1-methyl-3-hydroxy-3-(2-oxo-2-(4-methylphenyl)ethyl)indolin-2-one | 421584-27-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-3-hydroxy-3-(2-oxo-2-(4-methylphenyl)ethyl)indolin-2-one
• 英文别名: 3-hydroxy-1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one；3-hydroxy-1-methyl-3-[2-(4-methylphenyl)-2-oxoethyl]indol-2-one
• CAS: 421584-27-2
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: IOJSSXUBYGMBES-UHFFFAOYSA-N

物化性质

• 沸点：
  560.8±50.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-3-hydroxy-3-(2-oxo-2-(4-methylphenyl)ethyl)indolin-2-one 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  靛红 在 potassium carbonate 、 二乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 12.0h， 生成 1-methyl-3-hydroxy-3-(2-oxo-2-(4-methylphenyl)ethyl)indolin-2-one
  参考文献：
  名称：

  10.002/cmdc.201402038

  摘要：

  DOI：

  10.002/cmdc.201402038

文献信息

• Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with In Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds
  作者：Chhanda Mukhopadhyay、Sayan Pramanik、Suman Ray、Suvendu Maity、Prasanta Ghosh

  DOI：10.1055/a-1384-1967

  日期：2021.7

  An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindole derivatives. The procedure is based on the 1,3-dipolar character of the corresponding diazo compounds under base-catalyzed conditions. The method has a wide substrate scope and uses easily available starting materials.

  开发了一种高效的立体选择性反式环丙烷化反应，用于合成3-烷基亚基氧化吲哚与现场生成的α-重氮羰基化合物或α,β-不饱和重氮化合物的反应，无需金属条件即可合成3-螺环丙基-2-氧化吲哚衍生物。该方法基于相应重氮化合物在碱催化条件下的1,3-偶极特性。该方法具有广泛的底物范围，并使用易于获得的起始材料。

• 10.002/cmdc.201402038
  作者：Nagle, Amrita A.、Reddy, Shridhivya A.、Bertrand, Helene、Tajima, Hisashi、Dang, Truong-Minh、Wong, Siew-Cheng、Hayes, John D.、Wells, Geoffrey、Chew, Eng-Hui

  DOI：10.002/cmdc.201402038

  日期：——
• 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.