6-氯-5-[(4-硝基苯基)二氮烯基]嘧啶-2,4-二胺 | 88290-57-7

• 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: 6-氯-5-[(4-硝基苯基)二氮烯基]嘧啶-2,4-二胺
• 英文名称: 2,6-diamino-4-chloro-5-(p-nitrophenylazo)pyrimidine
• 英文别名: 6-Chloro-5-[(E)-(4-nitrophenyl)diazenyl]pyrimidine-2,4-diamine；6-chloro-5-[(4-nitrophenyl)diazenyl]pyrimidine-2,4-diamine
• CAS: 88290-57-7
• 化学式: C₁₀H₈ClN₇O₂
• 分子量: 293.672
• InChiKey: LQLOQCXBVZJFLH-UHFFFAOYSA-N

物化性质

• 沸点：
  654.4±65.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氧酰肼-2H-1-苯并吡喃-3-羧酸 、 6-氯-5-[(4-硝基苯基)二氮烯基]嘧啶-2,4-二胺 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到N’-(2,6-diamino-5-((4-nitrophenyl)diazenyl)pyrimidin-4-yl)-2-oxo-2H-chromene-3-carbohydrazide
  参考文献：
  名称：

  用于生物成像的香豆素和苯并香豆素衍生物共轭嘧啶支架的合成及荧光性质

  摘要：

  合成了一系列香豆素和5,6-苯并甲基豆香素取代的嘧啶衍生物11 – 15和22 – 25，旨在开发新的成像荧光剂。类似地，在MWI条件下用香豆素3-碳酰肼5处理4-氯嘧啶类似物16，然后用NH 4 OAc在HOAc中沸腾，得到香豆素-1,2,4-三唑并嘧啶类似物18。以罗丹明6G为标准染料，在MeOH中用分光光度法研究了荧光性质。所有化合物均在331至495 nm之间显示出发射。所有化合物的量子产率被发现是弱，除了甲基苯并香豆素-3-羧酸乙酯22其显示（Φ ˚F 相比罗丹明6G作为标准（Φ= 0.98）˚F  = 0.95）。 香豆素和苯并香豆素衍生物共轭嘧啶支架的合成及其荧光性质，用于生物成像应用。纳吉·A·马苏迪（Najim A.

  DOI：

  10.1007/s10895-015-1677-z
• 作为产物：
  描述：

  4-硝基苯胺 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 生成 6-氯-5-[(4-硝基苯基)二氮烯基]嘧啶-2,4-二胺
  参考文献：
  名称：

  分子内电荷转移和核量子效应对偶氮嘧啶中分子内氢键的影响

  摘要：

  通过核磁共振波谱法和涉及核量子效应的DFT计算研究了5-偶氮嘧啶中的分子内氢键（IMHBs）。通过偶氮偶合制备一系列具有一个或两个能够与偶氮基形成IMHB的氢键供体的取代的5-苯基偶氮嘧啶。化合物的两个旋转异构体与两个可能的IMHBs之间的互变壁垒是通过可变温度NMR光谱法确定的，证明了该壁垒受到分子内电荷转移的显着影响。通过氢键的标量耦合研究在15N标记的化合物和IMHBs的稳定性与实验NMR参数相关联，并通过涉及核量子效应的路径积分分子动力学模拟得以合理化。通过比较实验数据和计算得出的NMR数据，可以获得氢-氘同位素交换时氢键几何结构的详细信息。

  DOI：

  10.1021/acs.joc.7b01810

文献信息

• Synthesis and Modeling Study of Some Potential Pyrimidine Derivatives as HIV Inhibitors
  作者：Najim A. Al-Masoudi、Yossra A. Marich、Niran J. Al-Salihi、Bahjat Saeed

  DOI：10.5560/znb.2014-4107

  日期：2014.8.1

  ine derivatives 4 - 13 and 2,6-diamino-5-arylazo-4-chloro-pyrimidine analogs 15 - 20 were synthesized from the pyrimidine scaffolds 3 and 14, respectively, via diazotization with various amines. Nucleophilic displacement at the 2,4-diamino-5-arylazo-6-chloro-pyrimidine 16 by different amines afforded the 4-alkylamino analogs 21 - 27. All new compounds were evaluated for their in vitro anti-HIV activity

  合成了一系列新的 2-amino-6-((4-aryldiazenyl)benzyloxy)-4-chloropyrimidine 衍生物 4-13 和 2,6-diamino-5-arylazo-4-chloro-pyrimidine 类似物 15-20嘧啶支架 3 和 14，分别通过与各种胺的重氮化。2,4-diamino-5-arylazo-6-chloro-pyrimidine 16 上的 2,4-diamino-5-arylazo-6-chloro-pyrimidine 16 被不同的胺亲核置换得到 4-烷基氨基类似物 21 - 27。 评估了所有新化合物在 MT-4 中的体外抗 HIV 活性在我们之前工作的基础上，将细胞作为非核苷逆转录酶抑制剂。筛选结果表明，10 和 11 是该系列中唯一抑制细胞培养物中 HIV-1 复制的化合物，EC50 >1:23 和 >2:92 μg mL-1，CC50
• <p>Evaluation of novel pyrimidine derivatives as a new class of mushroom tyrosinase inhibitor</p>
  作者：S Shohreh Mirmortazavi、Mahdieh Farvandi、Hossein Ghafouri、Asadollah Mohammadi、Mostafa Shourian

