1-(4-Acetyl-phenyl)-3,3-bis-methylsulfanyl-propenone | 136152-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-Acetyl-phenyl)-3,3-bis-methylsulfanyl-propenone
• CAS: 136152-76-6
• 化学式: C₁₃H₁₄O₂S₂
• 分子量: 266.385
• InChiKey: ZXCIMTXUDNLGHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  alpha-氰基-邻-苯乙腈 、 1-(4-Acetyl-phenyl)-3,3-bis-methylsulfanyl-propenone 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以50%的产率得到3-(4-acetylbenzoyl)-4-amino-2-(methylthio)-1-naphthonitrile
  参考文献：
  名称：

  Base mediated synthesis of α-aminated aroyl/acetylnaphthalenes through [4+2] annulations

  摘要：

  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.

  DOI：

  10.1016/j.tet.2014.09.089
• 作为产物：
  描述：

  二硫化碳 、 1,4-二乙酰苯 、 碘甲烷 在 sodium hydride 作用下， 生成 1-(4-Acetyl-phenyl)-3,3-bis-methylsulfanyl-propenone
  参考文献：
  名称：

  Infrared spectra and theoretical study of the conformations of substituted benzoylketene-S,S-acetals

  摘要：

  The C=O stretching frequencies of substituted benzoylketene-S,S-dimethylacetals (1a-1o) and benzoylketene-S,S-ethyleneacetals (2a-2m) were measured in CHCl3 and CCl4 and correlated with the Hammett substituent constants. The correlations were split into two different and well separated lines for compounds containing electron donor and electron acceptor substituents, which were assigned to s-trans and s-cis quasiplanar conformations. The correlations of carbonyl stretching frequencies with C=O bond orders and oxygen atom charge densities calculated using the semiempirical AM1 method reveal similar results consistent with assignments of structures 1 and 2 to two quasiplanar conformations. The preparation of some new benzoylketene-S,S-acetals is reported as well.

  DOI：

  10.1007/bf00811088

文献信息

• 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.