(E)-1-methyl-3-(2-(naphthalen-2-yl)-2-oxoethylidene)indolin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-1-methyl-3-(2-(naphthalen-2-yl)-2-oxoethylidene)indolin-2-one
• 英文别名: (3E)-1-methyl-3-(2-naphthalen-2-yl-2-oxoethylidene)indol-2-one
• 化学式: C₂₁H₁₅NO₂
• 分子量: 313.356
• InChiKey: XPBYSKLMIWRECP-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-3-(2-(naphthalen-2-yl)-2-oxoethylidene)indolin-2-one 、 苄基叠氮 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以62%的产率得到1'-benzyl-1,1''-dimethyl-4',5'-bis[(naphthalen-2-yl)carbonyl]-1,1'',2,2''-tetrahydrodispiro[indole-3,2'-pyrrolidine-3',3''-indole]-2,2''-dione
  参考文献：
  名称：

  Lewis Acid Catalyzed Unprecedented [3 + 2] Cycloaddition Yields 3,3′-Pyrrolidinyldispirooxindoles Containing Four Contiguous Chiral Stereocenters with Two Contiguous Quaternary Spirostereocenters

  摘要：

  A Lewis acid catalyzed domino reaction cascades through azide-alkene cycloadclition, rearrangement, aziridine ring opening, and azomethine cycloaddition with a parent dipolarophile, resulting in 3,3'-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters.

  DOI：

  10.1021/ol501547p
• 作为产物：
  描述：

  2-萘乙酮 在 盐酸 、 二乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 (E)-1-methyl-3-(2-(naphthalen-2-yl)-2-oxoethylidene)indolin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents

  摘要：

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.056

文献信息

• Difluorocarbene-Enabled Synthesis of 3-Alkenyl-2-oxindoles from <i>ortho</i>-Aminophenylacetylenes
  作者：Shanglin Chen、Hua Huang、Xin Li、Xingxing Ma、Jianke Su、Qiuling Song

  DOI：10.1021/acs.orglett.3c00150

  日期：2023.2.24

  cyclization pathway from difluorocarbene and ortho-amino aryl alkynone, rendering an effective and universal strategy for the construction of 3-alkenyl-2-oxindoles. Our strategy starts from cheap and accessible ortho-amino aryl alkynone instead of the direct indole skeleton; moreover, in situ generated difluorocarbene from commercially available halogenated difluoroalkylative reagents enables the cleavage

  在此，我们报道了一种来自二氟卡宾和邻氨基芳基炔酮的无过渡金属 [4 + 1] 环化途径，为构建 3-烯基-2-羟吲哚提供了一种有效且通用的策略。我们的策略从廉价易得的邻氨基芳基炔酮开始，而不是直接的吲哚骨架；此外，从市售的卤化二氟烷基化试剂中原位生成的二氟卡宾能够裂解 C-N 键并形成新的 C-N 键和 C-C 键。
• Synthesis and biological evaluation of spiro[cyclopropane-1,3′-indolin]-2′-ones as potential anticancer agents
  作者：Chada Narsimha Reddy、V. Lakshma Nayak、Geeta Sai Mani、Jeevak Sopanrao Kapure、Praveen Reddy Adiyala、Ram Awatar Maurya、Ahmed Kamal

  DOI：10.1016/j.bmcl.2015.08.056

  日期：2015.10

  Libraries of spiro[cyclopropane-1,3'-indolin]-2'-ones were synthesized and evaluated for their biological activity against five different human cancer cell lines HT-29 (colon cancer), DU-145 (prostate cancer), Hela (cervical cancer), A-549 (Lung cancer), and MCF-7 (breast cancer). Many compounds of the series exhibited promising anticancer activity (IC50 < 20 mu M) against the studied cell lines. Based on the screening results, a structure activity relationship (SAR) of the pharmacophore was proposed. Among the series compound 6b and 6u showed significant activity against human prostate cancer cell line, DU-145. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G0/G1 phase leading to caspase-3 dependent apoptotic cell death. Further, measurement of mitochondrial membrane potential and Annexin V-FITC assay also suggested that 6b and 6u induced cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.
• Lewis Acid Catalyzed Unprecedented [3 + 2] Cycloaddition Yields 3,3′-Pyrrolidinyldispirooxindoles Containing Four Contiguous Chiral Stereocenters with Two Contiguous Quaternary Spirostereocenters
  作者：Koorathota Suman、Lanka Srinu、Sathiah Thennarasu

  DOI：10.1021/ol501547p

  日期：2014.7.18

  A Lewis acid catalyzed domino reaction cascades through azide-alkene cycloadclition, rearrangement, aziridine ring opening, and azomethine cycloaddition with a parent dipolarophile, resulting in 3,3'-pyrrolidinyldispirooxindoles containing four contiguous chiral stereocenters with two contiguous quaternary spirostereocenters.