3-Amino-1-(3,4-dichloro-phenyl)-1H-benzo[f]chromene-2-carbonitrile | 875132-82-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-Amino-1-(3,4-dichloro-phenyl)-1H-benzo[f]chromene-2-carbonitrile
• 英文别名: 3-amino-1-(3,4-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
• CAS: 875132-82-4
• 化学式: C₂₀H₁₂Cl₂N₂O
• 分子量: 367.234
• InChiKey: OOGZNCRSMWNCSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Amino-1-(3,4-dichloro-phenyl)-1H-benzo[f]chromene-2-carbonitrile 在 羟胺 、 三乙胺 作用下， 以 乙酸酐 、 甲苯 为溶剂， 反应 8.0h， 生成 12-(3,4-Dichloro-phenyl)-11-imino-11H,12H-7-oxa-8,10-diaza-benzo[a]anthracen-10-ol
  参考文献：
  名称：

  伯胺和羟胺对乙氧基亚甲基氨基萘吡喃的作用：新型萘吡喃 [2,3-d] 嘧啶衍生物的合成

  摘要：

  多种萘并吡喃 1 已通过 2-萘酚与芳基（或烷基）亚戊二腈反应制备。萘并吡喃与原甲酸三乙酯，然后与伯胺和羟胺反应，生成新的萘吡并 [2, 3-d] 嘧啶 3 和 4，其结构经红外光谱和核磁共振光谱证实。

  DOI：

  10.1515/hc.2005.11.2.139
• 作为产物：
  描述：

  2-(3,4-dichlorobenzylidene)malononitrile 、 2-萘酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以79%的产率得到3-Amino-1-(3,4-dichloro-phenyl)-1H-benzo[f]chromene-2-carbonitrile
  参考文献：
  名称：

  伯胺和羟胺对乙氧基亚甲基氨基萘吡喃的作用：新型萘吡喃 [2,3-d] 嘧啶衍生物的合成

  摘要：

  多种萘并吡喃 1 已通过 2-萘酚与芳基（或烷基）亚戊二腈反应制备。萘并吡喃与原甲酸三乙酯，然后与伯胺和羟胺反应，生成新的萘吡并 [2, 3-d] 嘧啶 3 和 4，其结构经红外光谱和核磁共振光谱证实。

  DOI：

  10.1515/hc.2005.11.2.139

文献信息

• Iodine mediated synthesis of coumarins from chromenes
  作者：Himanshu Sharma、Mohini Mourya、Lokesh K. Soni、Debanjan Guin、Yogesh C. Joshi、Mahaveer P. Dobhal、Ashok K. Basak

  DOI：10.1016/j.tetlet.2015.11.019

  日期：2015.12

  Iodine mediated rapid conversion of 2-amino-3-cyano-4-aryl-4H chromenes to the corresponding coumarins in the presence of water is described. Several chromenes are obtained in high yields without chromatographic purification. Under anhydrous conditions, 2-iminochromenes are obtained as major products. (C) 2015 Elsevier Ltd. All rights reserved.
• Nontoxic and Neuroprotective β-Naphthotacrines for Alzheimer’s Disease
  作者：Mario Esquivias-Pérez、Emna Maalej、Alejandro Romero、Fakher Chabchoub、Abdelouahid Samadi、José Marco-Contelles、María Jesús Oset-Gasque

  DOI：10.1021/tx400138s

  日期：2013.6.17

  The synthesis, toxicity, neuroprotection, and human acetylcholinesterase (hAChE) / human butyrylcholinesterase (hBuChE) inhibition properties of beta-naphthotacrines 1-14 as new drugs for Alzheimer's disease (AD) potential treatment, are reported. beta-Naphthotacrines 1-14 showed lower toxicity than tacrine; moreover, at the highest concentration assayed (300 mu M) compounds 7, 10 and 11 displayed 2.25-2.01-fold higher cell viability than tacrine in HepG2 cells. A neuroprotective effect was observed for compounds 10 and 11 in a neuronal cortical culture exposed to a combination of oligomycin A/rotenone. An efficient and selective inhibition of hAChE, was only observed for the beta-naphthotacrines bearing electron-donating substituents at the aromatic ring, beta-naphthotacrine 10 being the most potent (hAChE: IC50 = 0.083 +/- 0.024 mu M). Kinetic inhibition analysis clearly demonstrated that beta-naphthotacrine 10 behaves as a mixed-type inhibitor (K-i2 = 0.72 +/- 0.06 mu M) at high substrate concentrations (0.5-10 mu M), while at low concentrations (0.01-0.1 mu M) it behaves as a hAChE competitive inhibitor (K-i1 = 0.007 +/- 0.001 mu M). These findings identified beta-naphthotacrine 10 as a potent and selective hAChE inhibitor in a nanomolar range, with toxicity lower than that of tacrine both in human hepatocytes and rat cortical neurons, with a potent neuroprotective activity and, consequently, an attractive multipotent active molecule of potential application in AD treatment.
• ACTION OF PRIMARY AMINES AND HYDROXYLAMINE ON ETHOXYMETHYLENEAMINONAPHTOPYRANES: SYNTHESIS OF NEW NAPHTOPYRANO [2,3-d] PYRIMIDINES DERIVATIVES
  作者：Mehadi Messaád、Fakher Chabchoub、Mansour Salem

  DOI：10.1515/hc.2005.11.2.139

  日期：2005.1

  A variety of naphtopyrans 1 has been prepared by reaction of 2-naphtol with aryl (or alkyl) idenemalononitriles. The reaction of the naphtopyrans with triethylorthoformiate and then with primary amines and hydroxylamine, leads to new naphtopyrano [2, 3-d] pyrimidines 3 and 4, whose structures were confirmed by IR and NMR spectroscopy.

  多种萘并吡喃 1 已通过 2-萘酚与芳基（或烷基）亚戊二腈反应制备。萘并吡喃与原甲酸三乙酯，然后与伯胺和羟胺反应，生成新的萘吡并 [2, 3-d] 嘧啶 3 和 4，其结构经红外光谱和核磁共振光谱证实。