14-(4-nitrophenyl)-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amine | 1021873-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 14-(4-nitrophenyl)-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amine
• 英文别名: 2-(4-Nitrophenyl)-13-oxa-15-azapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3(12),4,6,8,10,14,16(21)-octaen-22-amine
• CAS: 1021873-85-7
• 化学式: C₂₆H₂₁N₃O₃
• 分子量: 423.471
• InChiKey: ZAYJCQAUIAWUDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.42h， 生成 14-(4-nitrophenyl)-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amine
  参考文献：
  名称：

  以GO-Fc @ Fe 3 O 4纳米杂化物为新型可循环异质纳米催化剂合成2-氨基-3-氰基-4 H-吡喃衍生物，并制备他克林-萘并吡喃杂化物作为AChE抑制剂

  摘要：

  摘要 合成了功能强大且可重复使用的GO-Fc @ Fe 3 O 4纳米杂化体。用间氯过氧苯甲酸（mCPBA）处理氧化石墨烯（GO）片，然后通过GO纳米片与4-二茂铁基丁基胺之间的开环反应，用4-Fc衍生物进行化学修饰。然后，通过将Fe 3 O 4纳米颗粒合成到改性的GO表面获得最终的纳米催化剂。使用不同的分析方法，如FT-IR，XRD，FE-SEM，EDX和VSM技术对GO-Fc @ Fe 3 O 4纳米杂化物的结构和形态进行了表征。然后，2-氨基-3-氰基-4 H-吡喃衍生物（4a – l作为新型多相纳米催化剂，在GO-Fc @ Fe 3 O 4纳米杂化物的存在下，通过多组分反应合成了作为合成前体的三聚氰胺。最后，根据寻找解决阿尔茨海默氏病的方法的重要性，选择14-芳基-10,11,12,14-四氢-9 H-苯并[5,6] chromeno [2,3-b]-喹啉-13作为新的他克林-萘并吡喃杂化物类似物-胺（5a

  DOI：

  10.1007/s13738-020-02125-4

文献信息

• Investigation of the Reaction of <i>o</i>-Aminonitriles with Ketones: A New Modification of Friedländer Reaction and Structures of Its Products
  作者：Jiarong Li、Lijun Zhang、Daxin Shi、Qing Li、Dong Wang、Chunxia Wang、Qi Zhang、Ling Zhang、Yanqiu Fan

  DOI：10.1055/s-2007-1000841

  日期：2008.1

  A new modification of the Friedlander reaction is described and the new byproduct obtained from the reaction of O-aminonitriles and ketones was found to be 2,3-dihydroquinazolin-4(1 H)-one. The mechanism probably involved the formation of an intermediate oxazine, via the Pinner reaction and its transformation into new products via the Dimroth rearrangement.

  描述了 Friedlander 反应的新改进，发现从 O-氨基腈和酮反应中获得的新副产物是 2,3-二氢喹唑啉-4(1 H)-one。该机制可能涉及通过 Pinner 反应形成中间体恶嗪，并通过 Dimroth 重排将其转化为新产物。
• Synthesis, biological assessment and molecular modeling of 14-aryl-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amines
  作者：Emna Maalej、Fakher Chabchoub、Abdelouahid Samadi、Cristóbal de los Ríos、Almudena Perona、Antonio Morreale、José Marco-Contelles

  DOI：10.1016/j.bmcl.2011.02.094

  日期：2011.4

  The synthesis and pharmacological evaluation of racemic 14-aryl-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amines (19-28), prepared by Friedlander reaction of 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitriles (10-18) with suitable cycloalkanones is described. These molecules are potent, in the nanomolar range [IC50 (EeAChE) = 7-101 nM], and selective inhibitors of acetylcholinesterase (AChE). The most potent inhibitor, 4-(13-amino-10,11,12,14-tetrahydro-9H-benzo[5,6] chromeno[2,3-b] quinolin-14-yl) phenol (20) [IC50 (EeAChE) = 7 +/- 2 nM] is four-fold more active than tacrine. Kinetic studies on compound 20 showed that this is a mixed-type inhibitor of EeAChE with a K-i of 5.00 nM. However, racemic 20 was unable to displace propidium iodide, suggesting that the inhibitor does not strongly bind to the peripheral anionic site (PAS) of AChE. Docking, molecular dynamics stimulations, and MM-GBSA calculations agree well with this behavior. (C) 2011 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.