2-N-[(5-N'-isopropylamidino)pyridin-2-yl]isoindolin-1-one hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-N-[(5-N'-isopropylamidino)pyridin-2-yl]isoindolin-1-one hydrochloride
• 英文别名: 1-[(5-N-isopropylamidino)pyridine-2-yl]-2-isoindolinone hydrochloride；6-(3-oxo-1H-isoindol-2-yl)-N'-propan-2-ylpyridine-3-carboximidamide;hydrochloride
• 化学式: C₁₇H₁₈N₄O*ClH
• 分子量: 330.817
• InChiKey: GIWHYFXTZCGDKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-amino-5-(N-isopropylamidino)pyridine hydrochloride 、 邻苯二甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以12%的产率得到5-(N'-isopropylamidino)-N-[2-(5-N'-isopropylamidinopyridin-2-yl)isoindolin-1-ylidene]pyridin-2-amine dihydrochloride
  参考文献：
  名称：

  Novel phenyl and pyridyl substituted derivatives of isoindolines: Synthesis, antitumor activity and DNA binding features

  摘要：

  Novel phenyl-substituted (3a-3d, 4a, 5, 8a, 8b and 9a) and pyridyl-substituted (3e-3i, 4b, 8c-8e, 9b and 9c) isoindolines were prepared in the reaction of o-phthalaldehyde and corresponding substituted aromatic and heteroaromatic amines by modification of reaction conditions from low to high temperature and from neutral to acidic environment.The antiproliferative activity of chosen substituted isoindolines was assessed on a panel of tumour cell lines and normal human fibroblasts. The majority of tested compounds was active at the highest tested concentrations phenyl-substituted isoindolines 3a and 3b and pyridyl-substituted isoindoline 3g showed a selective effect at micromolar concentrations on HepG2 cell line in comparison with other tested tumour cell lines and normal human fibroblasts. The strongest yet non-selective effect was observed for the pyridyl-substituted isoindoline 8c. These isoindoline derivatives showed diverse mechanism of action on tumour cell death induction as compounds 3a and Sc probably induced mitotic catastrophe while compound 3b induced apoptosis. Indeed. DNA binding properties evidenced that compounds 8a, 8c and 8d bind to DNA as highly potent DNA intercalators. By contrast, compounds 3b, 3e, 3i, 4a and 5 did not target the DNA. At last, the phenyl-substituted compound 8b proved to be a strong DNA binding compound with sequence selective binding and without DNA intercalation profile. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.079

文献信息

• Novel phenyl and pyridyl substituted derivatives of isoindolines: Synthesis, antitumor activity and DNA binding features
  作者：Irena Sović、Sandra Kraljević Pavelić、Elitza Markova-Car、Nataša Ilić、Raja Nhili、Sabine Depauw、Marie-Hélène David-Cordonnier、Grace Karminski-Zamola

  DOI：10.1016/j.ejmech.2014.09.079

  日期：2014.11

  Novel phenyl-substituted (3a-3d, 4a, 5, 8a, 8b and 9a) and pyridyl-substituted (3e-3i, 4b, 8c-8e, 9b and 9c) isoindolines were prepared in the reaction of o-phthalaldehyde and corresponding substituted aromatic and heteroaromatic amines by modification of reaction conditions from low to high temperature and from neutral to acidic environment.The antiproliferative activity of chosen substituted isoindolines was assessed on a panel of tumour cell lines and normal human fibroblasts. The majority of tested compounds was active at the highest tested concentrations phenyl-substituted isoindolines 3a and 3b and pyridyl-substituted isoindoline 3g showed a selective effect at micromolar concentrations on HepG2 cell line in comparison with other tested tumour cell lines and normal human fibroblasts. The strongest yet non-selective effect was observed for the pyridyl-substituted isoindoline 8c. These isoindoline derivatives showed diverse mechanism of action on tumour cell death induction as compounds 3a and Sc probably induced mitotic catastrophe while compound 3b induced apoptosis. Indeed. DNA binding properties evidenced that compounds 8a, 8c and 8d bind to DNA as highly potent DNA intercalators. By contrast, compounds 3b, 3e, 3i, 4a and 5 did not target the DNA. At last, the phenyl-substituted compound 8b proved to be a strong DNA binding compound with sequence selective binding and without DNA intercalation profile. (C) 2014 Elsevier Masson SAS. All rights reserved.