.819kcal / mol），表明其通过强大的氢键相互作用对氨基酸残基具有很强的亲和力。还评估了所有化合物对COLO320癌细胞的体外细胞毒性。生物测定和分子对接研究表明，就其对CHK1受体的低IC50值（50.0μM）和最少的自由结合能（-8.99kcal / mol）而言，3g是活性最高的化合物。
• Jain; Bhagat; Rajwanshi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 8, p. 633 - 636
  作者：Jain、Bhagat、Rajwanshi、Babu、Sinha

  DOI：——

  日期：——
• Synthesis, antimicrobial and cytotoxic evaluation of spirooxindole[pyrano-bis-2H-l-benzopyrans]
  作者：K. Parthasarathy、Chandrasekar Praveen、K. Saranraj、C. Balachandran、P. Senthil Kumar

  DOI：10.1007/s00044-016-1645-4

  日期：2016.10

  Microwave-assisted tandem double condensation between isatins and 4-hydroxycoumarin under zinc triflate catalysis to afford spirooxindoles in excellent yield is reported. The synthesized compounds were screened for their in vitro antibacterial and antifungal activities. The compounds that showed promising antimicrobial activity (3a, 3j and 3m) were studied for their binding affinity towards AmpC-beta-lactamase receptor, which revealed that compound 3a is highly stabilized by strong hydrogen bond interactions with in the binding pocket. The synthesized spirooxindoles were also evaluated for their cytotoxic potential against COLO320 adenocarcinoma colorectal cancer cells. Biological assay and in silico studies indicated compound 3n as the most active in terms of low IC50 value (50.7 mu M) and least free energy of binding (-8.89 kcal/mol) respectively.
• Sulfamic acid promoted expeditious and column chromatography free synthesis of functionalized spiro [indoline-3, 7′-pyrano [3, 2-c: 5, 6-c'] dichromene]-2, 6′, 8′-trione derivatives under reflux conditions
  作者：Kajal Mal、Chhanda Mukhopadhyay

  DOI：10.1016/j.molstruc.2021.132213

  日期：2022.4

  been accomplished based on a pseudo three-component reaction between isatins and 4-hydroxycoumarin in presence of a low-cost and eco-friendly solid sulfamic acid catalyst in aqueous ethanol (1:1, v/v) under reflux condition. The significant features of this newly developed method are metal-free one pot synthesis, use of eco-friendly and cost-effective solvent and catalyst, no column chromatography involvement

  开发一个快速和绿色的协议来获取与药学相关和多样化的功能化支架，Spiro [indoline-3,7'-pyrano[3,2- c : 5,6- c ']dichromene]-2,6',8' -trione，基于靛红和 4-羟基香豆素之间的假三组分反应在低成本和环保的固体氨基磺酸催化剂存在下在乙醇水溶液（1:1，v/v）回流条件下完成. 这种新开发的方法的显着特点是无金属一锅合成，使用环保且具有成本效益的溶剂和催化剂，无需柱色谱分离产物，收率高至极好，反应介质和克数可重复使用。规模综合适用性。