3-amino-1-(2,6-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrile | 314767-77-6

• 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-(2,6-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
• CAS: 314767-77-6
• 化学式: C₂₀H₁₂Cl₂N₂O
• 分子量: 367.234
• InChiKey: REKUJRBFJCMPFY-UHFFFAOYSA-N

物化性质

• 沸点：
  547.8±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

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-(2,6-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrile 、 环己酮 生成 2-(2,6-Dichlorophenyl)-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
  参考文献：
  名称：

  Nontoxic and Neuroprotective β-Naphthotacrines for Alzheimer’s Disease

  摘要：

  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.

  DOI：

  10.1021/tx400138s
• 作为产物：
  描述：

  2,6-二氯苯甲醛 、 2-萘酚 、 丙二腈 在 copper-[2-({3-[(2-aminoethyl)thio]propyl}thio)ethyl]amine complex supported on NaY nanozeolite nanocatalyst 作用下， 以 乙醇 、 水 为溶剂， 以99%的产率得到3-amino-1-(2,6-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
  参考文献：
  名称：

  固定在纳米 NaY 沸石上的铜-胺络合物作为可回收的纳米催化剂用于环境友好地合成 2-氨基-4H-色烯

  摘要：

  通过用 3-氯丙基三甲氧基硅烷 (CPTMS) 和 [2-({3-[(2-氨基乙基)硫代]丙基}硫代)乙基]胺对纳米 NaY 沸石进行后改性制备纳米 NaY 沸石负载的铜-胺络合物然后与Cu（I）离子配位。各种技术，如傅里叶变换红外光谱 (FT-IR)、X 射线粉末衍射 (XRD)、动态光散射 (DLS)、热重分析 (TGA)、差热分析 (DTA)、扫描电子显微照片 (SEM)、透射电子显微镜 （TEM)、Brunauer-Emmett-Teller (BET)、t-plot、能量色散光谱 (EDS)、电感耦合等离子体 (ICP) 和元素分析用于表征合成催化剂的结构。合成的纳米样品的催化活性在 2-氨基-4 H的三组分合成中进行了评估-色烯衍生物，在绿色条件下产生高反应产率和短反应时间。催化剂通过过滤分离，可重复使用至少七次连续运行而不会显着损失催化活性。沸石表面负载的 [2-({3-[(

  DOI：

  10.1002/aoc.6886

文献信息

• One-pot synthesis of chromenes in the presence of nano-cellulose/Ti^(IV)/Fe₃O₄ as natural-based magnetic nano-catalysts under solvent free conditions
  作者：Raziyeh Gholami、Abdolhamid Bamoniri、Bi Bi Fatemeh Mirjalili

  DOI：10.1039/d2ra05057a

  日期：——

  such as XRD, SEM, FT-IR, BET, EDX, TEM, TGA and VSM were used to characterize the catalysts. Then, the identified catalysts were used for the synthesis of various chromene skeletons via reaction of malononitrile, aldehyde and dimedone, 4-hydroxycoumarine or 2-naphthole at 70 °C under solvent free conditions. The spectroscopic methods used to determine the structure of the products include 13C NMR, 1H NMR

  本研究研究了以纤维素/Ti(IV)/Fe3O4为名的纳米纤维素上稳定的四氯化钛磁性催化剂的制备。采用XRD、SEM、FT-IR、BET、EDX、TEM、TGA和VSM等多种方法对催化剂进行表征。然后，将鉴定的催化剂用于通过丙二腈、醛和二甲酮、4-羟基香豆素或 2-萘酚在 70°C 在无溶剂条件下的反应合成各种色烯骨架。用于确定产物结构的光谱方法包括 13C NMR、1H NMR 和 FT-IR。
• 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.
• Copper‐amine complex immobilized on nano NaY zeolite as a recyclable nanocatalyst for the environmentally friendly synthesis of 2‐amino‐4 <i>H</i> ‐chromenes
  作者：Mohammadreza Azizi Amiri、Ghasem Firouzzadeh Pasha、Mahmood Tajbakhsh、Sakineh Asghari

  DOI：10.1002/aoc.6886

  日期：2022.12

  catalytic activity of the synthesized nano-sample was evaluated in a three-component synthesis of 2-amino-4H-chromene derivatives, which resulted in high reaction yields and short reaction times under green conditions. The catalyst is separated by filtration and can be reused for at least seven consecutive runs without significant loss of catalytic activity. The nature of the supported [2-(3-[(2-ami

  通过用 3-氯丙基三甲氧基硅烷 (CPTMS) 和 [2-(3-[(2-氨基乙基)硫代]丙基}硫代)乙基]胺对纳米 NaY 沸石进行后改性制备纳米 NaY 沸石负载的铜-胺络合物然后与Cu（I）离子配位。各种技术，如傅里叶变换红外光谱 (FT-IR)、X 射线粉末衍射 (XRD)、动态光散射 (DLS)、热重分析 (TGA)、差热分析 (DTA)、扫描电子显微照片 (SEM)、透射电子显微镜 （TEM)、Brunauer-Emmett-Teller (BET)、t-plot、能量色散光谱 (EDS)、电感耦合等离子体 (ICP) 和元素分析用于表征合成催化剂的结构。合成的纳米样品的催化活性在 2-氨基-4 H的三组分合成中进行了评估-色烯衍生物，在绿色条件下产生高反应产率和短反应时间。催化剂通过过滤分离，可重复使用至少七次连续运行而不会显着损失催化活性。沸石表面负载的 [2-(3-[(