4-(2-咪唑啉基)苯胺盐酸盐 | 61033-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-咪唑啉基)苯胺盐酸盐
• 中文别名: 4-(4,5-二氢-1H-咪唑-2-基)苯胺盐酸盐
• 英文名称: 2-(4-aminophenyl)-4,5-dihydro-1H-imidazole hydrochloride
• 英文别名: 4-(imidazolin-2-yl)aniline hydrochloride；4-(2-imidazolynyl)aniline hydrochloride；4-(2-imidazolinyl)aniline hydrochloride；4-(4,5-Dihydro-1H-imidazol-2-yl)aniline hydrochloride；4-(4,5-dihydro-1H-imidazol-2-yl)aniline;hydrochloride
• CAS: 61033-86-1
• 化学式: C₉H₁₁N₃*ClH
• 分子量: 197.667
• InChiKey: SHDZIGFWOKNAKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.4
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  4-(2-咪唑啉基)苯胺盐酸盐 、 邻苯二甲醛 以 乙醇 为溶剂， 反应 8.0h， 以20%的产率得到4-(imidazolin-2-yl)-N-{2-[4-(imidazolin-2-yl)phenyl]isoindolin-1-ylidene}benzenamine 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
• 作为产物：
  描述：

  对氨基苯腈 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4-(2-咪唑啉基)苯胺盐酸盐
  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

• Identification of New FLT3 Inhibitors That Potently Inhibit AML Cell Lines via an Azo Click-It/Staple-It Approach
  作者：Xiaochu Ma、Jie Zhou、Changhao Wang、Brandon Carter-Cooper、Fan Yang、Elizabeth Larocque、Jonathan Fine、Genichiro Tsuji、Gaurav Chopra、Rena G. Lapidus、Herman O. Sintim

  DOI：10.1021/acsmedchemlett.6b00468

  日期：2017.5.11

  Acute myeloid leukemia (AML) is an aggressive malignancy with only a handful of therapeutic options. About 30% of AML patients harbor mutated FLT3 kinase, and thus, this cancer-driver has become a hotly pursued AML target. Herein we report a new class of FLT3 inhibitors, which potently inhibit the proliferation of acute myeloid leukemia (AML) cells at nanomolar concentrations.
• Antiproliferative potency of novel benzofuran-2-carboxamides on tumour cell lines: Cell death mechanisms and determination of crystal structure
  作者：Marijana Hranjec、Irena Sović、Ivana Ratkaj、Gordana Pavlović、Nataša Ilić、Linda Valjalo、Krešimir Pavelić、Sandra Kraljević Pavelić、Grace Karminski-Zamola

  DOI：10.1016/j.ejmech.2012.11.009

  日期：2013.1

  In this manuscript the synthesis and biological activity of novel heterocyclic derivatives of benzofuran-2-carboxamides 3a-j and 6a-f is presented. Biological evaluation in vitro revealed that only few compounds exerted concentration-depended antiproliferative effects on tumour cell lines at micromolar concentrations. In particular, 2-imidazolynyl substituted compound 6f showed selectivity on SK-BR-3 cell line while 2-N-acetamidopyridyl substituted 3h and 2-imidazolynyl substituted amide 3i showed selective concentration-dependent antiproliferative effects on SW620 cell line. Compounds 3h and 61 induced apoptosis while compound 3i acted through a cell death mechanism other than apoptosis. (C) 2012 Elsevier Masson SAS. All rights reserved.