N-[6-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine | 1173429-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-[6-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine
• 英文别名: 6-methoxy-N-methyl-4-(methylthio)-3-nitro-4H-chromen-2-amine；6-methoxy-N-methyl-4-methylsulfanyl-3-nitro-4H-chromen-2-amine
• CAS: 1173429-47-4
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: MJUOHVSDUCRWNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-羟基-1,4-萘醌 、 N-[6-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine 以 乙醇 为溶剂， 反应 0.25h， 以96%的产率得到2-hydroxy-3-(6-methoxy-2-(methylamino)-3-nitro-4H-chromen-4-yl)naphthalene-1,4-dione
  参考文献：
  名称：

  2-羟基萘-1,4-二酮和4 H-色烯共轭物的合成及抗菌性能评价

  摘要：

  通常将4 H -Chromene和1,4-萘醌系统视为具有医学特权的支架。我们设计了结合了这两种支架的新型结合物，因为这种结合物表现出独特的生物学特性，反映出由于单个单元和集体存在而产生的生物学特性。在这项工作中，我们已经从容易获得的2-烷基氨基-4-甲基硫烷基-3-硝基-4 H-色烯和2-羟基萘-1,4-二酮中轻松，高效且高收率地合成了19种此类共轭物。高极性nitroketene- Ø，ñ存在于缀合物中的β-乙缩醛单元被设计为防止穿过血脑屏障。我们已经进行了结构活性关系（SAR）研究，该研究基于对三种革兰氏阳性细菌[枯草芽孢杆菌，金 黄色葡萄球菌（MSSA），金黄色葡萄球菌（MRSA）]，一种革兰氏阴性细菌（大肠杆菌）的十种结合物进行初步抗菌筛选的研究）和两种真菌（黑曲霉，白色念珠菌）。SAR研究表明，在4 H的C（6）和C（8）位置具有卤素的共轭物具有C（2）NMe基团的-色烯环显示

  DOI：

  10.1007/s11164-016-2536-5
• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 (E-)-N-methyl-1-(methylthio)-2-nitroethanamine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以85%的产率得到N-[6-methoxy-4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]-N-methylamine
  参考文献：
  名称：

  Nitroketene acetal chemistry: efficient synthesis of 2-amino-3-nitro-4H-chromenes

  摘要：

  Base-catalyzed reaction of the nitroketene N,S-acetals and the ring substituted 2-hydroxybenzaldehydes afforded a combinatorial library of the 2-alkylamino-3-nitro-4-alkylsulfanyl 4H-chromenes in excellent yields. Nucleophilic displacement of the C4 alkylsulfanyl group with different thiols afforded 4H-chromenes with structural diversity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.018

文献信息

• Synthesis, in vitro and in silico anti-proliferative activity of 4-aryl-4H-chromene derivatives
  作者：A. Parthiban、M. Kumaravel、J. Muthukumaran、R. Rukkumani、R. Krishna、H. Surya Prakash Rao

  DOI：10.1007/s00044-016-1569-z

  日期：2016.7

  A new series of C4-N,N-dialkylaniline-substituted 4-aryl-4H-chromenes were synthesized, and their anti-proliferative properties were evaluated against human cancer cell lines, namely, laryngeal carcinoma (Hep2), lung adenocarcinoma (A549), and cervical cancer (HeLa). The best among them, the 4-aryl-4H-chromene with C4-1-phenylpiperidine substitution was selected for further structure activity relationship (SAR) studies. Among the derivatives, N,6-dimethyl-3-nitro-4-(4-(piperidine-1-yl)phenyl)-4H-chromene-2-amine 3k showed most potent cytotoxic activity against all three cancer cell lines. Toxicity studies revealed that the 4-aryl-4H-chromenes specifically target the cancer cell lines. Molecular docking studies of this compound revealed its efficient interaction with the active site of alpha beta-tubulin protein.
• Synthesis, in vitro and in silico antimalarial activity of 7-chloroquinoline and 4H-chromene conjugates
  作者：A. Parthiban、J. Muthukumaran、Ashan Manhas、Kumkum Srivastava、R. Krishna、H. Surya Prakash Rao

  DOI：10.1016/j.bmcl.2015.08.030

  日期：2015.10

  A new series of chloroquinoline-4H-chromene conjugates incorporating piperizine or azipane tethers were synthesized and their anti-malarial activity were evaluated against two Plasmodium falciparum strains namely 3D7 chloroquine sensitive (CQS) and K1 chloroquine resistant (CQR). Chloroquine was used as the standard and also reference for comparison. The conjugates exhibit intense UV absorption with lambda(max) located at 342 nm (log epsilon = 4.0), 254 nm (log epsilon = 4.2), 223 nm (log epsilon = 4.4) which can be used to spectrometrically track the molecules even in trace amounts. Among all the synthetic compounds, two molecules namely 6-nitro and N-piperazine groups incorporated 7d and 6-chloro and N-azapane incorporated 15b chloroquinoline-4H-chromene conjugates showed significant anti-malarial activity against two strains (3D7 and K1) of P. falciparum. These values are lesser than the values of standard antimalarial compound. Molecular docking results suggested that these two compounds showing strong binding affinity with P. falciparum lactate dehydrogenase (PfLDH) and also they occupy the co-factor position which indicated that they could be the potent inhibitors for dreadful disease malaria and specifically attack the glycolytic pathway in parasite for energy production. (C) 2015 Elsevier Ltd. All rights reserved.