  DOI：10.2147/dddt.s209324

  日期：——

  Background and aim: Tyrosinase (EC 1.14.18.1) is responsible for enzymatic browning in fruits and vegetables. Its inhibitors may be applied to efficiently treat hyperpigmentation and are widely used in pharmaceutical and cosmetic products, food supplements and insecticides. Previous studies have shown that heterocyclic compounds with an amino group can inhibit tyrosinase activity. The present study aims to evaluate the inhibitory effect of some novel 2,6-diamino-4-chloropyrimidine derivatives (la-e) and 2,4,6-triaminopyrimidine (2a-e) including bioactive aniline moiety on the activity of the mushroom tyrosinase.Methods: In practice, the azo salt was initially synthesized from aniline derivatives and combined subsequently with the 2,4,6-triaminopyrimidine and 2,6-diamino-4 chloropyrimidine followed by crystallization. The structures of resulting compounds were confirmed by FT-IR, C-13 NMR, and H-1 NMR. The derivatives (0-100 mu M) were evaluated for their inhibitory effect on tyrosinase activity using 1-3,4-dihydroxyphenylalanine (1-DOPA) as substrate.Results: All compounds showed inhibitory effects against the activity of the enzyme. About 23.72-55.08% inhibition was observed in the presence of 30 mu M of each compound. The IC50 values of the synthesized compounds were measured, and their inhibition properties were also visualized by zymography. Based on the results, the compounds 1a-e and 2a-e showed moderate inhibitory activities. Notably, pyrimidine derivatives 1a (IC50=24.68) and 1d (IC50=24.45) also exhibited similar inhibitory activities when compared with the positive control, kojic acid (IC50=25.24 mu M). Kinetic studies indicated that the type of inhibition was noncompetitive.Conclusion: All results suggest that pyrimidine derivatives, especially 1d and 1a, can be considered as safe and efficient tyrosinase inhibitors.
• Influence of Intramolecular Charge Transfer and Nuclear Quantum Effects on Intramolecular Hydrogen Bonds in Azopyrimidines
  作者：Kateřina Bártová、Lucie Čechová、Eliška Procházková、Ondřej Socha、Zlatko Janeba、Martin Dračínský

  DOI：10.1021/acs.joc.7b01810

  日期：2017.10.6

  Intramolecular hydrogen bonds (IMHBs) in 5-azopyrimidines are investigated by NMR spectroscopy and DFT computations that involve nuclear quantum effects. A series of substituted 5-phenylazopyrimidines with one or two hydrogen bond donors able to form IMHBs with the azo group is prepared by azo coupling. The barrier of interconversion between two rotamers of the compounds with two possible IMHBs is

  通过核磁共振波谱法和涉及核量子效应的DFT计算研究了5-偶氮嘧啶中的分子内氢键（IMHBs）。通过偶氮偶合制备一系列具有一个或两个能够与偶氮基形成IMHB的氢键供体的取代的5-苯基偶氮嘧啶。化合物的两个旋转异构体与两个可能的IMHBs之间的互变壁垒是通过可变温度NMR光谱法确定的，证明了该壁垒受到分子内电荷转移的显着影响。通过氢键的标量耦合研究在15N标记的化合物和IMHBs的稳定性与实验NMR参数相关联，并通过涉及核量子效应的路径积分分子动力学模拟得以合理化。通过比较实验数据和计算得出的NMR数据，可以获得氢-氘同位素交换时氢键几何结构的详细信息。
• Synthesis, and Fluorescence Properties of Coumarin and Benzocoumarin Derivatives Conjugated Pyrimidine Scaffolds for Biological Imaging Applications
  作者：Najim A. Al-Masoudi、Niran J. Al-Salihi、Yossra A. Marich、Timo Markus

  DOI：10.1007/s10895-015-1677-z

  日期：2015.11

  6-benzomcomarin substituted pyrimidine derivatives 11–15 and 22–25 were synthesized, aiming to develop new imaging fluorescent agents. Analogously, treatment of 4-chloropyrimidine analog 16 with coumarin 3-carbohyrazide 5 under MWI condition followed by boiling with NH4OAc in HOAc furnished coumarin-1,2,4-triazolo-pyrimidine analog 18. The fluorescence property was investigated spectrophotometrically in

  合成了一系列香豆素和5,6-苯并甲基豆香素取代的嘧啶衍生物11 – 15和22 – 25，旨在开发新的成像荧光剂。类似地，在MWI条件下用香豆素3-碳酰肼5处理4-氯嘧啶类似物16，然后用NH 4 OAc在HOAc中沸腾，得到香豆素-1,2,4-三唑并嘧啶类似物18。以罗丹明6G为标准染料，在MeOH中用分光光度法研究了荧光性质。所有化合物均在331至495 nm之间显示出发射。所有化合物的量子产率被发现是弱，除了甲基苯并香豆素-3-羧酸乙酯22其显示（Φ ˚F 相比罗丹明6G作为标准（Φ= 0.98）˚F  = 0.95）。 香豆素和苯并香豆素衍生物共轭嘧啶支架的合成及其荧光性质，用于生物成像应用。纳吉·A·马苏迪（Najim A.