3-(4-nitrophenyl)-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-(4-nitrophenyl)-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 英文别名: 3-(4-Nitrophenyl)-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 化学式: C₂₁H₁₃NO₅
• 分子量: 359.338
• InChiKey: LAHAOXZYTURRBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methoxyphenyl 3-phenylpropiolate 在 碘 、 palladium diacetate 、 碳酸氢钠 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-(4-nitrophenyl)-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  Design, synthesis and anticancer properties of novel oxa/azaspiro[4,5]trienones as potent apoptosis inducers through mitochondrial disruption

  摘要：

  A series of twenty seven oxa/azaspiro[4,5]trienone derivatives were synthesized and their anticancer properties have been explored. GI(50) values of all these compounds were evaluated against four types of human cancer cell lines, i.e. MCF-7 (breast), DU-145 (prostate), A549 (lung) and HepG2 (liver). Five compounds of the series exhibited good anticancer potential against MCF-7 with GI(50) values less than 2 mu M. Detailed biological studies of the two representative compounds 9b and 9e revealed that they arrest cell cycle in G0/G1 phase and induce mitochondria mediated apoptosis, that was further confirmed by measurement of mitochondrial membrane potential (Delta Psi m), intracellular ROS generation, caspase 9 activity and Annexin V-FITC assay. Furthermore, western blot analysis suggested that these compounds up-regulate the levels of p53, p21, p27 and Bax, and down-regulate the level of Bcl-2 confirming the apoptosis inducing properties. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.050

文献信息

• Intramolecular ipso-arylative cyclization of aryl-alkynoates and N-arylpropiolamides with aryldiazonium salts through merged gold/visible light photoredox catalysis
  作者：Avinash H. Bansode、Samir R. Shaikh、Rajesh G. Gonnade、Nitin T. Patil

  DOI：10.1039/c7cc04010e

  日期：——

  A visible-light-promoted merged gold/photoredox catalyzed ipso-arylative cyclization has been reported. For instance, the reaction of aryl-alkynoates and N-arylpropiolamides with aryldiazonium salts in the presence of catalytic amounts of [(4-OCH3)C6H4]3PAuCl and Ru(bpy)3(PF6)2 under irradiation using a 32 W CFL bulb gave arylated spirocarbocycles in moderate to good yields.

  可见光促进的合并金/ photoredox催化IPSO -arylative环化的报道。例如，芳基和alkynoates的反应Ñ与芳基重氮盐-arylpropiolamides在催化量的[（4-OCH存在3）C 6 H ^ 4 ] 3 PAuCl和Ru（联吡啶）3（PF 6）2下照射使用32 W CFL灯泡可获得中等至良好收率的芳基化螺碳环化合物。
• Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells
  作者：Sivakumar Archana、Ramasatyaveni Geesala、Narasimha B. Rao、Suresh Satpati、Giridhar Puroshottam、Akhila Panasa、Anshuman Dixit、Amitava Das、Ajay Kumar Srivastava

  DOI：10.1016/j.bmcl.2014.11.077

  日期：2015.2

  An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-alpha) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines-ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC50 values less than 6.5 mu M which corroborate the results of molecular docking studies. (C) 2014 Elsevier Ltd. All rights reserved.