N-benzyl-4-(methylthio)-3-nitro-4H-chromen-2-amine | 897407-09-9

• 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-benzyl-4-(methylthio)-3-nitro-4H-chromen-2-amine
• 英文别名: N-benzyl-N-[4-(methylsulfanyl)-3-nitro-4H-2-chromenyl]amine；N-benzyl-4-(methylthio)-3-nitro-4h-chromen-2-amine；N-benzyl-4-methylsulfanyl-3-nitro-4H-chromen-2-amine
• CAS: 897407-09-9
• 化学式: C₁₇H₁₆N₂O₃S
• 分子量: 328.392
• InChiKey: ZQYNEFPNXKXEAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-苯基哌啶 、 N-benzyl-4-(methylthio)-3-nitro-4H-chromen-2-amine 以 乙醇 为溶剂， 反应 15.0h， 以74%的产率得到
  参考文献：
  名称：

  Synthesis, in vitro and in silico anti-proliferative activity of 4-aryl-4H-chromene derivatives

  摘要：

  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.

  DOI：

  10.1007/s00044-016-1569-z
• 作为产物：
  描述：

  (E)-1-苄基氨基-1-(甲硫基)-2-硝基乙烯 、 水杨醛 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 21.17h， 以81%的产率得到N-benzyl-4-(methylthio)-3-nitro-4H-chromen-2-amine
  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 of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes
  作者：H. Surya Prakash Rao、K. Geetha、M. Kamalraj

  DOI：10.1016/j.tet.2011.08.045

  日期：2011.10

  A combinatorial library of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes was synthesized in high yield by C4-SMe substitution in N-alkyl/phenyl 4-(methylthio)-3-nitro-4H-chromen-2-amines with a variety of phenols. The reaction always provided C2 substitution in the phenol ring, dictated by hydrogen bond interactions between the phenolic hydroxyl group and the nitro group in 3-nitro-4H-chromenes. Reduction of the nitro group with concomitant hydrolysis of the enamine in 4-(2-hydroxyaryl)-3-nitro-4H-chromenes with Zn, Ac(2)O in AcOH furnished hybrid amino-acid lactone incorporating ortho-tyrosine and phenyl alanine moieties. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• 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.
• Nitroketene acetal chemistry: efficient synthesis of 2-amino-3-nitro-4H-chromenes
  作者：H. Surya Prakash Rao、K. Geetha

  DOI：10.1016/j.tetlet.2009.04.018

  日期：2009.7

  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.