4-amino-2-methylsulfanyl-3-(naphthalene-1-carbonyl)naphthalene-1-carbonitrile | 1616775-90-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4-amino-2-methylsulfanyl-3-(naphthalene-1-carbonyl)naphthalene-1-carbonitrile
• 英文别名: 4-Amino-2-methylsulfanyl-3-(naphthalene-1-carbonyl)naphthalene-1-carbonitrile
• CAS: 1616775-90-6
• 化学式: C₂₃H₁₆N₂OS
• 分子量: 368.459
• InChiKey: NPNHTYFZIRQQEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-萘乙酮 、 2-(1-cyano-2,2-bis-methylsulfanylvinyl)benzonitrile 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以48%的产率得到4-amino-2-methylsulfanyl-3-(naphthalene-1-carbonyl)naphthalene-1-carbonitrile
  参考文献：
  名称：

  合成1-氨基-2-芳酰基/ acetylnaphthalenes通过碱介导的一种罐间和分子内的C-C键形成的策略†

  摘要：

  在碱性条件下，通过2-氰基甲基苄腈，二硫化碳和甲基碘的反应，合成了一种新的前体2-（1-氰基-2,2-双（甲硫基）乙烯基）苄腈。2-（1-氰基-2,2-双（甲硫基）乙烯基）苄腈与各种官能化的芳基/杂芳基甲基酮或丙酮在碱性条件下反应，得到4-氨基-3-芳酰基/杂芳酰基/乙酰基-2-甲基硫烷基萘通过（5C + 1C）环化策略获得高产率的-1-腈; 这涉及顺序的分子间，然后是分子内的CC键形成反应。产物的结构通过单晶X射线晶体学确认。

  DOI：

  10.1039/c4ob00432a

文献信息

• Base mediated synthesis of α-aminated aroyl/acetylnaphthalenes through [4+2] annulations
  作者：Surjeet Singh、Ismail Althagafi、Pratik Yadav、Rahul Panwar、Abhinav Kumar、Ramendra Pratap

  DOI：10.1016/j.tet.2014.09.089

  日期：2014.11

  We have developed a base promoted simple, efficient and alternative approach for the synthesis of 4-amino-3-aroyl//heteroaroyl/acetyl-2-methylsulfanyl-naphthalene-1-carbonitriles by reaction of easily accessible 3,3-bis(methylthio)-1-aryl/heteroaryl/acetylprop-2-en-1-one and 2-cyanomethyl-benzonitrile. Reaction of 1-(2-halo/methoxy-phenyl)-3,3-bis(methylthio)prop-2-en-1-one and 2-cyanomethylbenzonitrile under basic conditions also afforded 6-(methylthio)-7-oxo-7,12-dihydrobenzo[c]acridine-5-carbonitrile along with usual product. Structure of the synthesized product has been confirmed by single X-ray crystallography. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, biological evaluation and molecular docking study of 1-amino-2-aroylnaphthalenes against prostate cancer
  作者：Reeta Rai、Roshan Kumar Dutta、Surjeet Singh、Dharmendra Kumar Yadav、Seema Kumari、Harpreet Singh、Rinkoo Devi Gupta、Ramendra Pratap

  DOI：10.1016/j.bmcl.2018.03.057

  日期：2018.5

  A series of functionalized naphthalene was synthesized and screened against human prostate cancer cell line (PC-3). The in vitro antiproliferative activity of the synthesized compounds was evaluated by monitoring their cytotoxic effects against PC-3 cells by using MTT assay. We observed that compound 5f resulted in more than 50% cell death at 14 mu M. Treatment of PC-3 cells with 5f provides apoptosis by flow cytometry. Western blotting showed decreased expression of pro-caspase 8 and 9. Our study shows that cancer cell treated with 5f has higher concentration of reactive oxygen species as compare to untreated sample, which facilitate cancerous cell to enter apoptosis. Exact mechanism by which ROS is generated after 5f treatment is still under study. Molecular docking study further strengthens the results obtained from in vitro experiments. Compound 5f can be considered as a promising leads for anticancer agent against prostate cancer cells due to its potent cytotoxic activity and apoptotic effect. (C) 2018 Elsevier Ltd. All rights reserved.