(S)-methyl 2-(1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanotate | 363165-79-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-methyl 2-(1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanotate
• 英文别名: (S)-2-(1,3-dihydro-isoindol-2-yl)-3-(1H-indol-3-yl)-propionic acid methyl ester；methyl (2S)-2-(1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanoate
• CAS: 363165-79-1
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: COZVLRNOJOPHTK-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanotate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (S)-2-(1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanoic acid
  参考文献：
  名称：

  新型异吲哚基-和双异吲哚基苯基硼酸酐的合成，表征。硼和异吲哚啉化合物对胶质母细胞瘤细胞和小胶质细胞测定的抗增殖活性

  摘要：

  由于硼化合物的合成发展和出色的生物学活性，其重要性日益提高，因此，本文介绍的研究重点是新型异吲哚基苯基硼酸酐（2a，2c和2e）和双异吲哚基苯基硼酸酐（2b和2b ）的合成。2d），以及它们及其前体（a - e），1（a - e）对胶质母细胞瘤细胞U373的抗增殖活性以及对正常小胶质细胞的细胞毒活性的比较研究。所有化合物均通过光谱法进行了表征。1个H，13 C，11 B NMR，IR和HRMS。在2b和2d的可变温度下的1 H和11 B NMR数据显示，由于分子内N→B配位和去配位键，在包含四面体和三角硼原子的物质之间达到平衡。B衍生物前沿分子轨道的研究表明2b'和2d'是比2a，2c和2e硬的分子，因此可以与第二个异吲哚啉反应获得2b和2d。而钾的HOMO位点衍生出1bK和1dK在NCHCO 2 K部分上，因此与2b '和2d'反应以获得2b和2d。这些结果阐明了与试剂的等分子比无关地获得2a

  DOI：

  10.1016/j.jorganchem.2019.04.011
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 、 1,2-二(溴甲基)苯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以80%的产率得到(S)-methyl 2-(1,3-dihydroisoindol-2-yl)-3-(1H-indol-3-yl)propanotate
  参考文献：
  名称：

  Partition coefficient determination of a series of isoindolines-2-substituted and its correlation with their antiproliferative activity on HeLa cells

  摘要：

  In this study, the partition coefficients (Log P) of two series of isoindolines-2-substituted were calculated from the equation obtained for the multilinear correlation between the electronic properties: the highest occupied molecular orbital and the lowest unoccupied molecular orbital energies, and the steric property volume, and the experimental Log P values were determined for some representative isoindolines. Log P values calculated under quantum chemistry were compared with Log P values obtained by the Log P calculation software ALOGPS 2.1 server; the Log P values calculated showed a better correlation with experimental Log P values than those obtained by means of the software. Log P values calculated were also correlated with the antiproliferative activity of some isoindolines-2-substituted determined on HeLa cells, and the correlation obtained shows a quadratic relationship between Log P values calculated and the antiproliferative activity of isoindolines-2-substituted, suggesting a significant effect of Log P values on biological activity of isoindolines.

  DOI：

  10.1007/s00044-012-0399-x

文献信息

• WO2007/7054
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] PHTHALAMIDES, SUCCINIMIDES AND RELATED COMPOUNDS AND THEIR USE AS PHARMACEUTICALS<br/>[FR] PHTHALAMIDES, SUCCINIMIDES, COMPOSES APPARENTES ET LEUR UTILISATION EN TANT QUE PRODUITS PHARMACEUTIQUES
  申请人：CANCER REC TECH LTD

  公开号：WO2007007054A1

  公开（公告）日：2007-01-18

  [EN] The present invention relates to certain phthalamides, succinimides and related compounds and their use as pharmaceuticals. In particular, the present invention relates to these compounds, pharmaceutical compositions comprising these compounds, and use of these compounds, for example, to inhibit DNA methylation in cells, particularly tumour cells.
  [FR] L'invention concerne certains phthalamides, succinimides et composés apparentés et leur utilisation en tant que produits pharmaceutiques. L'invention porte notamment sur ces composés, sur des compositions pharmaceutiques comprenant ces composés et sur l'utilisation de ces composés, par exemple pour inhiber la méthylation de l'ADN dans des cellules, notamment des cellules tumorales.
• Partition coefficient determination of a series of isoindolines-2-substituted and its correlation with their antiproliferative activity on HeLa cells
  作者：Cynthia R. Trejo Muñoz、Teresa Mancilla Percino、Elvia Mera Jiménez、José Correa-Basurto、José G. Trujillo Ferrara

  DOI：10.1007/s00044-012-0399-x

  日期：2013.8

  In this study, the partition coefficients (Log P) of two series of isoindolines-2-substituted were calculated from the equation obtained for the multilinear correlation between the electronic properties: the highest occupied molecular orbital and the lowest unoccupied molecular orbital energies, and the steric property volume, and the experimental Log P values were determined for some representative isoindolines. Log P values calculated under quantum chemistry were compared with Log P values obtained by the Log P calculation software ALOGPS 2.1 server; the Log P values calculated showed a better correlation with experimental Log P values than those obtained by means of the software. Log P values calculated were also correlated with the antiproliferative activity of some isoindolines-2-substituted determined on HeLa cells, and the correlation obtained shows a quadratic relationship between Log P values calculated and the antiproliferative activity of isoindolines-2-substituted, suggesting a significant effect of Log P values on biological activity of isoindolines.
• Synthesis, characterization of novel isoindolinyl- and bis-isoindolinylphenylboronic anhydrides. Antiproliferative activity on glioblastoma cells and microglial cells assays of boron and isoindolines compounds
  作者：Teresa Mancilla Percino、José Eduardo Guzmán Ramírez、Elvia Mera Jiménez、Cynthia Raquel Trejo Muñoz

  DOI：10.1016/j.jorganchem.2019.04.011

  日期：2019.8

  Boron compounds importance have been raising due to the development of its synthesis and remarkable biological activities, so in this manner the study here presented is focused on the synthesis of novel isoindolinylphenylboronic anhydrides (2a, 2c and 2e) and bis-isoindolinylphenylboronic anhydrides (2b and 2d), as well as a comparative study of the antiproliferative activity of these and their precursors

  由于硼化合物的合成发展和出色的生物学活性，其重要性日益提高，因此，本文介绍的研究重点是新型异吲哚基苯基硼酸酐（2a，2c和2e）和双异吲哚基苯基硼酸酐（2b和2b ）的合成。2d），以及它们及其前体（a - e），1（a - e）对胶质母细胞瘤细胞U373的抗增殖活性以及对正常小胶质细胞的细胞毒活性的比较研究。所有化合物均通过光谱法进行了表征。1个H，13 C，11 B NMR，IR和HRMS。在2b和2d的可变温度下的1 H和11 B NMR数据显示，由于分子内N→B配位和去配位键，在包含四面体和三角硼原子的物质之间达到平衡。B衍生物前沿分子轨道的研究表明2b'和2d'是比2a，2c和2e硬的分子，因此可以与第二个异吲哚啉反应获得2b和2d。而钾的HOMO位点衍生出1bK和1dK在NCHCO 2 K部分上，因此与2b '和2d'反应以获得2b和2d。这些结果阐明了与试剂的等分子比无关地获得2a